Loft vacation rentals in Chicago

4.92 out of 5 average rating, 248 reviews

A bright loft space is highlighted by exposed brick walls and sunlit windows. A comfortable nook with cushions overlooks the lower living area, featuring a pool table and modern furnishings. Light wooden beams and a high ceiling enhance the spacious atmosphere.

Loft in Old Town

Stunning Old Town Penthouse with Private Rooftop

This listing is for the entire building, which is the combination of a penthouse loft (3BR) and the unit directly underneath (2BR), easily connected by private stairs. You will also have a private rooftop deck. This is a beautiful 4,000 sq. ft penthouse loft combined in the heart of downtown Chicago. The building is next to "Magnificent Mile" and steps away from amazing restaurants, comedy clubs (Zannies, Second City), theaters, boutique shopping, public transportation (red line, and 156 bus line), bars and just four blocks from the beach. **Please be aware there are 45 steps to get into the unit (2 flights). This building is truly one of a kind. Built in 1897 and completely renovated in 2016 this unit has exposed brick, 20 foot ceilings and 120 year old barn wood floors capped off with a rooftop deck overlooking Willis (Sears) Tower. 5 bedrooms - 4 with king beds and one with 3 single beds (a bunk bed and a separate single) Also a nook area with a twin bed, built in reclaimed wood; very cute, unique, and comfortable sleeping area! 4 full bathrooms Two full kitchens and two full living rooms. Penthouse master bedroom- Fit for a king. Located on balcony level overlooking living room. Vintage french doors open to balcony. Furnished with a tempurpedic king sized bed and 50 inch TV. Attached to marble bathroom with jacuzzi and all-marble rain forest dual shower head steam shower. Enjoy Kohler faucets and heated floors. (All assortments of toiletries, blow dryer, extra towels, linens, and extra pillows and blankets included) Penthouse second and third bedrooms - Spacious and comfortable, king bed in one, three singles in one. Nicely outfitted with crown molding and large closets. Second Bathroom - Marble floors, classic European style and granite counter tops. (All assortments of toiletries, blow dryer, extra towels and linens included) Fourth bedroom - Furnished with a cloud like king sized bed, crown molding, exposed brick, and large closet. Remote controlled overhead fan. Connected to a brand new subway tiled bathroom with antiqued brass hardware and a jacuzzi. Enjoy heated floors here as well. (All assortments of toiletries, blow dryer, extra towels, linens, and extra pillows and blankets included) Fifth bedroom - Spacious and comfortable, with cloud like king bed. Crown molding, exposed brick and large closet. Remote controlled overhead fan. Fourth Bathroom - Subway tiled walls with antiqued brass hardware here as well, classic European style marble counter tops. (All assortments of toiletries, blow dryer, extra towels and linens included) Extra amenities include two push button fireplaces, vintage 1950 Valley pool table, dartboard, surround sound stereo system, PS3 (with movies and games), blu ray, board games and two 60-inch hanging TVs both equipped with HBO, Netflix, Showtime, TiVo, and Amazon each in their own full sized living rooms. Two full laundry rooms in building with irons and ironing boards. Last but not least is the private rooftop deck. This view is absolutely magnificent. Your first walk out onto this large spacious rooftop deck will leave you speechless. It boosts a comfortable couch, grill, and large table all adorned with round draping bulb lights going from corner to corner of the deck, with a full 360 degree view of the Chicago skyline. You will never forget your Chicago visit when you are on the roof deck after the sunsets and the city lights fill up the sky. Spoil yourself in the Windy City. There is nothing else like this in the city. Upon arrival, a welcome packet that will explain to you all about the features of the penthouse and how to maximize your time while staying here. Anything from how to work the jacuzzi to how to operate the electronics is outlined and at your disposal when you walk in the door. We are also pet friendly. While exploring the city we are very centrally located we recommend walking or biking to places like Michigan Ave and the Oak Street beach. A wonderful place to spend an afternoon! There is a parking garage across the street for $26/day located at 1225 N Wells Street. There is also metered street parking. Old Town is an historic area of Chicago right in the middle of the action. It's a perfect base from which to experience the city. Walk or bike to interesting places like Michigan Avenue and the Oak Street Beach. We are very close the the Red Line El train and numerous buses and a divvy bike station. Parking garage across the street. Uber and Lyft are choice methods as well. However, being in the heart of Old Town there is plenty within walking distance.

Top guest favorite

A modern living area features a working fireplace framed by a sleek stone wall. An artwork depicting a scenic waterfront view is hung above the fireplace. A decorative basket holds lush green plants, complementing the warm tones of the leather seating and the dark wooden floor.

Loft in Forest Park

4.96 out of 5 average rating, 507 reviews

Walk to Oak Park from a Bright Madison Street Loft

Crowned "The best in neighborhood dining" according to a 2008 Chicago Tribune readers poll, the variety of Forest Park restaurants offer something for everyone. The unit is a charming two bedroom, two bath loft a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 20 minute train ride away. The condo includes additional amenities such as: - Elevator in building •Secure front and back entrances. •One assigned parking spot in the back of the building. •Full kitchen with stainless steel appliances (stove, dishwasher, refrigerator), cookware, and dinnerware. •Granite countertops. •Two full bathrooms. The master bathroom includes a Jacuzzi tub. •Two full bedrooms. Both have queen sized beds. •Smart TV with cable access and access to Netflix. •Central Air conditioning •Working fireplace •Balcony with a view of downtown Chicago's skyline •Washer and dryer in unit. Just to the east lies historic Oak Park, which offers an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After soaking up some attractions in Oak Park, Chicago is only a short twenty minute train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry The loft and both doors to our building have key-less entry pads. We will email you your personal entry code along with check in instructions a couple days before your arrival. Each guest is given their own personal code. Codes are programmed the day of check in and deleted shortly after check out. We are as available as you need. Centrally positioned in the Madison Street shopping and dining district, the loft is conveniently surrounded by local eateries and pubs within minutes of downtown Chicago and the United Center, and just blocks from the CTA blue line. We are located half a mile from the L - Blue Line. We are the Forest Park Stop on the blue line. The blue line will take you into the city. It is about an 8 to 10 minute walk from the loft. An Uber/Lyft ride into the city ranges from $15 to $25 and takes around 15 to 20 minutes. We are one mile from the Metra train line (Union Pacific - West). The Metra dead ends into Union Station. There are a number of Metra lines that take you to surrounding suburbs. We are also one mile from the Green Line - Oak Park Stop. The Green Line is another line on the L. The third bed is a queen sleeper sofa. There is a strict no smoking policy in our building. You can not smoke on the balcony - it will result in a $500 fine. The neighborhood is vibrant in the summer and sound can travel into the unit.

4.86 out of 5 average rating, 646 reviews

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.

Loft in West Town

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!

4.89 out of 5 average rating, 112 reviews

The kitchen features sleek shelving showcasing glass jars and wine bottles, complemented by ambient light fixtures. A coffee machine and sink are positioned on a dark stone countertop, with a dishwasher integrated into the cabinetry for convenience.

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

A smart lock is displayed on the door, featuring a numeric keypad illuminated in blue. The visible numbers range from 0 to 9, with a keyhole positioned underneath, providing a modern and secure entry option.

4.77 out of 5 average rating, 555 reviews

Wicker Park Loft - Walk To Everything!

Walk to Bucktown & Wicker Park bars, restaurants & shopping from this large apartment in working artists' building. 10 minute WALK to CTA Blue line TRAIN. FREE STREET PARKING. Premium mattresses and all essentials provided. Resident artists work on the first floor of this historic former telephone repair and switching station. Very laid back vibe. NOTE All guests must be on your reservation for an accurate $total. There is a $30 per night/ per guest charge AFTER 2 Guests (3rd to 5th)

Loft in Pilsen Historic District

A sunlit kitchen area with white cabinetry and stainless steel appliances is showcased. A bright yellow wall complements mid-century-style furniture, featuring a light blue chair. Large doors open to the balcony, allowing natural light to fill the space.

4.9 out of 5 average rating, 390 reviews

Pilsen Modernist, Creative, Lightfilled Loft

Take morning drinks through the sunshine-yellow room to the back porch, or watch light dance on translucent walls and glossy black and white hardwood floors. Eclectic design includes a mix of new and vintage furniture, and a collection of art and design books for guests to enjoy. This unit is owned by an artist couple who split their time between Tucson, AZ and Chicago. This is their personal unit when they're in Chicago. Come stay here to get away, be comfortable, relax, and be inspired.

4.96 out of 5 average rating, 509 reviews

A vintage-inspired living area is highlighted by a textured wooden wall and exposed brick. A large television is mounted above a sleek coffee table, with wall-mounted lanterns adding ambiance. A small potted plant sits at one side, contributing a touch of greenery to the space.

Loft in Lake View

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.

An open living area features a light gray sofa adorned with colorful throw pillows. A wooden coffee table is positioned in front of the sofa. The space showcases a decorative rug and a wall of exposed brick, complemented by elegant lighting fixtures and large windows allowing natural light.

4.89 out of 5 average rating, 139 reviews

Entire Loft in Heart of Wicker Park with Parking

Entire floor in one of the coolest neighborhoods of Chicago. You will have access to whatever you desire right here, from it’s amazing abundance restaurants, shopping and cafes to walking the almost three mile walkway of the “606” and it’s rotating installations, observatory and relaxed vibe. At the end of your day you’ll love heading back to your wide open space with its retro inspired furnishings with just the right amount of modern amenities and comfort.

4.82 out of 5 average rating, 253 reviews

An open loft space features original wood floors and a cozy clawfoot tub near the living area. A long vintage dining table accompanies a mix of wooden and wicker chairs. Natural light floods the space through large windows, highlighting the room's unique architectural elements.

Loft in Logan Square

Quirky Bucktown Loft w/ Parking No Parties

Located on a peaceful treelined street in energetic, fashionable Bucktown with upscale amenities at your fingertips. This unique penthouse/loft apartment has its share of quirks that come with being a 125-year-old building yet its unique vintage comfort, eclectic furnishings and modern necessities come together to make your time in the city relaxing and unforgettable. This is a legally licensed Chicago vacation rental R22000079930

A modern living area features a light gray sectional sofa, complemented by a low coffee table and a stylish area rug with dark and light stripes. Exposed brick walls and contemporary artwork enhance the space, while a dining area is visible in the background.

4.93 out of 5 average rating, 206 reviews

Trendy Wicker Park Loft with Parking

Located in trendy Wicker Park, our modern Chicago loft boasts open-plan living, exposed brickwork and plenty of room to accommodate larger groups. Walk down popular North Ave, Milwaukee Ave and Division St. to explore the many shopping, dining, and nightlife options We are centrally located, close to the Blue Line (airport and downtown access) and a block away from the Kennedy (I90/94 expressway).

4.89 out of 5 average rating, 352 reviews

A spacious studio apartment is illuminated by natural light from multiple tall windows. Two queen beds are positioned with cozy linens and decorative pillows, while a wooden dining table with black chairs is seen in the foreground. Wall art and greenery add to the inviting ambiance.

Loft in West Town

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).

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, 254 reviews

Tea Studio in Wicker Park Spring Factory

Welcome to the Tea Studio where you'll create gourmet meals in an immaculate professional grade kitchen. Relax in a one-of-a-kind former spring factory with Chicago's trendiest neighborhood at your doorstep. Sip rare teas and indulge in the sophistication of this Asian-industrial loft. Detox after a long day in a stainless Japanese soaking tub.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Popular amenities for Chicago loft rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly loft rentals

4.81 out of 5 average rating, 144 reviews

A modern kitchen area features dark cabinetry and a marble countertop. Stainless steel appliances, including a refrigerator and oven, are present. A small dining area is situated in the foreground with two black chairs and a wooden stool. A light green wall adds subtle color to the space.

Loft in Near West Side

SPACIOUS and VERY BRIGHT 2BDR LOFT near DOWNTOWN

WendyRating, 5 stars2 weeks ago

We had a girls trip and stayed at this Airbnb and we absolutely loved it! Very clean and it looks better than the photos :) we felt safe inside, it’s spacious, clean and a great deal! If I ever come back with a big group, I’ll consider staying here again.

A cozy bedroom features exposed brick walls and a queen bed, adorned with soft, colorful throw pillows. A small nightstand is positioned beside the bed, adding to the room's functionality. Natural light streams in from a nearby window, creating a warm atmosphere.

Private room in Bridgeport

4.84 out of 5 average rating, 49 reviews

Sunny Spacious Artist Yoga Loft

SeverineRating, 5 stars1 month ago

GuruNischan’s place felt right at home. Friendly, communicative, respectful, both her and her roommate Jose, made my stay a very relaxing experience. The place is clean and quite, I would happily recommend and book again !

Private room in River North

A vibrant rooftop garden is filled with an array of potted plants and flowers, creating a colorful and lush atmosphere. Wooden decking provides a spacious area for relaxation, complemented by seating arrangements. Sunny rays illuminate the scene, enhancing the natural beauty of the garden.

4.88 out of 5 average rating, 958 reviews

Artist Loft, Private Room

FasekaRating, 5 stars3 weeks ago

This is the perfect location for bars and restaurants! It is also in walking distance to public transport which was wonderful! Michael was friendly and helpful! He was in and out of the unit during our stay. The unit is not as clean and organized as pictured but it is beautiful and everything you can expect of an artists loft. Lots of plants, art and collectibles. Would recommend for your next stay in Chicago!

4.75 out of 5 average rating, 65 reviews

Private room in Evanston

Beautiful Space in Evanston Chicago Bungalow

AnnaRating, 5 stars6 months ago

Lovely space for a small family. Nice to be by a park, quiet area and close to major streets as well. Peaceful and nice stay!

4.93 out of 5 average rating, 108 reviews

An open living area is highlighted by large windows allowing natural light. Comfortable seating is arranged around a modern fireplace. The space features wooden beams and a mix of warm and cool colors, with a dining area visible in the background.

Loft in West Town

Urban Glamour in West Town

NickRating, 5 stars1 week ago

Great Airbnb with a responsiveness host and very convenient location. Would definitely stay here again.

Show all

Loft rentals with a washer and dryer

Loft in Pilsen Historic District

A lively exterior of a restaurant is featured, showcasing a black and brick facade adorned with bright signage. The entrance is framed by large glass windows, and the street corner position provides visibility from multiple angles. Decorative light bulbs accentuate the restaurant's name.

4.91 out of 5 average rating, 33 reviews

18th St Cozy and Unique 2BR Loft

TobiasRating, 5 stars2 days ago

A great place for great value. Would definitely come again!

The exterior of a three-story brick building is depicted, featuring ornate architectural details. A prominent bay window showcases large glass panes framed by white detailing, allowing natural light to illuminate the interior. Bright blue skies provide a contrasting backdrop to the structure.

4.94 out of 5 average rating, 18 reviews

City Urban Loft in the Heart of Wicker Park!

NikitaRating, 5 stars2 weeks ago

Everything described and more! Clean, under a 5 min walk to 4 coffee shops, train and bus station and shopping options. Michael was very warm, welcoming and responsive. This Airbnb made a birthday trip to Chicago really special! 🥰

4.87 out of 5 average rating, 110 reviews

An open living space is highlighted by floor-to-ceiling windows, allowing natural light to fill the area. A large sectional sofa in shades of blue and accent chairs in red are arranged around circular tables. Modern artwork adorns the wall, complementing the wooden flooring.

Loft in West Loop

Luxury Fulton Market Penthouse Amazing City Views

AngelaRating, 5 stars1 week ago

Wonderful place to stay for a bachelorette! So much space and overall great location!

4.92 out of 5 average rating, 13 reviews

Loft in Chicago

LUXE Vintage Loft, Home Theatre, 10min to Downtown

BrookeRating, 5 stars2 weeks ago

He was very responsive, great with recommendations. I’m new to air bnb so I needed this. His house was great space nd a lot of great touches for my family

Top guest favorite

The living area showcases a spacious sofa facing a wall-mounted TV and an elegant fireplace. Natural light floods in through large windows, highlighting the vintage tin ceiling. Decorative elements include a wall-mounted American flag and a coffee table situated in the center.

Loft in Logan Square

4.98 out of 5 average rating, 193 reviews

Former Artist Studio

CharlesRating, 5 stars1 week ago

Great apartment, very well situated, well equipped and clean. Friendly welcome by Steve.

4.64 out of 5 average rating, 50 reviews

Loft in Bridgeport

South Loop Luxury Lofts

EulalioRating, 5 stars44 months ago

I planned a small get together of six people to celebrate my best friend’s bachelor weekend. I decided to choose Jose’a Airbnb and I’m glad I did! The place was spacious and it had everything we needed! He had a 55” TV so we can hook up our switch console to play video games. We used the pool table, the dart board, and his poker set! We also cooked up some breakfast at his place too. He had a place to sleep for all six of us and he had towels and pillows/blankets for us to use. We didn’t use the CTA line to go to downtown Chicago but the line was a short walking distance from the Airbnb. I’m glad Jose was comfortable letting us use his Airbnb to celebrate and everything was perfect! Definitely recommend others to use his Airbnb! Thank you Jose!