Loft vacation rentals in Cook County

The living area features exposed brick walls and large windows offering natural light. A comfortable couch is positioned near a vintage-style pool table, complemented by a light-colored coffee table and decorative accents. A mounted flat-screen TV and a modern fireplace enhance the inviting ambiance.

4.92 out of 5 average rating, 250 reviews

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.

A vibrant mural adorns the side of a multi-story building, featuring colorful animal faces and abstract designs. The mural creates a striking contrast against the subdued storefronts below, while a nearby boutique displays clothing and accessories in its window, contributing to the lively atmosphere of the street.

4.95 out of 5 average rating, 132 reviews

CT's Art BNB in West Town's Gallery Row

Located in the heart of West Town, this loft-style apartment captures the essence of the Street Art scene in Chicago. Steps away from some of the city's most iconic murals, the interior of this apartment reflects the same vibe with an eclectic collection of original artwork from prolific street artists. This authentic Coach house was completely renovated in Jan 2018. The living room features an Interior Define sleeper sofa that opens up into a queen sized bed (**please request it when booking).

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, 651 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!

4.89 out of 5 average rating, 112 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

An open kitchen and living space is depicted, featuring a mix of modern and rustic elements. A dining table sits beside the kitchen area, complemented by a comfortable couch adorned with cushions. Appliances, including a refrigerator and washer, are visible, emphasizing functionality.

4.78 out of 5 average rating, 561 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)

A bright living area features high ceilings and large windows providing natural light. A striped sofa and a minimalist black chair are positioned around a glass coffee table, complemented by a decorative cowhide rug. Art pieces, including an abstract painting, add character to the space.

4.9 out of 5 average rating, 399 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.

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, 517 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.

4.83 out of 5 average rating, 258 reviews

Loft

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.

4.92 out of 5 average rating, 211 reviews

Trendy Wicker Park Loft with Parking

Discover this spacious Wicker Park loft with soaring timber beam ceilings, where industrial charm meets boutique comfort. Enjoy the convenience of a full size in-unit washer and dryer, ensuite bathroom, and dedicated parking. It’s the perfect retreat to relax and refresh, all while being steps from vibrant dining, nightlife, and quick downtown access. Registration Number: R20000056239

A spacious studio apartment is showcased, featuring light-colored walls and hardwood flooring. Two ceiling fans provide airflow, while a comfortable bed is positioned adjacent to a cozy leather couch. A wooden dining table accommodates several chairs, and framed artwork adorns the walls.

4.9 out of 5 average rating, 358 reviews

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.