Chicago, IL unique stays

The widest selection of unusual accommodations in Chicago, IL

A cabin, a lighthouse, a glamping, your extraordinary stay awaits you

2 1
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113 Unique places to stay in Chicago, IL

Relax.relate.release In Our Bungalow - Chicago, IL
9.8Excellent 98 reviews
Chicago, IL
8 3
SG$318/nighttotal: SG$954 (3 )

Relax.relate.release In Our Bungalow

bungalow - Chicago
This charming bungalow is situated in a peaceful, tree-lined neighbourhood in the south suburbs of Chicago, just 20 minutes from the city centre and close to major transport links. It consistently receives excellent ratings for cleanliness, location and overall user experience.
The property offers three bedrooms and one bathroom, comfortably accommodating up to eight guests. Amenities include a well-equipped kitchen, air conditioning, a sunny porch, a garden and on-site parking.
Top Floor Of Historic Coachhouse - Chicago, IL
9.7Excellent 132 reviews
Chicago, IL
1 4
SG$519/nighttotal: SG$25431 (49 )

Top Floor Of Historic Coachhouse

apartment - Chicago
This charming apartment is situated in the trendy Bucktown neighbourhood, just a short stroll from the bustling Damen Avenue, known for its vibrant art scene and eclectic shops. It has received excellent ratings for its location, cleanliness, and overall experience.
The flat offers ample space, comfortably sleeping up to 5 guests, and can even accommodate 10 by renting the downstairs unit. Guests can enjoy modern amenities like a fully equipped kitchen, a stylish bathroom, a private garden, and free parking, a rare find in Chicago.
Historic Gem - Oak Park Bungalow - Chicago, IL
9.7Excellent 123 reviews
Chicago, IL
3 3
SG$242/nighttotal: SG$2178 (9 )

Historic Gem - Oak Park Bungalow

apartment - Oak Park
This charming Oak Park bungalow is located just four blocks from the train station, providing easy access to downtown Chicago and major attractions like the United Center and Soldier Field. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The three-bedroom bungalow spans 149 square metres and comfortably accommodates up to six guests. The property features a fully equipped kitchen, a private garden, a spa, and free parking, offering everything you need for a relaxing and enjoyable stay.
Cheerful Haus - Oak Park Area-parking Public Trans - Chicago, IL
9.7Excellent 92 reviews
Chicago, IL
3 2
SG$222/nighttotal: SG$1554 (7 )

Cheerful Haus - Oak Park Area-parking Public Trans

bungalow - Forest Park
This charming bungalow is situated in Forest Park, a short drive from the Chicago Loop and within walking distance of the Blue and Green lines, making it ideal for exploring the city. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The two-bedroom, two-bathroom house comfortably accommodates four guests, offering a spacious and relaxing retreat. It is fully equipped with a kitchen, laundry facilities, and a flat-screen TV, as well as a private garden and a deck, perfect for enjoying the outdoors.
Historic 1920s Bungalow Near Logan Square ! - Chicago, IL
9.8Excellent 107 reviews
Chicago, IL
3 3
SG$733/nighttotal: SG$6597 (9 )

Historic 1920s Bungalow Near Logan Square !

apartment - Chicago
This charming bungalow is located in a quiet historic district in Chicago, just 15-20 minutes from the Lake, Downtown, Wrigley Field, United Center, Oak Park, Soldier Field, and Sox Park. The apartment consistently receives excellent ratings for cleanliness, location, and user experience.
This two-storey home offers 223 square metres of space, including three bedrooms, two bathrooms, and a large walk-in closet. The apartment is family-friendly, with amenities such as a pack-and-play, stroller, highchair, a pull-out bed in the living room, a private backyard with a deck, and a garage for one vehicle.
Prime Location In Heart Of The Windy City - #301 - Chicago, IL
9.5Excellent 243 reviews
Chicago, IL
2 1
SG$301/nighttotal: SG$2107 (7 )

Prime Location In Heart Of The Windy City - #301

studio - Chicago
This studio apartment is conveniently located near the Blue Line L train, providing easy access to both Downtown Chicago and the vibrant West Loop neighbourhood with its abundance of restaurants, bars, and shops. It has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
This self-catering apartment can accommodate up to three guests and features a modern kitchen, in-unit laundry, and spa baths. It also includes parking, internet access, and air conditioning, ensuring a comfortable and convenient stay.
Handicap Accessible! Comfortable & Unique - #102 - Chicago, IL
9.5Excellent 62 reviews
Chicago, IL
1 1
SG$253/nighttotal: SG$12397 (49 )

Handicap Accessible! Comfortable & Unique - #102

studio - Chicago
This studio apartment is conveniently located in Chicago, close to the Blue Line L, providing easy access to both downtown and the West Loop's vibrant restaurant scene. The studio has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment is ideal for solo travellers and features a modern kitchen with a fridge and microwave, as well as a washer and dryer for added convenience. Amenities include air conditioning, parking, and internet access, along with spa baths for a touch of luxury.
Cabin 103 At 747 Lofts - Chicago, IL
9.5Excellent 106 reviews
Chicago, IL
1 1
SG$266/nighttotal: SG$13034 (49 )

Cabin 103 At 747 Lofts

studio - Chicago
This studio apartment is ideally situated near the Blue Line L in Chicago, providing easy access to both the city centre and the trendy West Loop, home to Randolph Street's renowned restaurant scene. The studio has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment comfortably accommodates one guest and features a modern kitchen with a fridge and microwave. Amenities include air conditioning, parking, internet access, and a laundry facility, ensuring a comfortable and convenient stay.
Cabin 101 At 747 Lofts - Chicago, IL
9.6Excellent 76 reviews
Chicago, IL
3 1
SG$401/nighttotal: SG$3609 (9 )

Cabin 101 At 747 Lofts

studio - Chicago
This studio apartment is conveniently located near the Blue Line L, offering easy access to downtown Chicago and the bustling West Loop neighbourhood. The property has received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The studio is ideal for a group of up to three guests and features a modern kitchen, a bathroom with a spa bath, and in-unit laundry facilities. Guests can enjoy convenient access to local amenities, including restaurants, bars, and shops, all within walking distance.
Ada Accessible! Handicap-friendly - #106 - Chicago, IL
9.5Excellent 85 reviews
Chicago, IL
1 1
SG$245/nighttotal: SG$12005 (49 )

Ada Accessible! Handicap-friendly - #106

studio - Chicago
This studio apartment is situated in a prime location in Chicago, just a short stroll from the West Loop and Randolph Street's renowned restaurant scene, offering easy access to downtown via the Blue Line L. The apartment consistently receives excellent ratings for location, cleanliness, and overall guest experience.
The self-catering studio comfortably accommodates two guests and features a modern kitchen with a fridge and microwave, as well as a laundry facility. Amenities include air conditioning, parking, and 24/7 customer support, ensuring a comfortable and convenient stay.
Nice Bungalow In Quiet Area - Chicago, IL
10Excellent 3 reviews
Chicago, IL
1 2
SG$130/nighttotal: SG$6370 (49 )

Nice Bungalow In Quiet Area

house - Melrose Park
This Melrose Park house is conveniently located just 3 miles from Dominican University and within 6 miles of several other universities, medical facilities, and historical landmarks, making it a great base for exploring the area. The property has received excellent ratings for location, cleanliness, and user experience.
This two-bedroom home can comfortably accommodate up to four guests and features a fully equipped kitchen, laundry facilities, and free Wi-Fi. The house is also situated in a quiet neighbourhood, offering a peaceful retreat after a day of exploring the city.
Spacious Townhome! 3 Bedrooms & 2 Complete Bath And 2 Outdoor Patios, Near Train - Chicago, IL
10Excellent 29 reviews
Chicago, IL
3 3
SG$694/nighttotal: SG$6246 (9 )

Spacious Townhome! 3 Bedrooms & 2 Complete Bath And 2 Outdoor Patios, Near Train

train - Chicago
This train is situated in Lincoln Park, Chicago, a 10-minute train ride from Millennium Park and the city centre. It has received excellent ratings from previous guests. This comfortable property has three bedrooms and two bathrooms, sleeping up to six guests. You can enjoy amenities like a Jacuzzi, a terrace, and a garden, as well as parking, internet, and a fully equipped kitchen.

Other types of accommodation in Chicago, IL

Best Chicago, IL unique stays with a jacuzzi

Among the 113 accommodations in Chicago, IL, here are the 2 best unique accommodations with a jacuzzi

Gorgeous Historic Mansion On Uchicago Campus. Renovation With Original Detail. - Chicago, IL
Chicago, IL
2 5
SG$1020/nighttotal: SG$6120 (6 )

Gorgeous Historic Mansion On Uchicago Campus. Renovation With Original Detail.

manor house - Chicago
This manor house is situated in Hyde Park, a short walk from notable landmarks like 4944 S Woodlawn Ave and Robie House, offering a peaceful retreat close to Lake Michigan and Grant Park. The accommodation is perfect for families or groups of up to seven guests, with five bedrooms and five bathrooms.
The manor house provides modern comforts such as Wi-Fi, a smart TV, and air conditioning, as well as a well-equipped kitchen for preparing meals. Enjoy outdoor relaxation with a barbecue area and a hot tub, making it an ideal choice for exploring Chicago.
Family Friendly 5b\/ 4ba Sun-drenched Home In Jefferson Park, 2 Car Garage! - Chicago, IL
Chicago, IL
8 5
SG$1499/nighttotal: SG$4497 (3 )

Family Friendly 5b\/ 4ba Sun-drenched Home In Jefferson Park, 2 Car Garage!

car - Chicago
This comfortable home is located in the peaceful Jefferson Park neighbourhood, a short walk from Milwaukee Avenue and a 10-minute walk from the Jefferson Park train station. The property is ideal for families or groups, offering five bedrooms and four bathrooms, comfortably accommodating up to 11 guests. The home is well-equipped with modern amenities, including air conditioning, Wi-Fi, a smart TV, a fully equipped kitchen, and a washer and dryer, ensuring a comfortable and enjoyable stay.

Best family friendly Chicago, IL unique stays

Among the 113 accommodations in Chicago, IL, here are the 6 best family friendly unique accommodations

Beautiful 4 Bedroom 3 Full Bath Bungalow - Chicago, IL
9.9Excellent 55 reviews
Chicago, IL
3 4
SG$429/nighttotal: SG$3861 (9 )

Beautiful 4 Bedroom 3 Full Bath Bungalow

apartment - Berwyn
This spacious four-bedroom flat is located in Berwyn, just west of Chicago, making it a convenient base for exploring the city and surrounding areas. It has consistently received excellent reviews from previous guests for its cleanliness, location, and overall experience.
The 167 square metre flat comfortably accommodates up to eight guests, offering a fully equipped kitchen, a private garden, a fitness centre, and parking for multiple vehicles. The property boasts a range of amenities to ensure a comfortable and enjoyable stay, including a dedicated play area, a basement living space, and a quiet and relaxing atmosphere.
Historic Chicago Bungalow ~ 12 Mi To Downtown - Chicago, IL
Chicago, IL
1 3
SG$210/nighttotal: SG$10290 (49 )

Historic Chicago Bungalow ~ 12 Mi To Downtown

bungalow - Chicago
This charming house is located in Elmwood Park, a quiet neighbourhood just outside Chicago, a short drive from popular attractions like Wrigley Field and Navy Pier. The property is also close to the Garfield Park Conservatory, a beautiful green space perfect for a relaxing stroll.
This three-bedroom house can comfortably sleep six guests and spans 279 square metres. Enjoy modern comforts like a fully equipped kitchen, Smart TVs, a fireplace, and a movie room with a 60-inch Smart TV and soundbar, as well as a secure garage for one vehicle.
Oak Park, Il, Entire House, Short Walk To Train. - Chicago, IL
9.1Excellent 16 reviews
Chicago, IL
2 3
SG$453/nighttotal: SG$14043 (31 )

Oak Park, Il, Entire House, Short Walk To Train.

train - Chicago
This train is located in Oak Park, a suburb of Chicago, just minutes from the expressway, train station, and downtown Chicago. It has received excellent user ratings, making it a popular choice for travellers.
The train offers three bedrooms, one bathroom, and a floor area of 112 square metres, accommodating up to eight guests. It includes amenities such as a kitchen with a fridge and microwave, air conditioning, a garden, parking, and internet access.
Lux Chicago Home-  6 Bd 4 Ba- 2 Car Garage.  25 Mins To Downtown. - Chicago, IL
10Excellent 1 review
Chicago, IL
2 6
SG$976/nighttotal: SG$5856 (6 )

Lux Chicago Home- 6 Bd 4 Ba- 2 Car Garage. 25 Mins To Downtown.

car - Chicago
This car is located in Belmont Cragin, a neighbourhood in Chicago, around 10 miles from downtown attractions like Navy Pier and Michigan Avenue. It's an area with a rich cultural heritage, offering a unique experience for visitors. The car has excellent user ratings, ensuring a comfortable and enjoyable stay.
This car has six bedrooms and four bathrooms, offering spacious accommodation for up to two guests. It comes with a kitchen featuring a fridge, microwave oven, and dishwasher, a terrace, parking, and internet access.
La Quinta By Wyndham Chicago O'hare Airport - Chicago, IL
8.0Very good 54 reviews
Chicago, IL
8 6
SG$1179/nighttotal: SG$3537 (3 )

La Quinta By Wyndham Chicago O'hare Airport

farm - Rosemont
This hotel, La Quinta by Wyndham Chicago O'Hare Airport, is located in Rosemont, Illinois, a short distance from Allstate Arena and a 2-minute drive from Lake Park. It has received very good ratings for cleanliness, location, and overall experience. The accommodation offers a range of amenities, including a fitness centre, complimentary Wi-Fi, a business centre, and a 24-hour front desk. Guests can also enjoy a complimentary buffet breakfast, a television in a common area, and other features like gift shops and vending machines.
Huge & Luxurious Logan Sq Home,2 Car Garage,private Rooftop Deck,great Location! - Chicago, IL
Chicago, IL
2 5
SG$1798/nighttotal: SG$10788 (6 )

Huge & Luxurious Logan Sq Home,2 Car Garage,private Rooftop Deck,great Location!

car - Chicago
This spacious home is situated in Logan Square, a lively neighbourhood on Chicago's northwest side, within easy reach of Lake Michigan, Millennium Park, and Wrigley Field. The property offers five bedrooms, four bathrooms, and can comfortably accommodate up to 12 guests across its 279 square metres.
The property features a private rooftop deck, a well-equipped kitchen, high-speed internet, and a two-car garage, making it ideal for families or groups looking for a comfortable and convenient base for exploring the city.

Destinations nearby

Best pet friendly Chicago, IL unique stays

Among the 113 accommodations in Chicago, IL, here are the 8 best pet friendly unique accommodations

4 Spacious Units Close To Navy Pier And Willis Tower! Parking, Pets Allowed! - Chicago, IL
Chicago, IL
4 4
SG$1572/nighttotal: SG$4716 (3 )

4 Spacious Units Close To Navy Pier And Willis Tower! Parking, Pets Allowed!

tower - Chicago
This tower is situated in Downtown Chicago, just a short walk from Millennium Park and Lake Michigan, offering easy access to the city's cultural attractions and vibrant waterfront.
The Deluxe Two Double accommodation provides 377 square feet of space, comfortably sleeping up to 16 guests, and includes a dedicated sitting area, a flat-screen TV, and a minibar. Guests can enjoy a range of amenities, including a fitness centre, a business centre, and on-site parking.
Cabin 105 By 747 Lofts - Chicago, IL
10Excellent 1 review
Chicago, IL
2 1
SG$446/nighttotal: SG$13826 (31 )

Cabin 105 By 747 Lofts

cabin - Chicago
This studio apartment is located in the West Town neighbourhood of Chicago, a short walk from the Blue Line L train and the lively Randolph Street restaurant scene. It has been rated excellent by previous guests.
This comfortable apartment is suitable for two guests and has a modern and stylish interior design. Amenities include a fully equipped kitchen, in-unit laundry, and a spa bath.
Vacation Day Is Always A Great Idea! Near Water Tower Chicago, Pet-friendly - Chicago, IL
Chicago, IL
3 1
SG$2054/nighttotal: SG$14378 (7 )

Vacation Day Is Always A Great Idea! Near Water Tower Chicago, Pet-friendly

tower - Chicago
This tower is conveniently located in Chicago's city centre, just a short walk from Navy Pier, Michigan Avenue, Millennium Park, and Grant Park. The surrounding area is bustling with activity and offers a range of restaurants, shops, and attractions.
The tower offers one-bedroom apartments, each with a floor area of 51 square metres and a capacity of three guests. Guests can enjoy a range of amenities, including a fitness centre, restaurant, bar, terrace, and complimentary bicycles.
Always A Great Idea To Unwind! Short Drive To Water Tower Chicago! - Chicago, IL
Chicago, IL
2 1
SG$449/nighttotal: SG$898 (2 )

Always A Great Idea To Unwind! Short Drive To Water Tower Chicago!

tower - Chicago
This tower is located in downtown Chicago, just a short walk from Michigan Avenue, Navy Pier, Grant Park, and Millennium Park. The area is lively and offers easy access to many of the city's most popular attractions.
The tower offers comfortable and spacious accommodation with a floor area of 37 square metres, perfect for a couple. It features a range of amenities, including a fitness centre, swimming pool, restaurant, bar, business centre, mini market, laundry facilities, and a ballroom, making it a great choice for families and business travellers alike.
A Place You''ll Surely Enjoy! Short Drive To Water Tower Chicago & Willis Tower! - Chicago, IL
Chicago, IL
2 1
SG$505/nighttotal: SG$3535 (7 )

A Place You''ll Surely Enjoy! Short Drive To Water Tower Chicago & Willis Tower!

tower - Chicago
This tower is situated in the heart of downtown Chicago, just a short walk from Michigan Avenue, Navy Pier, Millennium Park, and Lake Michigan, offering easy access to the city's main attractions. Each apartment has a floor area of 28 square metres and can comfortably accommodate two guests.
The tower provides a range of amenities, including a fitness centre, a pool, a restaurant and bar, and a business centre, as well as daily housekeeping and valet parking. Guests can also enjoy a variety of on-site activities, such as kayaking and sailing, or explore the many attractions and events that Chicago has to offer.
Conveniently To Excellent Transportation! 2 Spacious Units, Near Willis Tower - Chicago, IL
Chicago, IL
3 2
SG$879/nighttotal: SG$6153 (7 )

Conveniently To Excellent Transportation! 2 Spacious Units, Near Willis Tower

tower - Chicago
This tower is conveniently located in Chicago's city centre, just a short distance from Michigan Avenue, Navy Pier, Millennium Park, and Lake Michigan. The surrounding area offers a vibrant mix of shopping, entertainment, and cultural attractions.
The tower has two units, each with a floor area of 74 square metres, comfortably accommodating up to 10 guests. The tower offers a range of amenities, including a fitness centre, swimming pool, restaurant, bar, business centre, mini market, library, laundry facilities, and a ballroom.
Picasso Statue Tour! 2 Relaxing Units Near Art Institute Of Chicago - Chicago, IL
Chicago, IL
2 2
SG$1266/nighttotal: SG$30384 (24 )

Picasso Statue Tour! 2 Relaxing Units Near Art Institute Of Chicago

tower - Chicago
This tower is conveniently located in the heart of Chicago, just a short walk from Michigan Avenue, Navy Pier, Grant Park, and Millennium Park. The surrounding area is bustling with activity, offering a vibrant mix of shops, restaurants, and entertainment venues.
The tower offers comfortable accommodation with two bedrooms and two bathrooms, providing ample space for up to eight guests. It features a range of amenities, including a fitness centre, a pool, a restaurant, and a business centre, ensuring a comfortable and enjoyable stay.
Vacation At Its Finest! 3 Family-friendly Units, Minutes To Water Tower Chicago - Chicago, IL
Chicago, IL
3 3
SG$1115/nighttotal: SG$7805 (7 )

Vacation At Its Finest! 3 Family-friendly Units, Minutes To Water Tower Chicago

tower - Chicago
This tower is situated in the heart of Chicago, just a short walk from Michigan Avenue and Navy Pier, offering easy access to Grant Park and Millennium Park. The surrounding area is bustling with activity, offering a vibrant mix of shops, restaurants, and cultural attractions.
This three-bedroom, three-bathroom apartment offers 111 square metres of space and can comfortably accommodate up to 15 guests. The tower provides a range of amenities including a fitness centre, swimming pool, restaurant, bar, business centre, mini market, library, laundry facilities, ballroom, and valet parking.

Neighborhoods and points of interest in Chicago, IL