Vacation Rentals By Owner In Chicago, IL

Feel at Home, Unwind, and Enjoy the amenities you deserve at our Michigan Ave Penthouse with 6 combined units!brbrGuests love staying with us because:br-Central Location on Grant Park (no car needed!)br-10 Bedrooms with Queen beds!br-FAST WIFIbr-En-suite Laundry in all unitsbr-Did we mention the Lake & Park are outsidet the front door br-Shared Rooftop Deck stunning viewsbr-Gymbr-3 blocks from Red `L` subwaybr-Close to Grant Park, The Bean, MuseumsbrbrYou won`t find many properties like this in ChicagobrbrThis is a combination listing: brR24000114149brR22000082721brR22000082722brR22000081989brR22000081990brR22000081987brbrA manicured park. Waves crashing along the Lake Michigan. brbrWhen you`re here, you`re given a bird’s eye view of Chicago’s Front Yard, or more commonly known as Grant Park. brbrDrop your bags in your private space, complete with cozy beds, sky-high ceilings, and expansive windows allowing sunlight to pour in. brbrMake your way to the fitness center for a quick workout and then grab a breath of fresh air on the rooftop. brbrYou get to choose from one of the 6 condos on this floor to stay in. brbrTime to hit the pavement. Saunter the art-filled halls at the Art Institute of Chicago. Wander past the 19th-century mansions on Prairie Avenue. Then fill your belly at The Dearborn (we recommend the mouth-watering fish and chips). Trade your sneakers for your go-to night-out pair. Let your ears guide you to the bustling bars. Try a new cocktail. Or order a pint and join the locals as they cheer on the Cubs. br brWorking, relaxing, living. Our spaces have all the other essentials you need for your stay. br br- Contact-free check-in - Super-fast WiFibr- Fresh towels and bathroom essentials - Pre-cleaning before your arrivalbr- Plenty of space to workbr- HDMI cord for streamingbr- Fitness centerbr- Rooftopbr- En-suite laundrybr- Fully equipped kitchenbr- Sleeper sofabrYou access the property on Michigan Avenue. You are given a PIN or virtual key to access the front door.brbrOnce you get inside the building, you walk all the way back to the service elevator because it is the only elevator that takes you to the 12th floor Penthouse floor.brbrOnce to the floor, you can choose from our 6 condos on the floor. Enjoy!brbrYou have private, full access to the 6 units on the floor, the shared rooftop, and the shared gymbrbrWe`re always here to help as needed.brbrThe South Loop is such a dynamic mix of attractions and histories that the neighborhood tends to be seen as many different things to many different people. Consider the assorted areas that comprise the South Loop:brbrMuch of its eastern edge is encompassed by the Museum Campus, an impressive collection of cultural treasures that includes the Field Museum, Adler Planetarium and Shedd Aquarium. This campus sits on scenic lakefront parklands that are an extension of Grant Park. With 319 acres of green space and recreational fields, Grant Park is known as `Chicago`s front yard` to locals and also plays host to major city events such as Taste of Chicago, Chicago Blues Festival and Lollapalooza.brbrJutting out further into Lake Michigan is Northerly Island, a peninsula sought out by nature lovers, while along the southern edge the sports fans know Soldier Field as the stadium for the beloved Chicago Bears football team. Meeting attendees are most familiar with McCormick Place, the largest convention center in the country, which is also in the immediate area.brbrAnd yet there are even more facets to the South Loop. History buffs point out the Motor Row District along South Michigan Avenue and nearby Prairie Avenue District, the `Millionaire`s Row` that was lined with mansions belonging to Chicago`s most wealthy elite during the end of the 19th century.brbrIn the adjacent Printer`s Row neighborhood, urban loft condos now fill the commercial spaces in what was formerly the center of the Midwest`s publishing industry. Connections to this past are still seen within the venerable, independent book store and annual summer lit fest here. But business professionals and students have brought new life and redevelopment (though the vibe remains mellow), filling the restaurants, music clubs, smaller theaters and museums that have all established themselves in the community.brbrWe are very central and in close walking distance to the subway stops at Roosevelt and Harrison. We recommend NOT renting a car, and walking, ubering, and using public transit for your stay.brbr*There is a flight of stairs to access the elevatorbrbr❎No Local Guests (City or Suburbs)br Quiet hours: 10pm to 8ambr Minimum age of 30 to bookbrbr Last-Minute Bookings PolicybrTo ensure a smooth check-in, all same-day reservations will REQUIRE HOST APPROVAL. Please message us first so we can confirm and ensure everything is set for your arrival. This helps us make sure the space is properly prepared and ready for your stay.brbrThe base price for this home is for 14 guests only. There will be an extra guest fee of $10 per guest per night if your group exceeds to 14 people. br brSmall Pet Fee (Under 20lbs, No shedding) - $250brLarge Pet Fee (Over 20lbs) - $300 plus a $200 refundable security deposit and subject to host approval. brIf the pet sheds, we will require an additional $150 refundable Security deposit.brUnauthorized Pets - $250 plus any damages or additional cleaning costs incurredbrbrUnauthorized Late Check Out -Up to the cost of any impacted nights subsequent to originally scheduled check-out brSmoking in Room/Common Area - $500.00 minimum charge and eviction from Rental Unit brExcessive Cleaning - Up to $125.00 per hour of additional cleaning needed brDamaged or Missing Items - Varies depending on cost of itembrMissing Keys - $50.00 minimum chargebrMissing Fob - $150.00 minimum chargebrbrNoise Complaints: potential warning issued or, if necessary, eviction with no refund and a charge of up to $1,000.00 brParty in Unit or Common Area - Up to $2,000.00 plus any damages to the unit brForgotten Personal Belongings - $75.00 minimum chargebrIf items are left behind and guest wants it mailed back, guest will be charged a $50 trip fee along with the shipping costbr brNo Unauthorized Late Check Out without notice from Host.brIf our cleaners agree to early check-in / check out they charge us (per unit): br-Early check-Ins at 2pm $100 br-Late Check-Outs at noon $100 br brAll guest names and ages must be registered before you are allowed to check in. br brThere is a NOISE MONITORING system within the home to track decibel noise level. Please respect our neighbors and do not get too loud outside quiet hours :)brbrbrQ: Is the neighborhood safe brA: Very much so. 24 hours a day.brbrQ: What about PARKING brA: You may inquire for our private under building parking spot. The spot is $100 flat fee. brbrWe don’t recommend driving because we are so centrally located. You may find a lot or garage nearby for $18-30 / night. There are multiple garages or valet services within 2 blocksbrbrQ: Do I need to bring towels, a hair dryer, or linens brA: Nope! we provide all these things. We also provide you and your guests with a starter pack of toilet papersbrbrQ: When can I check in or check out brA: Check in is 4pm and check out is 10am. Early check ins can be difficult if there are guests who checked out same day. We ask for an early check-in, or a late-check out fee, if you request either.brbrQ: Is the Gym and Rooftop shared brA: Yes, it is shared so please be respectful of other tenants and guests using the space.brbrQ: Luggage Drop-Off / Storage brA: If you do not have flights that coincide with our check-in and checkout times, you may store your bags with Radical Storage near our property. It allows you to store your bags for your optimal time :)brbrQ: Can I come and go as I please brA: Yes. And we wouldn`t trust any listing with which this isn`t the case.brbrQ: Is the place professionally cleaned between guests brA: Yes, and we take pride in providing a clean home for guests.brbrQ: What`s my total booking price brA: We honestly have no idea. With fees included, it only shows the guest how much they pay. This figure should be present after you enter your dates. Note that, pricing varies on a daily basis, and it actually uses some crazy algorithm to adjust it automatically, so I don`t actually control this.brbrQ: Are the beds comfortable brA: Very. Some guests say they`re the best they`ve ever slept on!brbrNo Agency Relationship. Nothing herein contained shall be deemed to authorize or empower either party to act as agent for the other party to this Agreement, or to conduct business in the name, or for the account, of the other party to this Agreement.brbrGuest VerificationbrAs part of our vetting process, we may ask guests to confirm a few details — such as their names, ages, where they’re traveling from, or their travel plans — before accepting a booking. In some cases, we may also request a valid government-issued ID for verification purposes. This helps us ensure that all stays are safe, transparent, and in line with our house policies.brbrUnresponsive GuestbrIn some cases, if a guest does not respond within a reasonable period, we reserve the right to cancel the reservation. brFor same-day bookings, this timeframe is up to 2 hours or less. For all other bookings, this timeframe is up to 8 hours. This ensures that we can provide the best experience and availability for all our guests.brbrOnline Check-In & Rental Agreement RequiredbrBefore receiving check-in instructions, all primary guests must complete our online check-in form and review/sign our rental agreement. This helps verify guest details and ensures a smooth, secure arrival.brbrEXTRA GUEST CHARGEbrThe base price covers 14 guests. For more than 14 guests, there is an extra guest fee of $10 per guest for the full number of nights.brExample: 1 extra guest for a 5-night stay = $10 × 5 nights = $50.brbrRefundable Security Deposit: A $300 refundable security deposit is required and will be `held` or `authorized` (not `charged`) by Chicago Hospitality Club on your card.

Condo

Downtown Mich Ave - 6 Penthouses, Sleep 25

Chicago, Illinois, United States

Bed

Bath

Sleeps

$374.87

4th-floor unit with four flights of stairs.brbrBright and spacious apartment in Chicago’s West Ridge neighborhood. Just over a block away from restaurants, bars, cafes, shopping, and local attractions. Start your day with breakfast at Cozy Corner Restaurant, one of our favorites! Enjoy nearby Warren Park and a museum within a 5–10 minute walk. Only a 7-minute walk to the Rogers Park train station for easy public transit access.brbrThe spacebrWelcome to the Windy City! Our cozy chic 2 bed/2 bath is professionally designed and fully furnished for your comfort! You’ll have access to WiFi, a full kitchen, TV and everything you need to enjoy your extended stay in our gorgeous city.brbrWhether you’re visiting Chicago for business or vacation, we’d love to host you!brbrGuest accessbrYou’ll have private access the the entire unit during your stay!brbrOther things to notebrThere are 4 flights up stairs leading up to the apartment.brbrWe do not have designated parking but free street parking is available in the neighborhood. That said, please take care to read any signs indicating no parking or tow zones to avoid any issues. Parking availability can fluctuate depending on the time of day, and if you arrive later in the evening, there’s a chance that spots might be harder to find.brbrIn case you run into this situation, we suggest using the SpotHero app or ParkWhiz to easily locate an affordable and convenience parking spot nearby.brbr**HOUSE RULES**brbrWe want you to have a comfortable and enjoyable stay! To help keep the space safe, clean, and pleasant for everyone, please review and follow the house rules below. Failure to comply may result in cancellation or additional charges.brbrShoes off, please. Kindly remove shoes upon entering the unit.brbrNo smoking anywhere inside the unit or on the property. Smoking will result in immediate cancellation and a $200 damage fee.brbrNo drugs, including marijuana.brbrNo illegal activities anywhere on the property.brbrNo parties or events.brbrNo outside visitors.brbrNo overnight guests without prior approval from the host.brbrFood storage: Please store all food in designated areas and do not leave food out to help prevent pests.brbrKitchen use: Feel free to use the kitchen, but please clean up after yourself. Wash dishes, wipe counters, stove, and microwave. No dirty dishes left in the sink overnight.brbrDamages: If anything is broken or damaged, please let us know right away so we can arrange repair or replacement.brbrCheckout cleaning:brPlease wash dishes, return moved furniture to its original place, and take out the trash before checkout.brThe standard cleaning fee covers normal turnover cleaning. If the unit is left excessively dirty (dirty dishes, trash left throughout the unit, etc.), an additional cleaning fee of up to $100 may apply.brbrTowels & linens: Provided for your entire stay. If you need extras, please let us know in advance. A $50 fee applies to cover the cleaner’s trip. Paid laundry facilities are available in the building.brbrLost keys: A $300 fee applies for lock and key replacement. Please note that lost keys cannot be replaced immediately, and you may temporarily lose access to the unit and building amenities.brbrQuiet hours: Please observe quiet hours from 10:00 PM – 8:00 AM.brbrLate checkout: Checkout time is 11:00 AM. Late checkout without prior approval will incur a $50 fee, which covers the cleaner’s waiting time.brbrThank you for your understanding and cooperation -we truly appreciate it and look forward to hosting you!

Comfy and Chic Escape 2BR and 2BA in Little India

Chicago, Illinois, United States

Bed

Bath

Sleeps

$586.11

This unit is a shorter walk to Wrigley Stadium than a home run.brbrCatty-corner to Wrigley Field, you'll be at the center of all the action while also enjoying a cozy, peaceful getaway.brbrRecently renovated, our unit has all the comforts you'll need and experienced Hosts to welcome you to Wrigley.brbrWe live in the unit below and are always available to you. :-)brbr3 Bedroom(2 queen beds, 2 XL twin beds), 2 bath with laundry in unit. Fully renovated condo with new appliances. Free parking on site. brbrPLEASE NOTE: This unit is at the hub of Wrigley with quick access to the stadium, numerous restaurants, bars, theaters and event spaces.brbrThis means you may hear some city noises on lively nights. These noises are random and very light, but those who are sensitive to noises may not be suitable for this unit.

Shorter Walk To Wrigley Than A Home Run

Chicago, Illinois, United States

3

Bed

Bath

6

Sleeps

$487.24

Summary:brbrWelcome to your Chicago escape! brbrbrbr- Spacious living area, perfect for relaxation or remote work brbr- Fully equipped kitchen for culinary endeavors brbr- In-unit laundry facilities brbr- Access to community gym brbr- Complimentary parking space brbr- Explore local restaurants, beaches, and parks brbrBook your stay with TheDreamRentals today!brbrbrbrThe Space:brbrThe apartment features a well-lit and spacious living area, ideal for relaxation or remote work, complete with comfortable seating. The fully equipped kitchen is prepared for your culinary endeavors, offering all necessary amenities. Two generously sized bedrooms provide a peaceful sanctuary: one with a premium king-size bed and the other with a comfortable queen-size bed. Both contemporary bathrooms are well-equipped with fresh towels, toiletries, and updated fixtures. Additional conveniences include in-unit laundry facilities, access to a community fitness center, and a complimentary parking space.brbrbrbrComfortable Accommodation:brbr- 2 spacious bedroomsbrbr- 2 modern bathroomsbrbr- Premium king-size bed and comfortable queen-size bedbrbrbrbrInterior Feeling:brbr- Well-lit living areabrbr- Comfortable seating for relaxation or workbrbr- Fully equipped kitchen with necessary amenitiesbrbr- Contemporary bathrooms with fresh towels and toiletriesbrbrbrbrOutdoor Bliss:brbr- Access to nearby beaches and parksbrbr- Explore local restaurants within easy reachbrbrbrbrDelightful Dining:brbr- Fully equipped kitchen for culinary adventuresbrbrbrbrProfessional Cleaning:brbr- In-unit laundry facilitiesbrbr- Updated fixtures in bathroomsbrbrbrbrGuest Access:brbrGuests will have access to the entire apartment, including the bedrooms, bathrooms, kitchen, and living areas. Enjoy the convenience of a private entrance and amenities like a washer and dryer.brbrbrbrThe Neighborhood:brbrThe unit is located in Edgewater, a lively and highly walkable North Side Chicago neighborhood known for its easy access to the lake, diverse dining options, and strong transit connectivity. The area offers a mix of quiet residential blocks and vibrant commercial corridors, with the CTA Red Line, multiple bus routes, grocery stores, coffee shops, and international restaurants all just steps away. Residents enjoy being close to the lakefront path, beaches, parks, and everyday conveniences, creating a balanced urban-neighborhood feel that’s popular with young professionals, students, and long-term locals alike.brbrbrbrGetting Around:brbrIt’s easily accessible whether you’re coming by car, train, or bus. The closest CTA Red Line stop is Granville Station, only a short walk away, making it simple to get downtown or anywhere along the North Side. Multiple bus routes run along Broadway, Sheridan, and Ridge, giving plenty of transit options. If driving, the neighborhood is reached via Lake Shore Drive (exit at Bryn Mawr or Hollywood) or Ridge/Clark from the west. Ride-share and biking are also convenient thanks to the area’s dense grid, bike lanes, and overall walkability.brbrbrbrOther Things to Note:brbrTo ensure your stay is as seamless and enjoyable as possible, here are some additional details to keep in mind:brbrbrbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit. brbrbrbrPet Policy: We adore pets, but unfortunately, the penthouse is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the penthouse is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in.brbrbrbrMonitoring: We have camera's outside of the home for your safety. It will be recording during the reservations. Tampering with these will result in a fine.brbrbrbrRegistration number: R25000135401brbrShared Housing Unit Operation License Number: 2823378brbrbrbrInteraction with Guests:brbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.brbrbrbrOur goal is to strike the perfect balance between being available to meet your needs and respecting your desire for a tranquil and enjoyable stay.

Edgewater Apt with Free Parking, Gym, City Living

Chicago, Illinois, United States

Bed

Bath

Sleeps

$504.26

Summary:brbrWelcome to your stylish 2-bedroom apartment in Edgewater, Chicago. brbrbrbr- Spacious bedrooms with king and queen beds brbr- Bright living area with comfortable seating brbr- Fully equipped kitchen for dining at home brbr- In-unit laundry for convenience brbr- Access to community gym brbr- One free garage parking spot brbrbrbrBook your stay with TheDreamRentals today!brbrbrbrThe Space:brbrDiscover your home away from home in this stylish 2-bedroom, 2-bathroom apartment in the heart of Edgewater, Chicago. This property offers a perfect blend of comfort and convenience, making it an ideal choice for travelers seeking a vibrant city experience. Enjoy spacious bedrooms, a bright living area, and a fully equipped kitchen, all designed to make your stay enjoyable and relaxing.brbrbrbrComfortable Accommodation:brbr- 2 bedrooms: One with a king bed and one with a queen bedbrbr- 2 bathrooms with all essentials brbr- Sleeps up to 4 guestsbrbrbrbrInterior Feeling:brbr- Bright living area with comfortable seatingbrbr- Perfect for relaxing or working remotelybrbr- Fully equipped kitchen with all necessary appliancesbrbr- Updated finishes throughoutbrbrbrbrOutdoor Bliss:brbr- Steps from public transitbrbr- Close to local restaurants, beaches, and parksbrbr- Enjoy the vibrant neighborhood atmospherebrbrbrbrDelightful Dining:brbr- Fully equipped kitchen allows for home-cooked mealsbrbr- Dining area for enjoying meals togetherbrbrbrbrProfessional Cleaning:brbr- In-unit laundry for added conveniencebrbr- Access to a community gym for fitness enthusiastsbrbr- One free garage parking spot includedbrbrbrbrGuest Access:brbrGuests will have access to the entire unit!brbrbrbrThe Neighborhood:brbrThe unit is located in Edgewater, a lively and highly walkable North Side Chicago neighborhood known for its easy access to the lake, diverse dining options, and strong transit connectivity. The area offers a mix of quiet residential blocks and vibrant commercial corridors, with the CTA Red Line, multiple bus routes, grocery stores, coffee shops, and international restaurants all just steps away. Residents enjoy being close to the lakefront path, beaches, parks, and everyday conveniences, creating a balanced urban-neighborhood feel that’s popular with young professionals, students, and long-term locals alike.brbrbrbrGetting Around:brbrIt’s easily accessible whether you’re coming by car, train, or bus. The closest CTA Red Line stop is Granville Station, only a short walk away, making it simple to get downtown or anywhere along the North Side. Multiple bus routes run along Broadway, Sheridan, and Ridge, giving plenty of transit options. If driving, the neighborhood is reached via Lake Shore Drive (exit at Bryn Mawr or Hollywood) or Ridge/Clark from the west. Ride-share and biking are also convenient thanks to the area’s dense grid, bike lanes, and overall walkability.brbrbrbrOther Things to Note:brbrWe're thrilled to welcome you to our amazing condo, where luxury and comfort intertwine to create an unforgettable experience. To ensure your stay is as seamless and enjoyable as possible, here are some additional details to keep in mind:brbrbrbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit. Please smoke outside.brbrbrbrPet Policy: We adore pets, but unfortunately, the penthouse is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the penthouse is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in.brbrbrbrMonitoring: We have camera's outside of the home for your safety. It will be recording during the reservations. Tampering with these will result in a fine.brbrbrbrRegistration number: R25000135399brbrShared Housing Unit Operation License Number: 2823378brbrbrbrInteraction with Guests:brbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.brbrbrbrOur goal is to strike the perfect balance between being available to meet your needs and respecting your desire for a tranquil and enjoyable stay.

Chic 2BR Apartment in Edgewater: Gym & Parking

Chicago, Illinois, United States

Bed

Bath

Sleeps

$283.79

Welcome to our cozy and stylish unit in the vibrant Andersonville neighborhood of Chicago! Nestled in the heart of this charming and lively community, your stay will be a perfect blend of comfort, convenience, and local charm.brbrBeyond the neighborhood, Chicago's renowned attractions are just a short distance away. Jump on the nearby CTA train or bus, and within minutes you can find yourself exploring the iconic architecture of the Loop or strolling along the scenic Lake Michigan shoreline!brbrThe space:brThis a large studio unit with anything you might needs for a comfortable stay. When you first walk in you are greeted by an expansive living room with a large sectional sofa. Near the living area is also a designated workspace with a large desk, mirror and cushioned lounge chair. Walking past the living area you will find 2 comfortable queen beds as well as a closet to hang your clothes. Opposite the sleeping area is a full bathroom with a tub. At the end of the unit you will find a full kitchen with a refrigerator, stove, dishwasher, microwave, kettle, toaster, and coffee machine. In this space is also a dining table that seats 4.brbrGuest access:brGuests are free to use any space within their unit as well as any of the outdoor spaces which include the front patio or lawn.brbrOther things to note:brThis is an older building and there are tenants above the unit you will be staying in. The tenants are careful to avoid making any loud disturbing noise but if at any time it is too loud please message me and I will let them know immediately.

Relaxing Chicago Studio

Chicago, Illinois, United States

1

Bath

Sleeps

$233.16

Bring the whole family to this great place with lots of room for funbrComfortable 1100 sqftbr3 BR 1 BA located in the beautiful and hip Logan SquarebrLarge beds, couch, dining room with wifi/roku TVbrPatio for relaxing + Free Garage ParkingbrSleeps 9 comfortably - 3 queen beds, 1 large sleeper sofa, 1 air mattressbrShort drive from Logan Theater, multiple art galleries, multiples breweries and arcades, and the famous Milwaukee Avenue which is full of food, drinks, and art.

Jumbo 3bd In Hot Logan Square!

Chicago, Illinois, United States

Bed

Bath

Sleeps

$728.17

Escape to this cozy Chicago apartment, just steps from the city's vibrantbrbrdining scene and attractions. Enjoy the nearby Lakefront Trail, perfect forbrbrbiking or a peaceful walk with stunning views of Lake Michigan. After a day ofbrbrexploring, unwind in the apartment with a game of pool, dive into board games,brbror relax with a good book or magazine. The comfortable and welcoming space isbrbrideal for travelers looking for a mix of city adventure and relaxation.brbrbrbrWhether you're here to explore the city's rich culture or simply looking for abrbrcomfortable place to unwind, this apartment offers the best of both worlds.brbrWith easy access to restaurants, scenic bike trails, and plenty of indoorbrbrentertainment options, you'll have everything you need for an enjoyable staybrbrin Chicago. Book your perfect getaway today and make the most of your time inbrbrthe Windy City!brbrbrbr★☆ NEARBY ATTRACTIONS, LANDMARK & RESTAURANTS☆★brbrbrbr * Museum of Science and Industry (about 2.5 miles) - 11 min drivebrbr * University of Chicago - 6 min drivebrbr * Frederick C. Robie house - 12 min drivebrbr * Museum campus - Shedd Aquarium, Field museum, Alder Planetarium - 13 min drivebrbr * Navy Pier -17 min drivebrbr * McCormick Place - 9 min drivebrbr * Art Institute of Chicago - 15 min drivebrbrbrbr★☆ KEY FEATURES ☆★brbrbrbr * Pool tablebrbr * Reading Material ( books, magazines)brbr * Board Games brbr * Washer + dryerbrbrbrbr★☆ BEDROOM ARRANGEMENT☆★brbrbrbrBR1: 1 Queen Bed brbrBR2: 1 Queen Bed brbrBR3: 1 Queen Bed brbrBR4: 1 Queen Bed brbrThird Floor: Air Mattressbrbrbrbr★☆ LIVING ROOM ☆★brbrbrbrThe living room offers a cozy retreat with a TV, board games, a pool table,brbrand a selection of books, magazines, and reading materials.brbrbrbr★☆ KITCHEN & DINING ☆★brbrbrbrWhether you're whipping up a snack or a full meal, the fully equipped kitchenbrbrhas all the essentials. The open layout keeps you connected with guests in thebrbrliving and dining areas, and with plenty of seating and a cozy atmosphere,brbrit's perfect for family dinners or entertaining friends.brbrbrbr★☆ PARKING ☆★brbrbrbr * Free Street Parkingbrbrbrbr★☆ HOUSE RULES ☆★brbrbrbr * No smoking allowedbrbr * Pets are not permittedbrbr * Events, parties, and large gatherings are prohibitedbrbr * Loudspeakers with subwoofers are not allowedbrbr * Shoes must be removed before entering the unitbrbr * No eating or drinking on the pool tablebrbr * Furniture must not be rearrangedbrbr * Loitering in front of the building is not allowedbrbr * Please observe quiet hours from 10 PM to 7 AM.brbr * For safety, please make sure the main door and front gate are securely closed when entering and leaving the building.brbr * Please report any damages that occur during staybrbr * There is a $500 fee for smoking in the premises.brbr * Guests may request an early check-in (up to 3 hours before 4pm) or a late check-out (up to 2 hours after 10am), so long as there is not a reservation booked at our property for the day of your request. Please message us a day in advance to confirm availability and receive the applicable fee quote.brbr * Extra Guests: If more guests than permitted are found at the property, we reserve the right to deny entry based on policies. Extra guests will be treated as trespassers. An additional fee of $50/night per extra guest may apply, or we might request that you vacate the property.brbr * If uncertain about guest numbers or daytime visitors, please reach out. We aim to prevent any misunderstandings.brbrbrbr★☆ SECURITY CAMERAS ☆★brbrbrbrFor your safety and security, our property is equipped with exterior camerasbrbrlocated in the front communal lobby, monitoring the main entrance, and outsidebrbrfacing the street. brbrbrbrbrbr★☆ Book Now & Let Us Take Care Of You! ☆★brbrbrbrPlease note that this unit is part of a duplex. You will have the entire unitbrbrto yourself, but there is another unit that is part of the duplex that youbrbrwill not have access to.brbrbrbr

Condo

Spacious 4BR Condo | Pool Table | Near McCormick

Chicago, Illinois, United States

Bed

Bath

8

Sleeps

$503.54

Escape to this brand-new, stylish 3-bed, 2-bath Chicago apartment! Featuring a chic contemporary design with plush velvet sofas, it's perfect for work or leisure. Comfortably sleeps up to 6 guests. Located in a quiet, secure neighborhood just a short drive from Downtown Chicago and the United Center. Your ideal urban retreat awaits!brbrKey Features:br Bedrooms: 3 private bedrooms with one queen bed and three full beds.br Bathrooms: 2 full, modern bathrooms.br Living Area: Unwind with a large flat-screen TV and comfortable, stylish seating.br Kitchen: A clean, modern kitchen fully equipped with stainless steel appliances for all your cooking needs.brConvenience: In-unit laundry facilities are included for your use.brbrGuests will have full and private access to the entire 3-bedroom, 2-bathroom apartment. This includes all bedrooms, bathrooms, the living area, and the kitchen. You will not be sharing any part of the space with others.brbrWe believe in giving our guests space and privacy to enjoy their stay. We offer self-check-in for your convenience and will not be on the property during your visit. However, we are always available and just a message or phone call away if you need any assistance or local recommendations.

Modern 3BR Apt Near United Center

Chicago, Illinois, United States

Bed

Bath

Sleeps

$357.83

Newly remodeled , 20 min walk to the lake. 20 min drive from downtown and 25 min from airport. Second floor of two flat family owned and well maintained. Quiet place . Come and enjoy this beauty .Won't be disappointed.

Chicago charm! Quiet and inviting !

Chicago, Illinois, United States

Bed

Bath

Sleeps

$375.6

La Maison Verte is a Parisian-inspired 2nd floor walk up in a traditional Chicago 2 flat with vintage charm and modern amenities.brbrAs you step inside you’ll be whisked away to a traditional Parisian flat with 9 foot ceilings, loads of natural light, custom wood panel molding, ceiling medalians, white marble, and brass finishes. brbrThe French-inspired kitchen features blue cabinets and brand new Whirlpool appliances including gas range, ice maker, and stacked washer and dryer. Fully stocked with vintage glassware and dishes sourced from local antique shops. brbrSpacious 6 seat dining table with original built-in hutch which houses vintage barware and drink mixers. brbrThe master bedroom features an 1880’s French walnut Queen bed with a full length gold mirror and kidney shaped desk for any work from home needs.brbrThe home is a plant lovers dream with over 70 different plants sprinkled throughout. There is no better place for your morning coffee than the sun room/conservatory as you sit on a custom green velvet French Settee among the plants basking in the morning sun.

Private Vacation Home

Classic Chicago 2 Flat transformed into a Parisian plant lovers paradise

Chicago, Illinois, United States

Bed

1

Bath

Sleeps

$2169.82

Feel at Home, Unwind, and Enjoy the amenities you deserve at our Two 2-Story Downtown Penthouses (Combined Units) with Million $ ViewsbrbrGuests love staying with us because:br✅ Central location near Grant Park, Art Institute, & morebr✅ FAST WIFIbr✅ 2 parking passes in the attached garagebr✅ En-suite Laundrybr✅ KING bedsbr✅ Private Rooftop Deck w/ stunning viewsbr✅ Amenity Floor (Gym, Pool, Lounge, Doggy Park)br✅ 1 block from Red `L` subwaybr✅ Close to The Bean, Soldier Field, MuseumsbrbrThis is a combination listing:brR23000111258brR24000113941brbrThere isn`t another listing like this in Chicago - 2 Penthouses in the heart of Downtown with modern finishes and professionally designed decor.brbrBoth spaces are truly unique within Chicago`s Downtown `Loop` District. You will sit 28 floors up with expansive views throughout the home.brbrBoth units are a 2-floor penthouses.brbrOn the entry level floor are the two large bedrooms with KING beds and two bathrooms. The Master bedroom comes equipped with a walk-in closet. brbrThe 2nd level greets you with a modern kitchen, living area, and PRIVATE outdoor patio. brbrAlong with the units, you also have access to the amenity floor with lounge area, pool, gym, doggy care, and more!brbrYou have full access to the unit and the amenity floor, equipped with a pool, gym, lounge, and more!brbrWe`re here when you need us!brbrThe South Loop is such a dynamic mix of attractions and histories that the neighborhood tends to be seen as many different things to many different people. Consider the assorted areas that comprise the South Loop:brbrMuch of its eastern edge is encompassed by the Museum Campus, an impressive collection of cultural treasures that includes the Field Museum, Adler Planetarium and Shedd Aquarium. This campus sits on scenic lakefront parklands that are an extension of Grant Park. With 319 acres of green space and recreational fields, Grant Park is known as `Chicago`s front yard` to locals and also plays host to major city events such as Taste of Chicago, Chicago Blues Festival and Lollapalooza.brbrJutting out further into Lake Michigan is Northerly Island, a peninsula sought out by nature lovers, while along the southern edge the sports fans know Soldier Field as the stadium for the beloved Chicago Bears football team. Meeting attendees are most familiar with McCormick Place, the largest convention center in the country, which is also in the immediate area.brbrAnd yet there are even more facets to the South Loop. History buffs point out the Motor Row District along South Michigan Avenue and nearby Prairie Avenue District, the `Millionaire`s Row` that was lined with mansions belonging to Chicago`s most wealthy elite during the end of the 19th century.brbrIn the adjacent Printer`s Row neighborhood, urban loft condos now fill the commercial spaces in what was formerly the center of the Midwest`s publishing industry. Connections to this past are still seen within the venerable, independent book store and annual summer lit fest here. But business professionals and students have brought new life and redevelopment (though the vibe remains mellow), filling the restaurants, music clubs, smaller theaters and museums that have all established themselves in the community.brbrWe are very central and in close walking distance to the subway stops at Polk. We recommend NOT renting a car, and walking, ubering, and using public transit for your stay.brbrThe HVAC system is unique because it is a single duct system, meaning that it only blows heat or cool at a time - depending on the time of the year (set by City law). We provide fans and a floor HVAC unit within the property for the transition months.brbrThere is a NOISE MONITORING system within the home to track decibel noise level. Please respect our neighbors and do not get too loud outside quiet hours :)brbrRefund Processing PolicybrIn the event of a guest-initiated cancellation, any bank fees or payment processing charges incurred will be the responsibility of the guest and will be deducted from the refund amount.brbrRefundable Security Deposit: A $300 refundable security deposit is required and will be `held` or `authorized` (not `charged`) by Chicago Hospitality Club on your card. Any property damage or extra charges may be deducted from the deposit. VRBO collects platform payments/charges separately, while Chicago Hospitality Club handles the deposit, so seeing both on your statement is normal. The deposit is automatically released 3-7 days after checkout.br- No Local Guests (City or Suburbs)br- Quiet hours: 10pm to 8ambr- Minimum age of 30 to bookbrbr Last-Minute Bookings PolicybrTo ensure a smooth check-in, all same-day reservations will REQUIRE HOST APPROVAL. Please message us first so we can confirm and ensure everything is set for your arrival.brbrSmall Pet Fee (Under 20lbs, no shedding) - $300brLarge Pet Fee - (Over 20lbs) - $350 plus a $200 refundable security deposit and subject to host approval. brIf the pet sheds, we will require an additional $150 refundable Security deposit.brUnauthorized Pets - $250.00 plus any damages or additional cleaning costs incurredbrbrSmoking in Room/Common Area - $500.00 minimum charge and eviction from Rental UnitbrExcessive Cleaning - Up to $125.00 per hour of additional cleaning neededbrbrMandatory Mid-Stay CleaningbrStays of 14+ nights require a mandatory mid-stay cleaning, scheduled with the guest in advance. Additional cleaning fees apply.brDamaged or Missing Items - Varies depending on cost of itembrMissing Keys - $100.00 minimum chargebrMissing Fob - $500.00 minimum chargebrLost parking pass - $300.00brbrNoise Complaints: potential warning issued or, if necessary, eviction with no refund and a charge of up to $1,000.00brParty in Unit or Common Area - Up to $2,000.00 plus any damages to the unitbrForgotten Personal Belongings - $75 minimum charge for handling and shipping.brIf keys are left inside the home, and we come to give you re-entry it is $50.brUnauthorized Late Check Out -Up to the cost of any impacted nights subsequent to originally scheduled check-outbrbrNo Unauthorized Late Check Out without notice from Host.br-Early check-ins/Late check-outs can sometimes be accommodated by our cleaning service for $50 per hour fee (per unit)brbrAll guest names and ages must be registered before you are allowed to check-in.brbr brbrQ: Is the neighborhood safe brA: Very much so. 24 hours a day.brbrQ: Do I need to bring towels, a hair dryer, or linens brA: Nope! we provide all these things. We also provide you and your guests with a starter pack of toilet papersbrbrQ: When can I check in or check out brA: Check in is 4pm and check out is 10am. Early check ins can be difficult if there are guests who checked out same day. We ask for an early check-in, or a late-check out fee, if you request either.brbrQ: Is the Gym and Amenity floor shared brA: Yes, it is shared so please be respectful of other tenants and guests using the space.brbrQ: Luggage Drop-Off / Storage brA: If you do not have flights that coincide with our check-in and checkout times, you may store your bags with Radical Storage near our property. It allows you to store your bags for your optimal time :)brbrQ: Can I come and go as I please brA: Yes. And we wouldn`t trust any listing with which this isn`t the case.brbrQ: What about PARKING brA: Your reservation comes with two parking cards for the attached parking garage.brbrQ: Is the place professionally cleaned between guests brA: Yes, and we take pride in providing a clean home for guests.brbrQ: What`s my total booking price brA: We honestly don`t know. The total price, including fees, will appear after you enter your dates. Rates vary daily and are adjusted automatically by the platform`s pricing algorithm, so we don`t directly control them.brbrQ: Are the beds comfortable brA: Very. Some guests say they`re the best they`ve ever slept on!brbrNo Agency Relationship. Nothing herein contained shall be deemed to authorize or empower either party to act as agent for the other party to this Agreement, or to conduct business in the name, or for the account, of the other party to this Agreement.brbrGuest VerificationbrAs part of our vetting process, we may ask guests to confirm a few details — such as their names, ages, where they’re traveling from, or their travel plans — before accepting a booking. In some cases, we may also request a valid government-issued ID for verification purposes. This helps us ensure that all stays are safe, transparent, and in line with our house policies.brbrUnresponsive GuestbrIn some cases, if a guest does not respond within a reasonable period, we reserve the right to cancel the reservation. brFor same-day bookings, this timeframe is up to 2 hours or less. For all other bookings, this timeframe is up to 8 hours. This ensures that we can provide the best experience and availability for all our guests.brbrOnline Check-In & Rental Agreement RequiredbrBefore receiving check-in instructions, all primary guests must complete our online check-in form and review/sign our rental agreement. This helps verify guest details and ensures a smooth, secure arrival.brbrEXTRA GUEST CHARGEbrThe base price covers 10 guests. For more than 10 guests, there is an extra guest fee of $25 per guest for the full number of nights.brExample: 1 extra guest for a 5-night stay = $25 × 5 nights = $125.brbrKeys & AirTags:brFor transparency, some building keys or fobs may have an AirTag attached for loss prevention. The AirTag is only used to locate the key if it is lost and is never used to track guests or their movements. Guests are not required to carry the key at all times, but we recommend keeping the AirTag attached to help avoid replacement charges if the key is misplaced.brbrSecurity Deposit (Families with Young Children)brA security deposit may be required for groups traveling with two or more children under 14 years old, as a precaution against accidental damage and cleaning. The deposit is fully refundable, provided there is no damage to the property after a standard post-checkout inspection.

Downtown Penthouse 5bd VIEWS | Parking, Gym+Pool

Chicago, Illinois, United States

5

Bed

5

Bath

14

Sleeps

$297.23

Located in Chicago, this corporate apartment is a cool retreat for travelers. With two bedrooms, including one cozy queen bed, guests find plenty of space to relax. The pleasant bathroom features a refreshing shower and a handy hair dryer. Whether you’re winding down after a busy day or gearing up for a new adventure, this enchanting spot offers a comfortable stay. Book now and enjoy everything this corporate apartment has to offer.

Corporate apartment with 2 bedrooms and fantastic view of lake and skyline

Chicago, Illinois, United States

Bed

Bath

Sleeps

$281.41

Enjoy comfort and sustainability in this beautifully designed South Side retreat. Located in a modern, solar-powered green home, this space is perfect for guests looking for both relaxation and access to Chicago’s top attractions. Just minutes from Hyde Park, Jackson Park, the Obama Presidential Center, the University of Chicago, Museum of Science and Industry and Lake Michigan where you’re well-placed to explore both culture and nature.

NEW Eco Stay by UChicago, Lakefront & Hyde Park!

Chicago, Illinois, United States

Bed

Bath

Sleeps

$314.19

This is a beautiful apartment only a short walk away from Clark street which features amazing nightlife and some of the best cuisine Chicago has to offer. Additionally it is only a 20 minute drive or a quick train ride from downtown Chicago. This apartment is beautifully furnished and a perfect place to be your home away from home while you are traveling.

Blissful Chicago Getaway

Chicago, Illinois, United States

Bed

Bath

Sleeps

$158.35

Discover Chicago like a true local in this stylish 2-bedroom lower-level retreat. Perfect for small groups, this tranquil hideaway features a cozy queen bedroom, a twin daybed, and a comfy twin sofa bed in the living room—ideal for up to 4 guests. After a day of exploring the city, relax in the spacious living room or unwind with your favorite shows on the Smart. TV. With thoughtful amenities like high-speed WiFi, air conditioning, and a hair dryer, your stay is designed for comfort and ease. Welcome to your private Lower-Level Luxury Apartment, complete with its own separate entrance for privacy and convenience. Inside, you’ll find:br • ✨ A serene queen bedroom for restful nightsbr • A versatile twin daybed and additional twin sofa bed for flexible sleeping arrangementsbr • A fully equipped kitchenette, perfect for quick meals or late-night snacksbr • A modern living room with Smart TV and plenty of space to relaxbr • Easy, free street parking right outsidebrbrWhether you’re visiting for work, a weekend getaway, or an extended stay, this cozy spot offers both comfort and convenience. The entire apartment is yours to enjoy! Enter with ease using the Wi-Fi enabled smart lock for seamless self-check-in and check-out. You’ll have private access to all areas: bedrooms, bathroom, living room, kitchenette, and of course, unlimited high-speed Wi-Fi. Location and TransportationbrbrNestled between O'Hare International Airport and the bustling downtown of Chicago in a quiet and safe neighborhood, the apartment's location offers a quiet and peaceful home base for city exploration. With a self-check-in smart lock keypad and a separate entrance for the unit, your coming and going will be hassle-free. Free street parking is available, with no permit zone requirements. It’s always easy to find a parking spot.

Private Vacation Home

Lower level luxury

Chicago, Illinois, United States

Bed

Bath

Sleeps

$603.82

A refreshing, sophisticated oasis with added flare like vibrant, oversized works of Chicago memorabilia. Ideal for a family or group of friends, this suite sleeps 6 between 1 King Bedroom + 1 Queen Bedroom (+queen sleeper sofa) and 2 full bathrooms. A stocked kitchen is on hand to cook a meal (or simply request a chef, you’re on vacay after all) and serene bathrooms complete with luxury bath products feels like home. Yoga mats aid a good sweat while your own washer + dryer keep things fresh. Sleep6 brand mattresses and supple linens allow for an optimal night’s rest. A washer + dryer, Sonos, YouTubeTV, and fast Wi-Fi add to the ease and comfort.brAccess codes will be sent via text or email on the day of check-in. After booking, a registration form will also be sent and must be completed prior to arrival.brbrCheck-in time is 3:00 PM, and check-out time is 11:00 AM.brbrNo smoking inside the property.brNo parties allowed.brNo cats allowed.brQuiet hours start at 10:00 PM.brbrAccess codes will be sent via text or email on the day of check-in. After booking, a registration form will also be sent and must be completed prior to arrival.brbrCheck-in time is 3:00 PM, and check-out time is 11:00 AM.

Hotel

The Neighborhood Hotel - Lincoln Park 304 - Two Bedroom

Chicago, Illinois, United States

3

Bed

Bath

6

Sleeps

$172.88

A Comfortable Chicago Home Base — Pet-Friendly & Work-ReadybrbrWelcome to your Chicago home away from home, set in a quiet residential pocket on the city’s southwest side. This thoughtfully maintained house is designed for travelers who want a place that feels easy to live in—whether you’re here for work, family visits, or an extended stay.brbrInside, the home is clean, comfortable, and practical. The living spaces are relaxed and welcoming, with room to unwind after a long day. Bedrooms are quiet and well suited for restful nights, and the fully equipped kitchen makes it simple to keep your routine—morning coffee, home-cooked meals, or quick workday lunches.brbrWe are proudly pet-friendly, with a private yard that gives both you and your pup a little extra breathing room. It’s ideal for morning walks, quick outdoor breaks, or just letting your dog stretch out after a travel day.brbrFor business travelers and remote workers, this home checks the right boxes. There’s reliable Wi-Fi, comfortable spaces to set up a laptop, and a calm environment that makes it easy to focus during the day and fully unplug at night. Whether you’re working remotely, in town for a project, or traveling for business near Midway Airport, this home offers a more relaxed alternative to a hotel stay.brbrThe neighborhood itself is peaceful and residential, providing a welcome contrast to the pace of downtown—while still offering convenient access to Midway Airport, major highways, and public transportation. Getting into the city, to meetings, or out exploring Chicago is simple and stress-free.brbrIf you’re looking for a stay that’s comfortable, pet-friendly, and well-suited for work or longer visits, this home is an easy fit.

Private Vacation Home

2-bedroom house on a quiet, tree-lined street with modern amenities throughout

Chicago, Illinois, United States

Bed

Bath

Sleeps

$593.2

A refreshing, sophisticated oasis with added flare like vibrant, oversized works of Chicago memorabilia. Ideal for a family or group of friends, this suite sleeps 6 between 1 Queen Bedroom + 1 Bunk Bed Bedroom + Queen Sleeper & 2 full bathrooms. A stocked kitchen is on hand to cook a meal (or simply request a chef, you’re on vacay after all) and serene bathrooms complete with luxury bath products feels like home. Yoga mats aid a good sweat while your own washer + dryer keep things fresh. Sleep6 brand mattresses and supple linens allow for an optimal night’s rest. A washer + dryer, Sonos, YouTubeTV, and fast Wi-Fi add to the ease and comfort. Don't forget to enjoy your morning coffee outside with direct access to the courtyard!brAccess codes will be sent via text or email on the day of check-in. After booking, a registration form will also be sent and must be completed prior to arrival.brbrCheck-in time is 3:00 PM, and check-out time is 11:00 AM.brbrNo smoking inside the property.brNo parties allowed.brNo cats allowed.brQuiet hours start at 10:00 PM.brbrAccess codes will be sent via text or email on the day of check-in. After booking, a registration form will also be sent and must be completed prior to arrival.brbrCheck-in time is 3:00 PM, and check-out time is 11:00 AM.

Hotel

The Neighborhood Hotel - Lincoln Park 203 - Two Bedroom

Chicago, Illinois, United States

3

Bed