The widest selection of unusual accommodations in Chicago, IL

This farm is located in the countryside of Rosemont, 5 kilometers from the town center and 8 kilometers from Rosemont Castle.
Guests can enjoy the authentic farm atmosphere, explore scenic walking trails, and benefit from spacious grounds and comfortable lodging.

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.

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 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 historic 1905 Revival Tudor-style mansion, designed by Henry Fiddelke, is located in Oak Park, 322 metres from Frank Lloyd Wright's Home and Studio and the Hemingway Museum.
This private guest room within the grand residence accommodates two guests and features a Jacuzzi and a piano, with proceeds from separate event rentals supporting The Language and Music School’s scholarship fund.

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 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 accommodation is located in Chicago's Loop district, just 200 meters from Millennium Park and the Art Institute of Chicago, offering convenient access to the Magnificent Mile.
This tower provides modern interiors, stunning city and lake views, and on-site parking, with excellent public transport links for exploring the city.

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 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.