Loft vacation rentals in Downtown Chicago

4.95 out of 5 average rating, 150 reviews

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

Superhost

Two large windows are framed with white trim, allowing natural light to fill the space. The exposed brick wall provides a rustic backdrop, while greenery is visible outside, creating a connection with the outdoors. A small keyboard rests on the floor beneath the windows.

4.86 out of 5 average rating, 669 reviews

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!

An open-concept loft showcases a cozy seating area with a grey couch adorned with yellow and patterned throw pillows. The kitchen, visible in the background, features modern appliances and a bar with two stools. A lofted sleeping area is bordered by a wooden railing.

4.96 out of 5 average rating, 241 reviews

Lincoln Park Light-Filled Loft

Experience this unique Lincoln Park loft where you’ll love the open concept space, the floor to ceiling windows & the conveniences of your own two level suite. A converted store-front, this space is perfect for a couples weekend in Chicago, that friends get-away, or a place to call home for your small family vacation. Walk the neighborhoods & parks, and wonder why you’re not staying longer. We call this our little gem of a find, and are excited to share it with you. We love it, so will you!

4.91 out of 5 average rating, 159 reviews

A spacious artist loft features a living area with hardwood floors and large windows allowing natural light. A leather sofa is positioned in the center, with stylish chairs nearby. The open kitchen is visible in the background, along with a modern dining space under soft lighting.

Loft in Brookfield

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

The open living area showcases a large, comfortable sectional sofa in a warm orange hue, complemented by a round wooden coffee table. A flat-screen TV is mounted on the wall, and decorative artwork is visible. Natural light filters through sheer curtains, illuminating the space.

4.76 out of 5 average rating, 247 reviews

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!

The spacious open-concept living area features a modern kitchen with a central island and bar seating. A cozy seating arrangement includes a black leather chair and a circular coffee table. Natural light floods the room through the overhead circular skylight, enhancing the inviting atmosphere.

4.85 out of 5 average rating, 158 reviews

Luxury Penthouse Loft - Heart of Fulton Market

NEW PENTHOUSE LOFT IN FULTON MARKET! Enjoy your own private luxury loft in Chicago's bustling Fulton Market-the city's center of main nightlife, restaurants and cultural scene. This 3,500 square foot penthouse features 12 foot open lofted ceilings, a dedicated elevator entrance, free onsite garage parking, 5 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

A modern kitchen features a large stainless steel island with seating for three. Black cabinetry offers ample storage space, complemented by open shelves displaying various kitchen items. Pendant lights hang above, illuminating a stylish workspace adorned with greenery, while industrial elements add character.

4.96 out of 5 average rating, 292 reviews

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.

A contemporary loft bedroom features a spacious bed with a light grey quilt. Exposed brick walls complement framed vintage Chicago artwork. Soft lighting is provided by string lights near the window. A green plant adds a touch of nature, while dark wood accents create warmth.

4.96 out of 5 average rating, 567 reviews

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.

Superhost

4.91 out of 5 average rating, 227 reviews

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.

Superhost

An open living space is featured, showcasing a pool table at the center. A staircase spirals to the upper level, while a dining area and modern kitchen are visible in the background. Natural light fills the area, enhancing the spacious atmosphere.

4.81 out of 5 average rating, 135 reviews

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!

A modern living space features a light-colored sofa with decorative pillows and a woven throw. A warm-toned wooden accent wall complements a sleek electric fireplace below a mounted television. A patterned area rug anchors the room, while shelves in the background display decorative items.

4.99 out of 5 average rating, 138 reviews

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.

An open-concept living space is highlighted by high ceilings and large windows, allowing natural light to flood the area. A stylish kitchen features modern appliances, while the living area includes a comfortable sofa and accent chairs. A dining table and greenery add warmth to the atmosphere.