Loft holiday rentals in Downtown Chicago

Modern LOFT Ukrainian Village 2nd floor

Private, Bright 2nd floor Loft with Tall Ceilings with Lots of Light. Creative Decor with Artwork and Artifacts. Relaxing and Cozy. Tree Top View of the Garden. Everything you need for a Long or Short Time Stays. Stocked Kitchenette, Modern Bath, Laundry and Fast WI-FI . Perfect for 1 or 2 for work or play. The Street is Quiet, Conveniently Located just 1 block from Bustling Division Street in Wicker Park, Downtown, the Blueline to all Airports and 1 Mile from the New Salt Shed Music 🎵 Venue

West Town Traveler's Lodge

Come and stay at my gorgeous 2 bedroom 1 bath condo! It's in a wonderful neighborhood, and in an ideal location for hopping around the city. It's a perfect place to re-energize between big city adventures--> just a 7-10 min walk to the Division St Blue Line Station (3 stops to The Loop). Hardwood floors, granite counter tops, high ceilings, a large back patio, some cool furniture, and exposed brick await in this charming West Town loft. Easy access to both airports via public transit is a plus!

1920s fully updated unique open artist loft space

True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

Downtown Penthouse #5 | Vintage +gym & balcony

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! We are a short walk to Millennium Park, Skydeck, Shedd Aquarium, Adler & many dining + shopping options! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ NEW HVAC Split Units ✅ It's Unique! ✅ High loft ceilings ✅ FAST WIFI ✅ Spacious layout ✅ Comfy beds ✅ Central Location ✅ Big Balcony! ✅ Close proximity to Grant Park, Soldier Field, Museums, and more!

Tea Studio in Wicker Park Spring Factory

There's no other place like it in Chicago. A converted 1900's warehouse in the heart of Wicker Park - Once a Prohibition-era distillery, then a spring factory, and finally reimagined as a one-of-a-kind designer loft. Features soaring 14-foot timber ceilings, exposed brick, and a level of finish that earned a national kitchen award and a feature in TimeOut's "Best in Chicago". The kitchen is massive. The bathrooms are luxurious. Plus, Chicago's best neighborhood is right outside the door.

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

Wicker Park Loft w/ Free Parking; Easy DWTN Access

Stay in a modern 3-bedroom, 2-bath Airbnb in Wicker Park, Chicago, located at the prime intersection of North Ave & Ashland. This updated unit features stylish finishes, spacious living areas, and free on-site parking, a rare find in the city. Just 10 minutes from downtown, you’re close to top attractions, dining, nightlife, shopping, public transit, and everything Wicker Park has to offer—perfect for families, groups, or business travelers. Free designated parking to top it off.

Modern, Stylish West Town Loft with Pool Table

Spacious, open, and modern, my two bedroom loft is the perfect spot to welcome you to the Windy City. All the comforts of home are provided to you to ensure a comfortable stay. Downtown is just 10 minutes away, and there's plenty to do within walking distance as well! You'll love exploring the city from this centrally located base, coming back in the evening to shoot some pool and unwind, and resting up to do it all again the next day. Don't miss out on this gem, book today!

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Loft8 - Unique Design in Prime Location

Welcome to your dream Chicago getaway! This stylish, two-story loft is perfectly located in Wicker Park. One of the city’s most vibrant and iconic neighborhoods. Whether you're here to explore buzzing restaurants, indie shops, or nightlife just steps away, or you’re kicking back in a beautifully designed space, this is the kind of stay that makes you never want to leave. ✨ Superhost hospitality 🛏️ Designed for comfort 📍 Walk to everything 💫 5-star guest-approved

OHC Gorgeous Huge Studio Apt Steps to Blue Line

Welcome to OHC Studio! Part of the Open House Contemporary family of art gallery airbnbs, this huge 1000 sq ft studio apartment is the perfect place to call home base while you explore Chicago. Featured in Architectural Digest (Aug. 2018) and as one of Bobby Berk's (Queer Eye's designer extraordinaire) top 10 Airbnbs in Condé Nast Traveler (Sept. 2018).

Bright & Spacious Noble Square Loft

Bright and spacious top floor loft in Chicago's Noble Square neighborhood. Walk to food, drink, fun and shopping. Easy access to ZipCars and public transportation (bus, train, and METRA). Quick trip to Michigan Ave, Lakefront and Navy Pier. A quick 5 minute ride to nightlife in the Wicker Park / Bucktown neighborhood.