Vacation Home Rentals By Owner In Chicago, IL

1700 sqft penthouse in the historic west end of the West Loop. Nestled on a quiet street, minutes away from incredible restaurants, coffee shops, yoga studios, and nightlife. A floor to ceiling gut-rehab was completed in 2019—the space was engineered with hospitality in mind. Featuring large bedrooms, loads of natural sunlight, an outdoor balcony, charging and hydration stations, a pellet grill, and smart home technology. We've done our part to ensure that you will enjoy your trip to Chicago.brbrWant advice Looking for that local knowledge We've got a digital guidebook telling you all the secrets! We're from Chicago. We live here. We want to make sure you have an amazing time in our beloved city!brbrMASTER BEDROOMbr- One queen bedbr- Dresser and mirrorbr(En suite bath)brbrSECOND BEDROOMbr- One queen bedbr- Walk-in closetbrbrTHIRD BEDROOMbr-Two Twin Size Bedsbr-Walk-in closetbrbrLIVING ROOMbr- One Sofabr-One Walter E. Smithe sleeper reclinerbr- 82in TV w/ Apple TV (HBOMax, Watch ESPN, Starz, and Showtime)br- Air Mattressbr-Hydration StationbrbrKITCHENbr- New stainless steel appliancesbr- Quartz counter tops and full tile back splashesbr- Island counterbr-Keurig (stocked with coffee and tea)br- Bar stool seatingbr- Pots and pans, tableware, glassware and silverware provided.brbrEN-SUITE MASTER BATHROOM (FULL)br- Oversized corner glass showerbr- Private in-bedroom entrancebr- Double sink quartz vanitybr- Jacuzzi tubbrbrDETACHED FULL GUEST BATHROOMbr- Recently Renovatedbr-Subway tilebr- Waterfall showerbr- Quartz vanitybr- Towels, body wash, shampoo, hair dryer, hand soap, and toilet paper provided in both bathrooms!brPRIVATE BALCONY, with seating and Camp Chef pellet grill. Pellet Grill is easy to use, pellets are stored on-site, giving you the opportunity to grill out during your entire stay.brbrFINISHESbr- Oak plank floorsbr- High-end lighting fixturesbr- Nest Thermostatbr- USB charging stationbr- In-unit washer dryerbr- Wi-Fi throughoutbr- Linens provided! Large closets with hangers, plus iron and board!brbr----------brPARKINGbrThere’s free street parking passes that will be on-site for guests throughout the duration of your stay. We will need to know the number of vehicles to ensure that we have enough parking passes available. One private parking space is available in the back of the building upon request and approval.brbr----------brCHECK-IN TIMEbrTypically, guests may receive the keys and drop their bags in the condo as early as 1pm. The cleaners do need until 3PM to do their work.brIf you'd like to drop your bags early, we can usually accommodate you.brbrIf you'd like to take a nap or shower right away, and the night before your stay isn't booked yet, let's discuss early check-in options.brbr----------brCHECK-OUT TIMEbr11AM is check-out. If you'll need to check-out after 11:00AM, and the night after your stay isn't booked yet, let's chat about late check-out options.brbrUnfortunately we do not have anywhere to hold bags after your stay.br---------brbrAIR MATTRESSESbrThere are two air mattresses in the property, both sleep incredibly well, and are kept in the closet of the 2nd bedroom, and hallway coat closet closest to the kitchen. Extra Linens can be found in the coat closet as well.brbr----------brPET OCCUPANCYbrTraveling with a pet This property is dog friendly! Once you book, please ask us for the digital pet request form.brbr-----------brGuest accessbrbrThe entire condo is yours during your stay! You will not share this condo with anyone outside of your own group!brbrGuests may request an early bag drop off as early as 1:00PM, we cannot guarantee that we will be able to accommodate, but we will try our best. In the cases that we can accommodate, bags can be dropped off after which time we ask that you leave the condo until 3:00PM to let the cleaners finish cleaning.brbrOther things to notebrPrivate parking is subject to availability – Please request parking accommodation prior to stay.brLicense numberbrR19000050240

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

Chicago, Illinois, United States

Bed

Bath

Sleeps

$2181.5

Loft606 Chicago is the perfect spot for private gatherings, weddings, corporate meetings, art exhibitions, reunions, dinner parties, birthday parties, classes, photo shoots, holidays, Bar Mitzvahs, and so much more. Loft606 Chicago offers events but are under a different pricing structure. Loft606 Chicago is between 3 of Chicago's hottest neighborhoods and walking distance from award winning restaurants, bars, and endless shopping. Our area has recently been named Chicago's New Restaurant RowbrbrIf that is not enough to keep you busy the ‘Western’ EL train stop is a short 2.5 blocks away. You will be a short trip by train or car to Downtown Chicago, Wrigleyville, Michigan Ave., Navy Pier, Lincoln Park Zoo, Millennium Park, the Museum campus, United Center, and the Lakefront.brbrLoft606 Chicago, this gorgeous 5,307 sq. ft. vintage industrial style loft is as unique as they come. Equipped with a 26' vaulted ceiling, and large skylights allowing ample natural light to fill the main room and massive gourmet kitchen.brbrbrExcessive noise, belligerence, smoking and/or vaping (inside and within 15 feet of an entrance), the removal or alteration of any item(s) on or belonging to the property (Humbled Hospitality) is banned at all Humbled Hospitality Properties. Please be respectful of the neighbors while at the venues by entering and exiting the properties quietly at night and not loitering outside.brbrAMENITIES:br• 2000sq.ft. living room w/ 26' timber beamed, vaulted ceiling and skylights running throughout.br• Newly stained concrete floors, exposed brick, vaulted ceilingbr• Sleeps 16 adults, in 6 rooms including a Master Bridal Suitebr• 2.5 bathrooms w/ a Jacuzzi and Rain-Shower in Master Suitebr• Massive, Gourmet kitchen with state-of-the-art appliancesbr• Beautiful Industrial Style Bar with full rear displaybr• Living Room/Lounge with Fireplace and Entertainment Centerbr• Our ‘Chapel Corner’ perfect spot to say ‘I Do’ under our crystal chandelier. br• Large Open Main Space, perfect for a dance floor between the kitchen, bar, and living room areas.br• Sonos Sound system & TV/cablebr• Large Disco Ballbr• Eclectic Décor br• Garden patio and Rooftop Deck with a Grillbr• Tables and Seating for 100 peoplebr• Three off-street parking spots (tight turn-compact cars only)/on-street parkingbr• Garage door access (for loading and unloading)br• Handicap accessiblebr• Pet friendly (fee)brbrAdditional Services (separate fee):br- Spa services provided by The Ruby Roombr- Bartenderbr- Additional Air Mattressesbr-Décor Removal/AdditionsbrbrbrTo provide you with the most accurate quote for Loft606 Chicago, please provide the following information in your inquiry. This will greatly facilitate us in booking our amazing space for you!brbr• What is the purpose of your stay (Wedding, Vacation, Reunion, etc.)br• Is the Stay for personal use or are you arranging this on someone’s behalf br• Who will be the on-site host during your stay What ages will your guests be br• What is your total guest count Are you expecting them all in the space at once or will they be in and out in groups br• How many people will be sleeping on the property br• Will any outside equipment, of any kind, be brought in br• Will you need or want any furniture moved/removed br• Will the kitchen be used br• Will you require any additional tables or seating br• Will there be a cover charge or fee of any kind for your guests br• If inquiring about an party: what are the hours, expected noise level, and budget for the function – Humbled Hospitality properties have alternate pricing structure for events.brbrThe more details, the faster we can welcome your group! We look forward to hearing from you here at Loft606 Chicago !

Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!

Chicago, Illinois, United States

Bed

Bath

Sleeps

$188.17

Experience the charm and convenience of our unique tiny apartment in La Vecindad, perfect for your stay in Pilsen, Chicago! This cozy 1BR, 1 Bath apartment accommodates up to 2 guests and features a cozy patio, providing a perfect retreat. Located just minutes from the train, you can reach Downtown Chicago in only 15 minutes.brbrEnjoy nearby attractions like the United Center, Harrison Park, Addams Medill Park, Soldier Field, Chinatown, and a variety of delightful Mexican culinary spots. La Vecindad offers a vibrant and inviting atmosphere you'll fall in love with.brbrNamed La Vecindad, the Spanish word for the neighborhood, our property captures the essence of community living. With a beautiful covered patio adorned with bricks and a comfortable lounge area, you'll feel right at home in this friendly and welcoming environment.brbrTraveling with a larger group Be sure to explore our additional properties available at La Vecindad. Book your stay now and make unforgettable memories!

Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

Chicago, Illinois, United States

Bed

Bath

Sleeps

$715.93

Charming & Comfy Gem ~ 10 Mins to Downtown ~Patio!

Chicago, Illinois, United States

Bed

Bath

Sleeps

$616.95

Experience a unique urban spa inspired retreat in Wicker Park, just a 5-minute walk from the Damen Blue Line.brbrNamed one of the hippest neighborhoods by Forbes, Wicker Park buzzes with energy, and Vital Urban offers the perfect balance—tucked away in a peaceful spot while keeping you close to all the action.brbrAfter a day of exploring, unwind in your private steam room, designed to melt away stress, or soak in the oversized jetted tub—your ultimate retreat from the city’s vibrant energy.

Vital Urban: Spa Inspired Retreat

Chicago, Illinois, United States

Bed

Bath

6

Sleeps

$673.7

Consider this house your home away from home while you visit Chicago. This superb property features five bedrooms, including four queen beds, one king bed, and a twin bed, perfect for families or groups. Guests enjoy three bathrooms equipped with showers and hair dryers for added convenience. Two additional living rooms offer cozy spots to relax, with a sofa bed, futon, and extra seating. The tranquil atmosphere makes it easy to unwind after a day of exploring. Experience what Chicago has to offer with a stay at our enjoyable house.

Spacious 5-bedroom house in charming Chicago on a quiet secluded block.

Chicago, Illinois, United States

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Bath

Sleeps

$1244.6

Welcome to our beautiful and spacious home in the trendy Logan Square neighborhood of Chicago! A short 3-minute walk to the Logan Square blue line, (15 minutes to downtown and 20 minutes to O'hare Airport), and a 3 minute drive to Interstate 90/94. 2 car garage with additional parking passes and tons of street parking. Located on a quiet street, fenced in backyard, with plenty of great restaurants, bars, and shops nearby. brbrThe home was specifically designed to ensure an amazing experience for all your guests. This is an ideal location if you're looking to live like a local; safe quiet neighborhood and a 6 minute walk to incredible bars and restaurants in Logan Square and quick trips via public transit or ride sharing to all that Chicago has to offer.brbrThe main floor is a beautifully designed open concept with a cozy sitting area overlooking the fireplace, a dining area, chef's kitchen, and living room. Directly off the living room is access to an outdoor patio, gas grill, and great outdoor space to enjoy (or curse) the Chicago weather. Beyond the outdoor space is a private 2 car detached garage.brbrUpstairs is the master bedroom with a king bed and ensuite bathroom, second bedroom with 2 queen beds and a desk great for your work from home needs, and third bedroom with two twin beds, and an additional full bathroom. The lower level has a fourth bedroom with a twin and double bed, a full bathroom, a small workout area with free weights and an elliptical, a second living room with a futon, and a washer and dryer.brbrOur home has lightning fast Wifi internet, 7 Smart TVs (one in each bedroom, living room, and workout area), Sonos speakers on the main and lower levels, tons of board games, pop-a-shot, a dart board, outdoor lawn games, a fire pit, and tons of outdoor seating. Bathrooms are always stocked with all the essential amenities (towels, shampoo, conditioner, body wash, q-tips, makeup wipes, toilet paper, hair dryer). The Chef's kitchen has dual ovens and high end appliances throughout with all the equipment, utensils, and supplies you need to make a 5 star meal.brbrYou will have access to our 2 car detached garage behind the home with app and garage door opener access. The front door and gate is secured by a code specific to your group.brbr24-hour access is available and the host is available for anything you may need - including a recommendation to the best entertainment in the area.brbrPlease let us know if there is anything else we can provide that would make your stay more enjoyable. Crib, high chair, Pack and Play, and dog beds available upon request.

Single Family Home in Logan w/ 2 Car Garage

Chicago, Illinois, United States

Bed

Bath

Sleeps

$393.31

Summary:brbrWelcome to your modern Chicago studio - a bright, thoughtfully designed space that combines comfort and functionality. Enjoy an open layout with a cozy sleeping area, a fully equipped kitchen, and a relaxing lounge corner. With natural light, sleek finishes, and all essentials provided, it’s the perfect home base for solo travelers or couples exploring the city.brbrbrbrThe Space:brbr• The apartment features a Full Bedbrbr• Huge windows offering spectacular views of the citybrbr• Washer & dryerbrbr• Fully-equipped kitchen brbr• Flat Screen TV/Cablebrbr• High-speed Internetbrbr• Stainless steel appliancesbrbr• Spacious, walk-in closetsbrbr• Individually controlled heat and airbrbr• Shampoo, conditioner, & body wash in bathroomsbrbr• Hair dryerbrbr• Iron/ironing boardbrbrbrbrAs part of our commitment to providing a premium experience, we offer complimentary starter items to kickstart your stay like shampoo, body wash, conditioner, hand soap, toilet paper, laundry detergent and kitchen supplies like coffee, tea, cooking oil, paper towels and seasonings. These items are thoughtfully provided to ensure you have everything you need upon arrival. However, please note that they are starter supplies and not be replenished during your stay. If you require additional supplies beyond the initial offering, we recommend local stores or delivery services for your convenience.brbrbrbrGuest Access:brbrEasy and convenient self check-in is available at this property. You’ll have full access to the apartment and building amenities during your stay.brbrbrbrThe Neighborhood:brbrPerfectly positioned at the crossroads of Old Town, Lincoln Park, and the Clybourn Corridor, this location lets you experience Chicago’s best mix of shopping, dining, and culture. Step outside to explore the New City shopping plaza, enjoy a show at the Second City Theater, or stroll along the North Branch Trail toward the lakefront. Within minutes, you’ll find stylish boutiques, gyms, Whole Foods Market, Trader Joe’s, and some of the city’s most beloved restaurants and coffee houses.brbrbrbrTransit: Multiple bus lines and the Red Line train nearby for direct access downtown and to the Loop.brbrCoffee: Sweetwaters Coffee & Tea (3 min), Printer’s Row Coffee (5 min).brbrDining: Boka, Ada Street, and Armitage Alehouse all within a short walk.brbrParks: Oz Park and the Lincoln Park Boardwalk are nearby for morning runs or weekend strolls.brbrbrbrWhether you’re here for work, leisure, or family time, you’ll love how easily connected this area is to River North nightlife, the Magnificent Mile, and Lake Michigan’s scenic paths.brbrbrbrGetting Around:brbrYou are minutes away from bus and train stops. brbrbrbrWe find some of our guests prefer to use Uber or Lyft, which is a very convenient and cheap way to get around the city.brbrbrbrOther Things to Note:brbrPlease note:brbr- The building features a central HVAC system that provides year-round comfort. Heating and cooling operate seasonally to keep the temperature pleasant. Guests can adjust the in-unit temperature within the range set by the building.brbr- Building maintenance staff may occasionally need access, but we’ll always provide advance notice whenever possible.brbr- Daily housekeeping isn’t included, though it can be arranged for an additional fee.brbr- Early check-in or late check-out may be available for $149 per service, depending on availability.brbr- On-site parking is available for $69 per night, per spot. Multiple spots can be reserved based on availability. Spots are limited and fill up fast - we recommend securing yours as early as possible. Please message us with your dates to reserve.brbr- Package delivery availability may vary by building - message us for details.brbr- Date changes that shorten or move a reservation follow the standard cancellation policy.brbrbrbrFor your security and a smooth check-in process:brbr- A refundable $500 security deposit is required.brbr- A valid government-issued ID and matching credit card must be provided before check-in.brbr- A short rental agreement will be sent electronically after booking.brbr- Some buildings may require a brief background check as part of management policy.brbr- Local residents (within two hours of the property) cannot book for same-day arrival.brbrbrbrWhile we strive to offer a peaceful experience, please be aware that city or building maintenance, construction, or temporary water/elevator servicing may occasionally occur. These events are outside our control and do not qualify for compensation.brbrbrbrInteraction with Guests:brbrOur online team is available 24/7 to assist you every step of the way - from booking to checkout, ensuring a smooth and comfortable stay.

Cozy Studio Suite, Steps from River North & Shops

Chicago, Illinois, United States

Bed

Bath

Sleeps

$2172.17

Cook in a dream kitchen with top-of-the-line appliances at this sprawling and luxurious home located on a quiet, one-way street. Completely updated with built-ins and molding, floor-to-ceiling windows, towering ceilings, patio, and fire pit—this home is exquisite.brbrEach level has an outdoor deck. Totally private courtyard.brbrTucked away on a quiet, one way street. Just steps to Breakfast, Restaurants and Bars. Yoga and spin studios, an amazing pizza spot, Whole foods, Starbucks and many more incredible restaurants and bars all within a block or two. Close to Wrigley Field, the Lake, Zoo, 606 and Southport Corridor.brbrIG: @jeremyalanbrown1

Luxurious Four-Level Home with Personal Touches Everywhere

Chicago, Illinois, United States

Bed

Bath

Sleeps

$598.0

Welcome to our luxurious 2-bedroom, 2-bathroom townhouse located in the heart of south loop Chicago! This home is perfect for travelers who desire a high-end experience, while still being in close proximity to all the city's major tourist attractions.brbrThis spacious townhouse features a modern design, with high-end furnishings and finishes throughout. You'll love the convenience of having two bedrooms, generously sized and flooded with natural light, creating a warm and inviting atmosphere. brbrEnjoy breathtaking views of the city from our rooftop terrace, where you can relax and unwind after a day of exploring. Our secure complex ensures your safety and peace of mind throughout your stay, while free parking provides a hassle-free experience for those traveling by car.brbrWith its prime location, you'll be just minutes away from all of Chicago's famous landmarks and attractions, including Millennium Park, Navy Pier, and the Mag Mile. Book now for an unforgettable experience in the Windy City!

Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!

Chicago, Illinois, United States

Bed

Bath

Sleeps

$114.89

Spacious & Comfortable Chicago Stay Near 95th Red Line | Fast Wi-Fi | Free Parking | Monthly DiscountsbrbrWelcome to your home away from home in one of Chicago’s most connected and community-centered neighborhoods.brbrLocated just minutes from the 95th Street Red Line train station, this property gives you fast access to downtown Chicago, museums, nightlife, events, and everything the city offers — without downtown prices or downtown congestion.brbrWhether you're visiting family, traveling for work, relocating, or just exploring the city, this space is designed to give you comfort, convenience, and peace of mind.br Prime LocationbrbrYou’re within minutes of:brbr• 95th Street Red Line Train Station (direct access to downtown Chicago)br• Tuley Park Cultural Center and Poolbr• Major grocery stores (Food for Less and Jewel Osco)br• Shopping centersbr• Restaurants & fast foodbr• Pharmaciesbr• Banks & essential servicesbrbrEverything you need is nearby, which means less driving and more enjoying your trip.brbr The SpacebrbrThis home is clean, organized, and thoughtfully prepared for short and extended stays.brbr Comfortable Sleeping Arrangementsbr• Spacious bed (Full size) with quality mattressbr• Fresh, professionally cleaned linensbr• Air mattress available for a third guest (additional guest fee may apply)brbr Cozy Living Areabr• Comfortable seatingbr• Mounted Flatscreen TVbr• Peaceful atmosphere perfect for relaxing after a long daybrbr Strong & Reliable Wi-FibrWhether you're working remotely, streaming movies, or attending Zoom meetings, you’ll enjoy a strong, high-speed Wi-Fi connection designed to handle multiple devices with ease.brbrFully Equipped KitchenbrbrAll major appliances are available and grouped for convenience:brbr• Mini Freezerbr• Mini Ovenbr• Microwavebr• Coffee makerbr• Plates, bowls, and glasswarebrbrWhether you’re meal prepping for the week or just making coffee in the morning, everything you need is here.brbr Cleanliness & ComfortbrbrI take cleanliness seriously. The space is thoroughly cleaned and prepared before every guest arrives.brbrFresh towels. Fresh linens. Sanitized surfaces.brbrYou won’t walk into surprises.brbrbr The NeighborhoodbrbrThis area offers a strong sense of community and accessibility. It’s residential, welcoming, and close to everything important.brbrYou’re literally about 3 houses from Tuley Park where you can enjoy:brbr• Outdoor walking pathsbr• Pool access (seasonal)br• Open green spacebrbrThe neighborhood is active and well-traveled due to the nearby train station and shopping centers, which adds convenience and visibility.brbrbrShopping & Essentials NearbybrbrWithin minutes you’ll find:brbr• Major grocery storesbr• Starbucksbr• Wing Stopbr•Subwaybr•Hot Chi Chickenbr•Foot Lockerbr•Dollar Treebr•Home Depotbr•Mcdonaldsbr•Harolds Chickenbr•Burger Kingbr•Grand Chinese Kitchenbr• Coffee shopsbr• Planet FitnessbrbrYou won’t need to drive across town for daily necessities.brbr Upcoming Chicago EventsbrbrChicago is always hosting events — concerts, sports, festivals, and conferences. Staying near the Red Line makes getting to downtown events easy and affordable.brbrAvoid expensive downtown hotels and stay somewhere spacious and connected.brbrbrPet PolicybrbrPlease inquire about pets before booking.brbrPet approval is case-by-case. Unauthorized pets may result in additional cleaning fees.brbr House Rules & Quiet HoursbrbrTo maintain comfort for everyone:brbr• Quiet hours: 8:00 PM – 8:00 AMbr• No partiesbr• No unauthorized guestsbr• Respect neighbors and propertybrbrThis is a peaceful space designed for respectful travelers.brbrCheck-In & Check-OutbrbrCheck-In: 3:00 PMbrCheck-Out: 11:00 AMbrbrIf you need flexibility, send a message and I’ll do my best to accommodate when possible.brbrNeed Additional Services brbrLooking for a housekeeper during your stay Let me know in advance and I can help coordinate options.brbrEmergency InformationbrbrIn case of emergency, dial 911.brbrNearby hospitals and urgent care facilities are easily accessible from the property.brbr Instant Booking AvailablebrbrFor your convenience, instant booking is enabled. If your dates are available, you can secure your stay immediately.brbrThe calendar has been filling quickly — if you're considering booking, send a message to secure your reservation.brbrIf you're traveling on a budget, reach out. I’m open to discussing reasonable stays, especially for longer visits.brbr Monthly Discounts AvailablebrbrStaying longer Ask about monthly discounts. This space is ideal for:brbr• Traveling professionalsbr• Nursesbr• Contractorsbr• Remote workersbr• Relocating familiesbrbrExtended stay pricing makes it a smart alternative to hotels.brbrbrbr Smart Pricing for GuestsbrbrRates may adjust based on seasonality and local events to remain competitive and fair.brbrAbout Your HostbrbrI’m passionate about giving guests an extraordinary experience. I’m approachable, organized, and driven. Communication is clear and timely.brbrMy goal is simple:brYou arrive comfortable.brYou stay stress-free.brYou leave satisfied.brbr---brbr## Why Guests Choose This Propertybrbr✔ Close to public transportationbr✔ Strong Wi-Fibr✔ Clean and organizedbr✔ Comfortable bedbr✔ Fully equipped kitchenbr✔ Near shopping & groceriesbr✔ Monthly discounts availablebr✔ Responsive hostbrbr---brbrIf you're ready for a smooth, convenient, and comfortable Chicago stay, send a message now.brbrI’m excited to host you and your travel buddies.brbrLet’s get your dates secured.

Private Basement Suite-Completely separate from the rest of the house

Chicago, Illinois, United States

Bed

Bath

Sleeps

$392.38

Come stay at our luxurious downtown view in a new construction in Chicago. This centrally located, gated, 3Bedroom, 3Beds, 2bath suite is ideal for family vacation, work or leisure trips. It comes with a full upscale gourmet kitchen with coffee machine and 2024 with appliances. Watch all live TV/Sports for free! 8mins drive to the best attractions in Chicago, including the beach and museums; close to numerous restaurants, nightlife, and major highways for easy travel and access around the city.

LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

Chicago, Illinois, United States

Bed

Bath

Sleeps

$579.99

Fun times with family and friends at this stylish beautiful home located 10 mins from Hyde Park, (Tiger Woods) Golf Course, Downtown, Soldiers Field (Chicago Bears Stadium), Northerly Island Concerts, Taste of Chicago, Lalapalooza, Museums, Zoo, Millennium Park & tons of other sights in Chicago!brbr5 mins from Univ. of Chicago, Obama Library (coming soon), the beach, and Museum of Science and Industry.brbrPerfect place to stay if you are coming with a group for a convention at McCormick.

Woodlawn Oasis...10 Minutes to Dining & Downtown

Chicago, Illinois, United States

Bed

Bath

12

Sleeps

$1638.0

Experience Chicago from the comfort of this MASSIVE 6 bdr/6 bth home in Avondale!brbrWhy you'll love this 3 floor home:br- PRIVATE rooftop deckbr- TWO kitchens complete w/everything you needbr- HIGH-END mattresses, pillows, and beddingbr- FOUR King beds & 4 queen bedsbr- Steps to great restaurants, Blue Line train to downtown & 90/94 freewaybr- Kids play areabr- FREE 2 car garagebr-Several family rooms to gather w/ friends & familybr- Exercise equipment (bike, yoga mats, etc)br- TWO sets of laundry machinesbrbrSleeps 15 guests!! Complimentary garage parking! brbrWelcome to our warm and inviting, Nora Ephron inspired home in the Avondale neighborhood, a foodie haven near Logan Square. It's just 15 min to downtown Chicago by train. brbrWe designed this house to be your home away from home: a high-end, vintage-inspired retreat where every detail has been thoughtfully curated. This spacious home blends timeless charm with luxury living, perfect for multigenerational family stays, business groups, bachelorette getaways, college reunions, and everything in between. brbrbr**Sleep in Comfort & StylebrEnjoy blissful rest on premium mattresses topped with down-filled duvets, plush pillows, and a mix of French linen and cotton bedding from The Citizenry, Hotel Collection, West Elm, and more. With four KING beds, everyone has room to stretch out and relax in comfort.brbr**Fully Equipped KitchenbrOur main kitchen is ready for anything from morning coffee to a full dinner spread. Equipped with high-quality stainless steel cookware, sharp knives, abundant utensils, and full sets of dinnerware. Of course, there's a generous supply of coffee and tea for your mornings.brbr**No Waiting for ShowersbrWith 6 beautifully designed bathrooms (5 full, 1 half), your group can get ready without the hassle. Each space is thoughtfully styled and stocked for comfort.brbr**Family-Friendly FeaturesbrTraveling with kids We’ve got you covered with a Greenguard Gold Certified crib by Namesake, high chair, baby walker, and a dedicated playroom featuring a real cedar playhouse, KidKraft play kitchen, and more kid-friendly touches. (Please request crib and high chair ahead of your visit).brbr**Prime Location in ChicagobrLocated just 3 miles from Wrigley Field and only 3 blocks to the Belmont Blue Line, getting downtown or to other major attractions is a breeze via public transit or the nearby Kennedy 90/94 expressway. Walk to grocery stores like Jewel-Osco and Target for easy stocking up during your stay.brbr**Other things to note**brI look forward to hosting you, but **before** you book:brbr-No parties allowed on the property. Local groups looking to use the property for a party are expressly prohibited and your reservation will be canceled.brbr-No outside visitors or extra guests without prior approval from the host. By booking, you agree that there will be no unannounced guests other than the number of guests you have on your reservation.brbr-*No marijuana OR tobacco smoking* is allowed in the house. It lingers in the carpets, walls, and curtains. We also prohibit smoking within 15 feet of any entrance. If there is evidence of smoking, including odor, there will be a $400 smoke remediation charge.brbr-No pets (I love them, but not allowed here). Unauthorized pets will incur a $300 fee.brbr-For liability and insurance purposes we have Ring cameras and motion sensors on the EXTERIOR of the building (none inside).

6 BDRM/ 6 BATH LUX Avondale Home, Sleeps 15, Rooftop Deck & 2 Car Garage!

Chicago, Illinois, United States

Bed

Bath

Sleeps

$935.59

Welcome to a newly built luxury 6 bedroom house in Chicago’s family friendly Albany park neighborhood. Centrally located - close to downtown (25 min), Wrigley Field (15 min) and O`Hare (15 min)brbrLarge common areas and a chefs kitchen with a 5 person island allows large parties and families to stay comfortably. The house offers spacious rooms and a full laundry room on the second level. brbrThe home also includes a 2 car garage and the convenience of not having to worry about parking in Chicago!brbrMain level - living areas laid out to take advantage of light, dining areas, and a large kitchen. There`s a half-bath on this level as well. brbrUpstairs - Master bedroom with king bed and ensuite bathroom, three additional bedrooms with queen beds, and another bathroom. brbrLower level is a family room, two bedrooms with queen beds, and a full bathroom.brbr6 Bedrooms, 3.5 Baths: Plenty of space for everyone to spread out comfortably.brbrGourmet Kitchen: Fully equipped with stainless steel LG appliances, island seating, and a pantry.brbrCentral Air & Zoned HVAC: Stay comfortable year-round with dual-zoned heating and cooling.brbrCovered Deck & Large Backyard: Perfect for outdoor dining and enjoying the Chicago weather.brbrFinished Walk-Out Basement: Additional living space, bedroom, office/den, and full bath.brbrIn-Unit Laundry: Full-size washer and dryer for your convenience.brbrTwo-Car Detached Garage: Secure off-street parking. Free street parking as well.brbrHigh-End Finishes: Recent gut rehab (2019) with thoughtful details throughout.brbrCheck-in is effortless and 100% contact-free. Your private access code works on all exterior door keypads, allowing you to arrive and settle in on your own schedule. We’ve designed the process to be completely autonomous, though our team is always just a message away if you need us!brbrLovely diverse neighborhood with restaurants to explore such as;br· Authentic Lebanese cuisine at Semiranisbr· Persian food at Noon-O-Kebabbr· Swedish dishes at Tre-Kronerbr· Korean Barbeque at Chicago Kalbibr· Filipono food at Merlas Kitchenbr· Flaky, pistachio baklava at Middle Eastern bakery Jaafer Sweetsbr· Delicious boutique wine at Angelos Wine Barbrbr*This home is professionally curated by Hosty Co, Chicago’s premier boutique management team. We specialize in high-touch service, 5-star aesthetics, and seamless stays.*brbr**Follow the journey: Find us on social @hosty_co_chibnb for a look at our full portfolio and `insider only` Chicago neighborhood guides.**brbrTo protect the quality of our home and the harmony of our neighborhood, we specifically host:br*Corporate Travelers seeking a refined, reliable home base.br*Families visiting for holidays or major Chicago milestones.br*Urban Explorers who value a quiet, high-end retreat.brbrBooking Requirements: We operate under a strict `Good Neighbor` policy. To ensure we are the right fit for your trip:br*Tell Us Your Story: When inquiring, please include a brief note about your trip and your group. We love knowing how to best prep the space for your arrival!br*Vetting: We prioritize guests with 100% ID verification and a track record of positive reviews.br*Zero Tolerance: To maintain our home`s integrity, parties and unauthorized gatherings are strictly prohibited.brWe ask that guests do not wear shoes in the house and respect our neighbors with quiet hours.

Stunning 6 BR Home * Chicago * Centrally Located

Chicago, Illinois, United States

6

Bed

Bath

12

Sleeps

$217.28

Welcome to our charming garden flat in Chicago! This private-entry unit features 2 bedrooms—one w/ a king bed—a renovated kitchen, inviting living/dining areas, & a small desk for remote work. As a garden unit, ceilings are slightly lower but it remains bright & cozy.brbrPerfectly located between O’Hare and downtown, with a bus stop right outside connecting you to the Blue, Brown, & Red lines. Free street parking, nearby parks, & restaurants. brbr13 min to Wrigley Field | 20 min to Willis TowerbrbrThe Space:brbr-Private 2-bedroom, 1-bath basement apartment in a traditional Chicago two-flatbrbr-One bedroom features a KING bed and the second bedroom features a QUEEN bedbrbr-Entire apartment is private and exclusively available for your staybrbr-Smart TV with streaming apps available (guests use their own logins)brbr-This unit includes a kitchenette setup with a fridge, stovetop, microwave, toaster, dishwasher, sink, and Keurig coffee machine. Please note there is no oven in this unitbrbr-Clean linens, towels, shampoo, conditioner, body wash, and starter supplies provided prior to arrivalbrbr-Free street parking available nearby on a first-come, first-served basisbrbr-Washer and dryer are located in a shared utility/laundry room in the basement and are shared with the other units in the building. The laundry machines are not located inside the apartment itselfbrbr-Please note this is a basement unit, so ceiling heights are slightly lower than a standard apartment. Taller guests should be aware of this prior to bookingbrbr-This is a multi-unit residential building, so occasional neighbor noise or footsteps from the upstairs unit may be heard. We installed noise-reducing spray foam insulation to help minimize sound transfer as much as possiblebrbr-Chicago quiet hours must be observed between 10pm–8am dailybrbrGuest Accessbrbr-Entry to this apartment is through a side door, which leads to private entrance in the basementbrbr-Check-in instructions and access codes will be provided prior to arrivalbrbr-Early Check In is available for an additional charge of $50, but is subject to availability. Please message the host to confirmbrbr-Late Check Out is available for an additional charge of $50, but is subject to availability. Please message the host to confirmbrbrOther Things To Notebrbr-Absolutely no parties, gatherings, unauthorized guests, or smoking of any kind are permitted on the propertybrbr-Violation of house rules may result in additional cleaning or damage fees of up to $400 and immediate cancellation of the reservation without refundbrbr-Outside decorations including confetti, glitter, balloons, candles, streamers, banners, or wall adhesives are not permittedbrbr-Starter supplies are provided but guests may need to replenish additional items during longer staysbrbr-Please report any issues during your stay as soon as possible so we can address them promptly. However please keep in mind that our availability is limited during after hours between 10pm-9ambrbr-Please remember this is a home and not a hotel. We strive to provide a clean, comfortable, and enjoyable stay for every guest

Charming Garden Flat w/ King Bed

Chicago, Illinois, United States

Bed

1

Bath

Exceptional(17)

$907.29

Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of art deco and Scandinavian design.brbrThe home is conveniently located in ‘Lakeview’ with a 20min walk to Wrigley Field and 10min to the Brown Line. And if you're driving, we offer free dedicated parking for THREE vehicles.brbrOur home is a duplex with two spacious & connected living spaces. Each space is similar in design with their own unique touches. As such you'll have access to 6 bedrooms, 2 bathrooms, 2 living spaces, 2 dining rooms, a huge backyard, and 3 car carport.brbrWe've taken time to curate an incredible experience for our guests. Check out our bedding accommodations and favorite features:brbrBedding Accommodations (Sleeps 17+):br- 2 Queen Size Bedsbr- 1 Full Size Bedbr- 2 Full + Twin Bunk Beds (i.e. it's a cool bunk bed not a regular bunk bed)br- 3 Twinsbr- 2 Couches (Comfy AF)brbrFor larger groups, air mattresses & cushioned cots with extra bedding are available upon request.brbrOur favorite home features:br- 3 car carport br- 2 beautiful walk-in showersbr- Frontlit LED bathroom mirrorsbr- Spacious backyard w/ firepit and string lights br- Keurig with complimentary coffeebr- 2 Make-up Desksbr- Keypad self-check-inbr- High-speed fiber optic internetbr- Well-equipped kitchen with common seasonings, olive oil, penne pasta, and rice.br- Memory Foam Mattresses br- Pack & Play Cribbr- In-unit washer & dryerbr- 65in Smart TV with streaming apps pre-downloaded

Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+

Chicago, Illinois, United States

Bed

Bath

Sleeps

$424.16

Discover the beauty of Chicago from this 3-bedroom luxury house. Guests will find a tranquil space featuring one king bed, one queen bed, and one twin bed. The house includes three bathrooms, one with a jetted bathtub for a relaxing soak. Four additional rooms offer extra comfort—a living room with one queen sofa beds with office. Outdoor private patio for entertaining with a Grill masters touch. Whether you’re unwinding or working, this awesome home provides an enjoyable stay. 20 blocks from Willis Tower and 10 minute Uber ride to Michigan Ave and walking distance to White Sox’s park. We're happy to assist with any questions while you stay at our house.

Location, large luxury house - safe and close to everything.

Chicago, Illinois, United States

Bed

Bath

8

Sleeps

$523.5

Consider this townhome your home away from home while you visit Chicago. This tremendous space features four bedrooms, including a king bed, a queen bed, and three full beds, perfect for families or groups. Guests can refresh in any of the three bathrooms, each equipped with a shower and a bathtub for a soothing experience. The serene atmosphere invites relaxation after a day of exploring. Whether you’re gathering in the spacious living areas or unwinding in your private room, comfort is always within reach. Enjoy all that Chicago has to offer when you stay at our place.

Marvelous 4-bedroom townhome with Free Parking in vibrant Chicago

Chicago, Illinois, United States

4

Bed