Vacation Condo Rentals By Owner In Chicago, IL

Steps from Wrigley Field, my 2 bed/2 bath + Den penthouse with a private rooftop is the perfect “home base” for your group. With the excitement of Wrigleyville in your backyard and the sights of downtown are a quick train ride away. brbrThis location is only two blocks from the Addison Red Line El stop which will take you to downtown Chicago in just 15-20 minutes! We are within walking distance of dozens of amazing restaurants, shopping, nightlife, public transit, and easy access to the lake with running trails and beaches. Wrigley Field is now a year round destination including not only major league baseball all summer long, but now is known as a world class music venue for top performers, a celebrated college football stadium and during the holidays, the Gallagher Way Park, located just outside the park, transforms to the Chriskindlmarket Wrigleyville! Enjoy holiday inspired food, drinks, shopping and a well lit, full service, ice skating rink!brDue to the condo’s location being 0.1 miles from Wrigley Field parking is limited. One parking spot is available with your booking. An additional parking spot can be purchased on a daily rate if reserved at least two weeks in advance. brbrThe spacebrThe main floor features an open floor plan that combines the kitchen with the main floor living space with an abundance of natural light. The main floor also has two bedrooms and two bathrooms. One bedroom has a king bed, and ensuite bathroom. The second bedroom has a queen bed. The top floor features a den with a queen bed.brLicense numberbrR22000088938

The Wrigleyville Penthouse with Private Rooftop!

Chicago, Illinois, United States

Bed

Bath

7

Sleeps

$97.12

2 bedroom 2 bath very cozy spacious in Southshore Chicago. brFully equipped kitchen, Dining room, work space, free WiFi, laundry in unit, free street parking.brAmenities includedbrBath: large and small towels, hair dryer, hand soaps, lotion, et,cbrLaundry in Unit:. Washer and dryer, detergents etcbrIroning board, iron, brKitchen Fully Equipped for making your own meals,. refrigerator, stove, microwave, disheasher coffee maker silverware, breakfast table brSpacious work Workwith chair, lounge chair.brliving room has vouch , chairs, dining table w chairs . Carpet throughout the apartment.brbrwalking distance from public transportation. a minute from Lakeshore drive. 20 minutes driving to downtown Chicago.brit's a very spacious beautiful place to stay. secured gated building. great for the traveling professional.brbr

Cozy Southshore Condo

Chicago, Illinois, United States

Bed

Bath

Sleeps

$430.66

Welcome to The Picasso on Lincoln Park. This is Chicago’s BEST location… steps away from Lincoln Park, North Avenue Beach, The Lincoln Park Zoo, the lively North & Wells restaurant/bar scene, Armitage shopping district, easy Ubers 5-minute rides to Wrigley Field, Navy Pier, The Loop downtown, The Art Institute and Museum Campus, River North restaurants, and Michigan Ave shopping. About the property… this place has style!!! Charming and elegantly decorated with an arthouse theme for those special getaway weekends. Recently rehabbed so everything feels brand new. The place is kept in immaculate condition… professionally managed, triple cleaned between guests, and personally checked on by the local owner who takes immense pride in creating a special experience for every guest. This property is in a historic landmark building… perfect for travelers who admire pristinely maintained old-school Chicago elegance. The unit is intimate and charming, about 500sq feet with a hotel-junior-suite feel, integrating a lofted bedroom that creates an elegant flow between rooms, on the 3rd floor (walkup). Modern amenities include Wifi, Netflix/Amazon/YouTubeTV access, Bluetooth stereo speakers in the bathroom and bedroom, laundry room in basement (coin operated), excellent heat and AC for your optimal comfort, free street parking in front of building or a paid parking lot 2 blocks away in Lincoln Park. Yours to enjoy for a special intimate Chicago experience!brbr*Note: the indoor fireplace is for decoration only and is not operational*

Chicago’s BEST location… Lincoln Park, Lake Michigan, Wrigley Field, and more!

Chicago, Illinois, United States

1

Bed

1

Bath

Sleeps

$181.94

Your Chicago adventure begins at this delightful 2-bedroom condo. With 3 queen beds and 2 bathrooms featuring a bathtub and shower, guests will feel right at home. The additional living room space offers 2 full beds for extra comfort. Enjoy your time in Chicago at our cozy condo.

Modern Comfort, Urban Charm

Chicago, Illinois, United States

Bed

Bath

10

Sleeps

$286.95

Welcome to your extended-stay retreat in the heart of Chicago’s South Loop. Whether you’re here for work, relocating to the city, enjoying a few months of travel, or in transition between homes, this beautifully furnished 2-bedroom, 2-bathroom high-rise residence offers all the comforts of home with the polish and amenities of a luxury hotel.brbrLocated on the 17th floor of a modern full-service building, this home offers spectacular views of Lake Michigan, Grant Park, and the Chicago skyline. The spacious layout, thoughtful furnishings, and quiet residential atmosphere make it ideal for longer stays—30 nights or more—with every detail designed to help you settle in with ease.brbrThis residence is perfectly suited for:brbr• Corporate professionals on 2-6 month+ assignmentsbr• Executives or graduate students seeking a refined, turnkey living spacebr• Families in between homes or relocating to the citybr• Guests displaced from their residence due to repairs or insurance eventsbr• Travelers seeking a longer, more comfortable stay near Chicago’s best attractionsbrbrTHE SPACEbrStep into a bright and airy living space, filled with natural light from floor-to-ceiling windows. The open layout offers flexibility and flow, while clean lines, modern furnishings, and neutral tones create a peaceful, inviting atmosphere. Unwind in the comfortable living area, prepare your favorite meals in the fully equipped kitchen, or enjoy a morning coffee on your private balcony overlooking the lake and city.brbrThe full-sized kitchen includes:brbr• Stainless steel appliancesbr• Granite countertopsbr• Oven, stovetop, microwave, dishwasher, and refrigeratorbr• Cookware, bakeware, dishware, glassware, utensils, and serving piecesbr• Blender, toaster, coffee maker, air fryer, rice cooker and tea kettlebr• Pantry space and kitchen island with seatingbr• Dining table that seats 6 comfortablybrbrBEDROOMS & BATHROOMSbrBoth bedrooms are designed as private suites—each with its own en-suite bathroom and dedicated work-from-home setup. This setup is perfect for couples, colleagues, or families who value privacy while sharing space.brbrEach bedroom includes:brbr• Queen-sized bed with high-quality linens and blackout curtainsbr• Spacious closet with hangers, drawers, and extra beddingbr• En-suite bathroom with full shower and/or tubbr• Premium towels, shampoo, conditioner, and body washbr• Desk, office chair, and task lightingbr• Smart TV with streaming capabilitiesbrbrBALCONY & VIEWSbrFrom the 17th floor, enjoy panoramic views from your private balcony. This east-facing terrace offers front-row seats to sunrise over Lake Michigan, the changing colors of Grant Park, and Chicago’s iconic skyline. It’s the perfect space to relax, journal, take calls, or simply enjoy a peaceful break from the day.brbrBUILDING AMENITIESbrThe building offers access to a curated list of amenities that make longer stays more comfortable and convenient.brbrIncluded building features:brbr• 24/7 door staff and secure entry with key fob accessbr• Outdoor lap pool and hot tubbr• Fully equipped fitness centerbr• Business center with Wi-Fi, printing, and quiet workspacesbr• Elevator access throughout the buildingbrbrPARKINGbrThe unit includes two heated, indoor garage parking spots—an extremely rare find in downtown Chicago. Whether you're commuting daily or just want the convenience of a secure, private parking space, your vehicle will stay protected and accessible year-round.brbrLOCATIONbrThis home is situated in the South Loop’s quiet, residential corridor—moments from some of Chicago’s most beloved landmarks. It’s walkable, scenic, and offers the perfect balance of peace and proximity.brbrWithin a 5–10 minute walk:brbr• Grant Parkbr• Lakefront trail (biking, jogging, strolling)br• Museum Campus: Field Museum, Shedd Aquarium, Adler Planetariumbr• Soldier Fieldbr• Columbia College and Roosevelt Universitybr• Multiple grocery options: Trader Joe’s, Mariano’s, Whole Foodsbr• Cafés, neighborhood bars, yoga studios, and local dining favoritesbrbrACCESS & TRANSPORTATIONbr• 3-minute walk to CTA Red, Green, and Orange linesbr• Direct bus routes to downtown, Hyde Park, and West Loopbr• Quick access to Lake Shore Drive, I-90/94, and I-55br• 20 minutes to Midway Airportbr• 35 minutes to O’Hare Airportbr• Minutes to McCormick Place and Loop office towersbrbrWHO THIS HOME IS PERFECT FORbrThis home is designed for guests who want more than a hotel—but expect the same level of ease and service. Whether you're on a temporary work assignment, settling into a new life in the city, or need a peaceful home base while yours is being restored, this space was made for extended comfort.brbrPerfect for:brbr• Corporate travelers (short-term assignments or consulting projects)br• Couples or colleagues sharing space with separate suitesbr• Families relocating or renovatingbr• Insurance housing guests needing quality, furnished living after a fire or floodbr• Snowbirds spending part of the year in Chicagobr• Medical or academic professionals on rotationbr• Digital nomads seeking a city stay with privacy, workspace, and location perksbrbrFAMILY-FRIENDLY FEATURESbrWe welcome guests with children and can provide the following upon request:brbr• Pack-and-play cribbr• High chairbr• Child-friendly utensils and platesbr• Safety gates or outlet covers (if needed)br• Nearby family-friendly attractions and parksbrbrREMOTE WORK READYbrThis unit is ideal for working from home. With two private workstations, fast internet, and building amenities designed for focus and flexibility, you can be productive while staying fully comfortable.brbrWork-from-home features include:brbr• Two separate desk areas with natural lightbr• Ergonomic seatingbr• High-speed Wi-Fi (400 Mbps)br• Business center with printers and private call spacesbr• Ample space for dual monitors or travel workstationsbrbrCONVENIENCES & EXTRASbr• In-unit washer and dryerbr• Smart TVs in living room and bedroomsbr• Central heat and air conditioningbr• Hair dryer, iron, ironing board, vacuumbr• Cleaning tools and supplies providedbr• Monthly cleaning and linen refresh available (for additional fee)brbrBOOKING INFORMATIONbr• Minimum 30-night stay (required by building rules)br• Signed rental agreement and photo ID requiredbr• All guests must be registered prior to check-inbr• Check-in: 3:00 PM | Check-out: 10:00 AMbr• Early check-in or late check-out available on request (subject to availability and fee)brbrABOUT YOUR HOSTbrWe are full-time hospitality professionals and local hosts committed to providing elevated, personalized care. From your first inquiry through the end of your stay, we’re here to make sure you feel truly at home.brbrWhether you’re in town for business, in transition, or simply taking time to slow down and enjoy the city, we’re happy to accommodate your unique needs. We pride ourselves on responsiveness, clarity, and creating a space that feels as relaxing and effortless as possible.brbrQUESTIONS OR CORPORATE REQUESTS brIf you're a relocation specialist, HR manager, or insurance housing coordinator looking for high-quality, fully furnished accommodations for your client or employee, we’d be happy to partner with you. We have experience working with corporate mobility programs, direct billing arrangements, and ALE housing placements through major providers. Whether you're managing a temporary work assignment, medical rotation, family relocation, or a household displacement due to fire or flood, we’re committed to providing a smooth, professional experience for both you and your client.brbrLet us know your program requirements, preferred arrival dates, and any custom needs—our goal is to make every extended stay feel effortless, elevated, and turnkey from day one.brbrWe look forward to supporting your placement.

Suite Success • Business Class Living • Sleeps 4

Chicago, Illinois, United States

Bed

Bath

4

Sleeps

$374.78

Experience Elevated Urban Luxury in Chicago’s South Loop:brWelcome to your home away from home—a sprawling, sun-drenched 3-bedroom, 3-bathroom high-rise sanctuary perched on the 14th floor of one of downtown Chicago’s most desirable residential buildings. This fully furnished residence offers over 1,800 square feet of upscale comfort, panoramic views, and hotel-style amenities. Whether you're in town for business, relocation, extended medical care, or simply to enjoy Chicago, this space provides the perfect blend of style and convenience.brbrWith modern finishes, floor-to-ceiling windows, and breathtaking views of Grant Park and Lake Michigan, this home combines the comfort of a thoughtfully designed residence with the sophistication of a luxury hotel. Ideal for traveling professionals, digital nomads, families, and long-term vacationers, it’s your gateway to the best of Chicago—day or night, work or play.brbrSpacious Layout & Premium Design Features:br• 3 generously sized bedrooms, each with its own ensuite full bathroombr• High ceilings, oversized windows, and Lake Michigan + Grant Park viewsbr• Fully furnished with designer pieces and premium beddingbr• Smart TVs in every room with streaming services preloadedbr• High-speed Wi-Fi throughoutbr• 2 dedicated work-from-home desks with ergonomic chairs and excellent lightingbrbrEach bedroom offers hotel-quality privacy, blackout curtains, and ample closet space—perfect for coworkers traveling together, couples sharing a space, or families needing room to spread out and recharge.brbrChef’s Kitchen & Dining for Eight-brThe open-concept kitchen is fully equipped and perfect for everything from a quick breakfast to a full dinner party.brbr• Stainless steel appliances including French-door refrigerator, oven, stove, microwave, and dishwasherbr• Dishes, utensils, cookware, cutting boards, and knife sets all providedbr• Coffee maker, toaster, blender, and morebr• Large island with bar seating for 4br• Dining table with seating for 6–8brbrWhether you're cooking for the family or bringing in takeout from a Michelin-starred restaurant, you’ll find everything you need to enjoy meals in.brbrRelax in Comfort & Style - brbrThe inviting living room features:br• Plush sectional sofabr• Large smart TV with surround soundbr• Floor-to-ceiling windows with iconic city and lake viewsbr• Private balcony with patio seating, ideal for coffee at sunrise or cocktails at sunsetbrbrEveryday Essentials, Thoughtfully Includedbrbr• In-unit washer and dryer – No shared laundry rooms herebr• Two heated garage parking spaces – A rare perk in downtown Chicagobr• Climate control in each room – Stay comfortable year-roundbr• Secure key fob entry and 24/7 doorman servicebrbrWorld-Class Building Amenities -brbrEnjoy the full spectrum of luxury building perks without ever leaving home:br• Indoor heated pool & spabr• Fully equipped fitness center with cardio and weightsbr• Game room with pool table and lounge seatingbr• Business center and conference room for remote work or meetingsbr• Outdoor grill terrace with tables and lounge chairsbr• Spacious community lounge perfect for informal gatheringsbr• 24/7 doorman, package room, and optional dry-cleaning pickup/drop-offbrbrUnbeatable Location in Chicago’s South Loop - brbrJust outside your front door is the best of Chicago:br• Grant Park – Your front yard, with gardens, fountains, and festivalsbr• Museum Campus – Field Museum, Shedd Aquarium, and Adler Planetarium within walking distancebr• 12th Street Beach & Lakefront Trail – Jog, bike, or relax by the lakebr• Soldier Field – A short stroll to concerts and Bears gamesbr• Downtown Chicago – Less than 10 minutes by car or bikebr• McCormick Place, Loop offices, and local hospitals – All easily accessiblebr• Public Transit – CTA Red, Green, and Orange lines nearby; Divvy bikes one block awaybr• Groceries & Essentials – Trader Joe’s, Mariano’s, Target, and Walgreens within minutesbrbrVibrant Dining, Shopping & Entertainment - brbrExplore the South Loop’s rich variety of walkable options:br• Casual Cafes – Overflow, Dollop, and Hero Coffeebr• Upscale Dining – Acadia, The Chicago Firehouse, and Socialebr• Family Favorites – Eleven City Diner, Yolk, and Burger Barbr• Bars & Lounges – VU Rooftop Bar, Tapster, and First Draftbr• Retail & Convenience – Roosevelt Collection shops, H&M, movie theater, and morebrbrFamily-Friendly and Perfect for Leisure Travel - brbrThis home is not just for business travelers—it’s a fantastic base for families exploring Chicago. From nearby playgrounds and beaches to hands-on museum exhibits and parks, everything is accessible without the need for a car.br• Pack-n-play and high chair available upon requestbr• Quiet and secure building with elevator access and family-safe amenitiesbr• Plenty of space for parents to work while children nap or playbr• Easy access to Navy Pier, Maggie Daley Park, and the Children’s MuseumbrbrWhether you're in town for summer break, a sabbatical, or a long family vacation, this property provides the comfort, location, and flexibility families need—without compromising on style.brbr30+ Day Stays Only – Ideal for Long-Term Guests - brbrThis home is available exclusively for 30-night minimum stays. It’s an ideal fit for:br• Corporate Relocation & Executive Staysbr• Medical Travel for Nearby Hospitalsbr• Insurance Housing for Families Displaced from Homebr• Digital Nomads Looking for a Luxury Chicago Viewbr• Visiting Professors, Musicians, Athletes, and Entertainers in Residencybr• Families in Between Homes or Renovating NearbybrbrWhat Guests Love Most:br✓ Iconic views of Lake Michigan and Grant Parkbr✓ Spacious layout with full privacy in each bedroombr✓ Two WFH setups for remote professionalsbr✓ True luxury living with hotel-style building amenitiesbr✓ Walkable to top cultural attractions and restaurantsbr✓ Safe, quiet, and professionally managedbrbrBook with Confidence:brOur home is professionally cleaned and maintained to the highest standards. You’ll enjoy full access to building amenities, a dedicated host team for support, and thoughtful extras designed to make your stay seamless.brbrWhether you're here for a month, a season, or longer, you'll find this residence offers everything you need for a comfortable, inspiring, and luxurious Chicago lifestylebr

Penthouse Paradise •Executive Elegance • Elevated Amenities • Sleeps 6

Chicago, Illinois, United States

Bed

Bath

Sleeps

$1356.77

Luxurious Upscale Duplex Penthouse Property - Sleeps up to 14 people with over 5600 sq ft in this Duplex Penthouse! Recently rehabbed with interior design updates to truly meet your needs and provide an unbelievable getaway in Chicago.brbrLocated in the heart of the city in the bustling River West Neighborhood! This Penthouse features 5 bedrooms, 2.5 baths with elevator and will accommodate all of your needs during your stay in Amazing Chicago! brbrSteps away from the CTA blue line and Expressway, you are close to the best Dining, Shopping, and Attractions the city of Chicago has to offer including the River North, West Loop, and Fulton Market! Grocery store, coffee shops, and fantastic restaurants within walking distance! This penthouse features 4 Queen Beds, 2 Twin beds, 1 daybed, 2 large couches, 3 Large Flat screens, and a massive kitchen with all top of line appliances! brbrAdditional sleeping arrangements with air mattresses can be arranged for when asked in advance. There are 2 large Living areas, washer/dryer, and a Game Room with poker table, shuffel board table, foosball, and state of the art Sonos entertainment system for your enjoyment! Luxurious master bathroom with a rain shower and Jacuzzi! brbrRooftop access with beautiful view of the Chicago skyline!! One garage spot available if arranged for in advance along with plenty of street parking available! These amenities must be requested ahead of time and subjected to a fee.brbrPerfect spot for any large gatherings including family/friend reunions, bachelor/bachelorette parties, corporate meetings, social events, holiday fun, and much more!brbrAdditional sleeping arrangements can be accommodated as there are three queen sized air mattresses!

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago, Illinois, United States

5

Bed

Bath

20

Sleeps

$607.7

Wrigleyville condo is located 1/2 block from Wrigley Field and Clark Street. Also close to Southport corridor and Brown Line. Easy access to Red Line which will take you downtown, Millenium Park, Grant Part, Maggie Daley, Hancock and Willis Towers. If you are interested in spending time on Lake Michigan, the lake is 3/4 mile where you can enjoy the trails by foot or by bike. brbrDue to COVID, we took some time off from renting our space, but are excited for others to enjoy Wrigleyville again as much as we do!! brbrCondo includes three bedrooms and three full bathrooms. Master bedroom is located on the main level, and includes a king size bed and a jacuzzi tub with shower. brbrGuest bedroom 1 includes a queen size bed and is also located on the main floor. It’s associated bathroom includes a steam shower. brbrGuest bedroom 2 is located in the lower level, includes a queen size bed in addition to a trundle bed. This bedroom can sleep 4 comfortably, a great room for kids! The bathroom has recently been remodeled and includes a large shower (as pictured). brbrMain level includes a living room/full kitchen supplied with all necessities to cook a full meal…..plates, basic utensils, coffee maker, etc. brbrLower level also includes living area with a sofa sleeper and a basic kitchenette. It does not have a stove or oven, but is set up similar to a hotel room with a fridge, microwave, toaster and coffee pot. brbrCondo is equipped with 4 TVs and set up for live streaming. Free wifi and printer available for all your business needs. brbrParking passes for neighborhood parking, one pass per day.

Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

Chicago, Illinois, United States

Bed

Bath

Sleeps

$598.2

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park!brbrMost homes don’t provide professional service along with “local vibes.” Guests love staying with us because:br-Central Location near public transit (no car needed!)br-FAST WIFIbr-On-floor free laundrybr-Lake & Park are 1 1/2 blocks awaybr-Comfy Queen bedsbr-Gymbr-3 blocks from Red `L` subwaybr-Close to Grant Park, The Bean, Soldier Field, MuseumsbrbrIf you`re interested in booking, see our FAQs below.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 at Grant Park.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.brbrWorking, relaxing, living. Our spaces have all the other essentials you need for your stay. brbr- Front desk check-inbr- Super-fast WiFibr- Fresh towels and bathroom essentialsbr- Pre-cleaning before your arrivalbr- Fitness centerbr- On-floor free laundrybr- Fully equipped kitchenbrbrPlease note that the building is shared with a college so you may see some college kids, but our floor secured and leased by us.brbrOnce you get inside the building, you walk to the secure elevators to go up to your floor.brbrOnce to the floor, you walk to your apartment. Once in the apartment, you will find a modern space with two bedrooms, one bathroom, a modern kitchen, and a living room equipped with Smart TV.brbrYou have private, full access to the unit, the shared gym, and the basketball court.brbrWe`re here to help but give you space to enjoy!brbrGuests are not allowed to check-in or be sent check-in information without providing: 1) Names 2) Ages 3) Emails and 4) Phone because they need to be sent to the front desk security.brbrNo Local Guests (City or Suburbs)brQuiet hours: 10pm to 8ambrMinimum age of 25 to bookbrbrLast-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 3 guests only. There will be an extra guest fee of $15 per guest per night if your group exceeds to 3 people.brbrNO PETS allowed. We`re sorry.brbrNo Animal PolicybrPlease note that the building has strict no-animal policies in place, which include service animals and emotional support animals. These restrictions are managed by building management and apply to all residents and guests for health and safety reasons.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 :)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 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: We 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 blocks.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 3 guests. For more than 3 guests, there is an extra guest fee of $15 per guest for the full number of nights.brExample: 1 extra guest for a 5-night stay = $15 × 5 nights = $75.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.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.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. The deposit is fully refundable, provided there is no damage to the property after a standard post-checkout inspection.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.brbrNo Local Guests (City or Suburbs)brQuiet hours: 10pm to 8ambrMinimum age of 25 to bookbrbrLast-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.brbr -Up to the cost of any impacted nights subsequent to originally scheduled check-outbr / - $500.00 minimum charge and eviction from Rental Unitbr - Up to $125.00 per hour of additional cleaning neededbr - Varies depending on cost of itembrbr : potential warning issued or, if necessary, eviction with no refund and a charge of up to $1,000.00br - Up to $2,000.00br - $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.br - $50.00 minimum chargebr - $150.00 minimum chargebrNo 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.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 :)brbrAll guest names and ages must be registered before you are allowed to check in.

Downtown 2bd #4 - Near Grant Park, Museums, Lake

Chicago, Illinois, United States

Bed

Bath

Sleeps

$361.44

Artistic, Foodie, Cultured, Luxuriant, Adventurer!!!!brIf any of these describes you….then Plzn Luxury Apartments is for you. The neighborhood is growing, diverse, safe with lots of shops and restaurants to choose.brThe spacebrNEWLY CONSTRUCTED modern Apartment in the vibrant and cultured PILSEN neighborhood!!!!brbrEnjoy walking the streets appreciating the murals while sipping on a choco-expresso from Café Jumping Bean or every 2nd Friday visit all the art studios for their events with your glass of wine literally a block away and visit the National Museum of Mexican Arts.brbrSavor the many taquerias or enjoy a drink in the many bars like Simones, La Vaca, Punch House or the Penny Whistle Bar and many many more.brbrPerhaps you might better enjoy a nice Sunday brunch at Duseks, Frida Room or delicious Monterrey style cooking at Canton Regio.brbrCheck out a concert or show at Thalia Hall, listen to live music at Honky Tonk Barbecue or sing your heart out at karaoke bars like Caminos De Michoacan.brbrPilsen is the neighborhood in the south side where the downtowners, suburbanites and north-siders come to enjoy art, food, entertainment and the night life and many of the food, music and art festivals!brGuest accessbrThe building is safe and secure with video surveillance and access code and intercom system to building and unit. Also, elevator accessible.brbrPilsen is neighborhood you want to explore on your feet....safe and walk-able!brbrThe apartment is located walking distance to major CTA Bus routes, Pink/Orange CTA train station and Metra/BNSF transportation.brbrClose to Illinois Medical District, UIC University, Greek Town, Little Italy, China town and downtown. Less than 1 mile from I-55, I-290 and I-90/94 express ways. Or Devy bike or scooter is always a few steps away!brbr1 dedicated garage parking space available plus plenty of street parking outside the apartment located on Cullerton St.brLicense numberbrR22000078828

Luxuriant, Foodie, Culture,

Chicago, Illinois, United States

Bed

Bath

Sleeps

$1026.5

This brand new home located in Wicker Park offers 7 beds, 6 baths, 2 living areas, 2 chef's kitchen and a dedicated dining area! brbrThis property is very unique as it is two units combined into one, allowing you to take advantage of 7 Bedrooms w/ 9 Beds (5 Queens, 2 Twin XLs & 2 Twins), 6 Bathrooms, 2 living spaces and 2 full kitchens.brbrWe are affiliated with Wave Sushi and offers eligible parties of 6 or more a free bottle of champagne/sake, just show your confirmed reservation! In addition to Wave Sushi the property is in a wonderful location close to bars, restaurants, coffee shops and public transit- the Blue Line is a 2 min walk. Hop on the blue line and come directly from O’hare airport and it is only a 10 min Uber/Lyft to the heart of downtown.brbrParking: There are 2 dedicated parking spots for guests, see the pictures for more details. Should you need additional parking there is typically free street parking in the area. Alternatively you can park in the garage located 1911 N. Western Ave, Chicago IL which is less than 400 feet from the property. They charge about $15 a day.brbrbr

The Exclusive- 7 Bed, 6 Bath Retreat

Chicago, Illinois, United States

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Bath

Sleeps

$1634.92

Immerse yourself in comfort with our 3600 sqft unit, featuring a 1400 sqft balcony and stunning city panoramas. This space includes three bedrooms, two rooms with two queen beds, one room with queen sofa bed and two full bathrooms. Enjoy a renovated entertainment center, and Outdoor speakers throughout. Ideal for groups, weekend getaways, or extended stays. No smoking indoors, smoking outside is allowed.br*Yacht/Boat Rentals are also available! brNote: Additional charges for events.

Downtown Penthouse Huge Patio with Great View

Chicago, Illinois, United States

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Bath

10

Sleeps

$298.8

This 4-bedroom condo is perfect for your escape to Wrigleyville in Chicago. The lovely space features a king bed, two queen beds, a bunk bed and a twin bed plus a two cozy living rooms. Guests enjoy three bathrooms, including one with a jetted bathtub for ultimate relaxation. The condo stays comfortable year-round with heating and air conditioning. Whether you’re unwinding after a day of exploring or gathering for a meal, this serene retreat offers plenty of room to spread out and recharge. Experience the magic of Chicago at our amazing condo.

Calling all Cubs Fans: Beautiful 4-bedroom condo across from Wrigley Field

Chicago, Illinois, United States

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Bath

Sleeps

$591.04

Welcome to our stylish 3-bed, 2-bath Condo in the heart of Chicago's vibrant West Town. Designed for your comfort, it's a perfect base to explore all Chicago has to offer.brbrYou're close to everything; walk to local eateries, or sip coffee at charming cafes. Wicker Park and West Loop are just a stone's throw away, offering a plethora of entertainment options.brbrThe Iconic attractions of Downtown Chicago are easily accessible, putting you close to Millennium Park, Magnificent Mile, and Navy Pier.brbrThis cozy condo makes the perfect home base for exploring Chicago, whether you're checking out the downtown attractions like the Bean or visiting one of the many vibrant neighborhoods outside of downtown. brbrCome explore all of the winter activities available in Chicago! Christkindlmarket! Jack’s Winter Pop Up! Multiple outdoor skating rinks! Winter Themed pop up bars scattered through the city!brbrAround the Neighborhood: brbrCoffee: br-Standing Passengers: 0.2 mi walkbr *Play old school video games over a latte*br-West Town Bakery: 0.7 milesbr-Prequel Cafe: 0.8 mi walkbr-Big Shoulders Coffee: 0.6 milesbr*If coffee at home is more your speed, the condo has a Keurig with K-Cup pods and creamer included during your stay. brbrBreweries/Foodbr-Forbidden Root: 0.5 mi walkbr-Irish Nobleman: 0.2 mi walkbr-Fry The Coop: 0.2 mi walkbr-On Tour Brewing Company: 0.6 milesbr-District Brew Yards: 0.5 milesbr-Goose Island Taproom: 0.9 milesbrbrWalk Score: 94brBike Score: 97 Looking for something different to do in Chicago Check out the WNDR museum tor the different Zoo Lights available all winter! Check out the Shedd Aquarium downtown!brbrCatching a game or concert ! Catch the Chicago Blackhawks and Chicago Bulls at the United Center! Only a short Uber ride from the condo.

3BD West Town Gem: Explore the Windy City in Style

Chicago, Illinois, United States

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Bath

Sleeps

$590.51

Beautiful Condo Quality Fully Furnished and Renovated space for monthly rental. brbrA super spacious 3 bedroom, 2 bath apartment that can accommodate everyone. The perfect combination of modern upgrades yet preserving the units historic and vintage charm. High ceilings and tons of windows that let in an amazing amount of natural sunlight.brbrStunning kitchen equipped with Granite Countertops, Stainless Steel Appliances, Dishwasher, Microwave, and Ice Maker.brbrBeautiful large double vanity bathrooms with walk-in shower. All bedrooms have great closet space. In-Unit laundry, Central AC/Heat. Outdoor space that is perfect for grilling, lounging, and entertaining guests.brbrThis property is nestled in one of the best pockets of Bucktown! Metra Clybourn Stop and Kennedy/I90 expressway are only 2 blocks away. The 606 trail, Bucktown Pub, Lotties, Mable's Table, Target, Costco, Mariano's, Mid-Town Athletic Club, Damen & Wicker Park Entertainment District, and much more are all located outside your door.brbrFree easy street parking, no permit required. Possible garage spot available. We are a non-smoking building. A wonderful apartment that is situated in a small, private, and intimate building.brbrWe are not a rental agency or a management company. We are the owners. This listing is for a long-term rental of this property. Our short-term listing and reviews can be found here: AirBNB.com/rooms/20026411.

Sunny & Spacious Bucktown 3Bd/2Ba w/Laundry

Chicago, Illinois, United States

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Bath

Sleeps

$268.16

Welcome to Your Stylish Home Base in Pilsen:brModern 3BR/2BA condo located in the vibrant East Pilsen/University Village neighborhood—perfect for corporate travelers, mid-term guests, and families alike. Comfort meets style with upscale finishes, spa-inspired amenities, and thoughtfully designed workspaces. Whether you're here for business, medical rotations, or just a change of scenery, you'll feel right at home.brbrThe Space:brThis spacious condo features three large bedrooms with cozy bedding, generous closet space (including a walk-in in the primary suite), and smart TVs throughout. The fully equipped chef’s kitchen boasts granite countertops, stainless steel appliances, and all the cookware essentials for your inner foodie.brbrThe primary bathroom offers a spa-like escape with a rainfall shower and modern finishes, while multiple WFH-friendly nooks and blazing-fast Wi-Fi ensure productivity and comfort during your stay.brbrWhat You'll Love:br✓ Spa-style primary bath with rainfall showerbr✓ Fully stocked chef’s kitchen with granite countersbr✓ Multiple dedicated work-from-home spacesbr✓ High-speed Wi-Fi & Smart TVs in every roombr✓ Garage parking with a 240V EV chargerbr✓ Pet-friendly for your furry family membersbr✓ Digital guidebook for a seamless experiencebrbrLocation, Location, Location:brNestled in Chicago’s cultural and culinary hub, you’re steps from:br• University of Illinois at Chicago (UIC)br• Rush, UI Health, and other major medical campusesbr• Pilsen’s top restaurants, coffee shops, and art galleriesbr• Public transit lines for easy access to the entire citybrbrJust minutes away from West Loop, Chinatown, downtown, McCormick Place, and Lake Michigan’s scenic trail. A perfect balance of accessibility and local charm.brbrGood to Know:br• Pet-friendly – just let us know in advancebr• Professionally cleaned and fully stocked before arrivalbr• Extended stays welcomebr• Please follow all house rules for a smooth experience

Suite Dreams • Designer Style • Central • Sleeps 6

Chicago, Illinois, United States

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Bath

Sleeps

$222.78

Welcome to our spacious and stylish 3-bedroom, 3-bath condo located in the vibrant, historic Bronzeville community of Chicago. Nestled close to the University of Chicago, the Harold Washington Cultural Center, and the iconic DuSable Museum, our condo offers a unique blend of modern comfort and artistic charm.brbrCondo Highlights:br- Each room boasts captivating wall art, adding character to your stay.br- Unwind in the master bathroom's jacuzzi tub, perfect for relaxation.br- Accommodates up to 5 guests comfortably, making it ideal for families, couples, friends, or students from nearby universities seeking furnished apartments.br- Proximity to transportation is a breeze, with CTA Greenline stops within walking distance and easy access to the Dan Ryan Expressway and Lake Shore Drive.brbrSpecial Experiences: We're here to make your stay memorable. If you're interested in guided tours or personalized services, please don't hesitate to ask. We're happy to assist with making your stay truly special.brbrNeighborhood Highlights:br- Explore the brand-new Bronzeville Winery and savor the local flavors.br- Discover the historic Washington Park, just a stone's throw away.br- Embrace the cultural richness of the DuSable Museum and the vibrant atmosphere of the Harold Washington Cultural Center.br- Sports enthusiasts will appreciate the proximity to White Sox Park.brbrHouse Rules:br- No Smoking: Smoking is not allowed inside the condo. Please use designated outdoor smoking areas.br- Respect Quiet Hours: Be mindful of neighbors and maintain quiet hours from 10 PM to 8 AM.br- No Parties or Events: Parties and large gatherings are not permitted.br- Pets: Unfortunately, we cannot accommodate pets.br- Cleanliness: Kindly leave the condo in the same clean and tidy condition as you found it.br- Security: Ensure all doors and windows are locked when you leave the condo.br- Guest Count: Please inform us of the total number of guests in your reservation to ensure a comfortable stay.br- Check-Out: Check-out time is at 11 AM, allowing us time to prepare for the next guests.brbrWe hope you enjoy your stay in our spacious, inspiring, and accessible Bronzeville condo. Feel free to reach out if you have any questions or special requests. We look forward to hosting you!br

Modern 3-Bedroom Condo with Artistic Flair in Historic Bronzeville

Chicago, Illinois, United States

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Bath

Sleeps

Select Dates for Price

Spacious, open air design in Rogers Park with 2 bedrooms and open kitchen dinning area. Living room and front sunroom are offer warm sunlight with breakfast nook and gas fireplace to relax in.brbrBest of both worlds location: Quiet residential block just a block away from restaurants and stores on Clark St. and Loyola, Lake Michigan, and Little India within a mile radius. Great playground nearby and 20+ restaurants within 5 block radius.brbrWe have great ratings on another rental platform over several years with this place, but are transitioning to VRBO because they have better customer service. (So we have no ratings yet on VRBO). For more reviews look on another common platform for a listing with title: Spacious Renovated Brownstone. Our prices are less on VRBO because we are transitioning and have no ratings here yet.

First Floor Brownstone Newly Renovated

Chicago, Illinois, United States

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Bath

Sleeps

$557.94

Summary:brbrEnjoy this beautiful space, just minutes away from the very best Chicago has to offer! This condo is walking distance from the bars, restaurants and Wrigley Field. Location is perfect for anyone looking to visit the city with easy access to parking and the red line train.brbrbrbrThe Space:brbrBright open space with free parking.brbrbrbrGuest Access:brbrGuests have access to the whole space.brbrbrbrThe Neighborhood:brbrThis condo is located in Lakeview, a neighborhood in Chicago. Navy Pier and Michigan Avenue are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Millennium Park and Grant Park. Looking to enjoy an event or a game See what's going on at Wrigley Field or United Center.brbrbrbrWhat's nearbybrbrbrbrWrigley Field - 3 min walkbrbrLincoln Park Zoo - 4 min drivebrbrNavy Pier - 9 min drivebrbrSoldier Field - 10 min drivebrbrMcCormick Place - 10 min drivebrbrbrbrGetting aroundbrbrbrbrAddison Station (Red Line) - 2 min walkbrbrChicago Ravenswood Station - 4 min drivebrbrChicago Midway Airport (MDW) - 39 min drivebrbrbrbrRestaurantsbrbrbrbrCorridor Brewery & Provisions - 14 min walkbrbrSushi + Rotary Sushi Bar - 15 min walkbrbrSouthport Grocery and Cafe - 13 min walkbrbrCoda Di Volpe - 15 min walkbrbrCheesie's Pub & Grub - Lakeview - 9 min walkbrbrbrbrGetting Around:brbrMany restaurants, bars and attractions are walking distance. You can also take the Red line to get downtown quickly.brbrbrbrOther Things to Note:brbrThis condo has potential for noise as it is centrally located in the city and next to the red line. The condo association has cameras outside that are constantly recording.brbrbrbr- Ring Camera at the front door. Records audio and video.brbrbrbrInteraction with Guests:brbrI can be available to message through the AirBnB Application.

Foosball, Steps from Wrigley, Private Parking

Chicago, Illinois, United States

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