The widest selection of unusual accommodations in Chicago, IL

This Chicago bungalow is situated just a short distance from Wrigley Field, in a safe and friendly neighbourhood with plenty of pubs and restaurants nearby. The property has received excellent ratings for its location, cleanliness and overall experience.
The three-bedroom house comfortably sleeps up to nine guests and offers a fully equipped kitchen, a private garden with access until 9pm, and super-fast internet. You’ll also find a separate entrance, a smart lock for easy access, and air conditioning for your comfort.

This three-bedroom Chicago cottage, located in the Bridgeport neighbourhood, offers easy access to public transport (62 bus and subway within 2km) and is a short drive (approx. 8km) from Millennium Park and McCormick Place, with Chinatown a 5-minute drive away.
The single-storey house sleeps six, features a kitchen with fridge, freezer and microwave, air conditioning, a garden, free parking for two cars in a detached garage plus street parking with a permit, and offers step-free access.

This five-bedroom Chicago bungalow is located in the Beverly Hills neighbourhood, a 24km train journey from Chicago's city centre.
Sleeping up to 12 guests, this self-catering house boasts a fully-equipped kitchen, three-and-a-half bathrooms, a games room with pool table and air hockey, private deck, and parking; close to local shops and restaurants.

This penthouse apartment is conveniently located in the centre of Chicago, within easy walking distance of Union Station, Willis Tower, and CIBC Theatre. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment has two bedrooms, comfortably accommodating up to six guests. Enjoy a range of amenities including a rooftop pool, fitness centre, and private parking, as well as a fully equipped kitchen and balcony with stunning city views.

This Berwyn bungalow, situated in a peaceful neighbourhood approximately 32km from downtown Chicago, offers easy access to the city's attractions.
The three-bedroom, one-bathroom house sleeps six guests and boasts a recently remodelled modern interior, including a fully equipped kitchen, air conditioning, free private parking, and all amenities on one floor.

This six-bedroom house is located in a lively neighbourhood, just a short walk from Lake Michigan, Lincoln Park Zoo, Wrigley Field, and the Red Line train. It has received excellent ratings for location, cleanliness, and overall user experience.
This spacious property can comfortably accommodate up to sixteen guests and features a fully equipped kitchen, a private rooftop deck, and a range of entertainment options including a foosball table, vintage slot machine, board games, and a working fireplace.

This charming bungalow is situated in a peaceful neighbourhood just 9.6km from downtown Chicago and 14.5km from the All-State Arena, Rosemont Theater, and Village Park Entertainment District. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The property comprises three bedrooms and one bathroom, comfortably accommodating up to seven guests. Guests can enjoy a range of amenities, including a fully equipped kitchen, free parking, and high-speed internet, making it ideal for both families and groups of friends.

This lakeside Chicago apartment, situated in the downtown area near the Field Museum and Art Institute of Chicago, offers stunning views and easy access to waterfront activities.
The 123-square-metre (1324 sq ft) property boasts three bedrooms, two bathrooms, a fully equipped kitchen, and amenities including a swimming pool, terrace, and on-site fitness centre; nearby options include climbing, biking, and rock climbing.

This Wrightwood neighbourhood three-bedroom house is conveniently located near Healy Metra station, offering easy access to Chicago's city centre (a 24km train journey or 32km drive), O'Hare International Airport, and popular areas such as Lakeview and Wicker Park (both approximately 32km away).
The property boasts a spacious layout sleeping up to nine guests, features a fully equipped kitchen, a large garden with outdoor games and a gas barbecue, plus free on-street and adjacent parking; nearby amenities include Starbucks, Aldi, and Walmart.

This Chicago cabin rental, conveniently located in [Insert Specific Chicago Neighbourhood/Area – e.g., Lincoln Park, a 5km radius from the Magnificent Mile], offers a family-friendly escape.
Sleeping up to four guests in two bedrooms and one bathroom, the lodge provides a fully equipped kitchen (fridge, microwave), air conditioning, parking, internet access, and accepts pets.

This Maywood detached house offers excellent access to Downtown Chicago, situated 17.7 kilometres away and reachable via the 290 expressway or the Blue Line, and is also conveniently located near Brookfield Zoo and The Shops of Downtown Oak Park.
This property boasts a spacious 11,000 sq ft lot with an 11,000-gallon Koi pond, a shaded gazebo with a waterfall, a 'Man Cave' featuring shuffleboard and air hockey, and a state-of-the-art kitchen, accommodating up to 4 guests with 1 bedroom and 1 bathroom.

This Tudor Revival mansion, situated in North Oak Park within walking distance of Oak Park's town centre, offers a unique castle-like experience.
Sleeping up to 16 guests, this four-bedroom, three-bathroom property boasts a performance hall, formal dining room, jacuzzis, four fenced second-floor porches, on-site parking for three vehicles, and event catering equipment (100 chairs, 100 place settings), with additional rooms and beds available on request; all proceeds benefit the Language and Music School's scholarship fund.