The widest selection of unusual accommodations in Chicago, IL

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.

Hostel listing. Your accommodation will be based in Chicago.
Facilities and services include an elevator, a room service and a kitchen.

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 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 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 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 three-bedroom Burr Ridge bungalow, near the intersection of I-55, I-294, and I-290, offers easy access to Chicago city centre, approximately 40 kilometres away.
The self-catering property sleeps six guests and boasts a spacious open-plan living and dining area, a fully equipped kitchen with fridge-freezer, microwave, and dishwasher, plus a private pond and fire pit in its large garden.

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 three-bedroom Chicago bungalow, ideally located near O'Hare International Airport and offering easy access to downtown Chicago (approximately 26km from the airport and 20km from the city centre), provides convenient accommodation for travellers.
Sleeping six guests, the self-catering property features a fully equipped kitchen, a private garden with parking, and simple self check-in via lockbox.

This Logan Square dwelling is centrally located in Chicago, offering easy access to attractions such as Michigan Avenue and Millennium Park, though precise distances aren't specified.
This spacious, two-storey loft apartment boasts 278 square metres of living space, featuring five bedrooms, four bathrooms, two kitchens, two living areas, three outdoor spaces and sleeps up to twenty guests; amenities include a sauna, foosball table and record player.