Search unique places to stay in Chicago from 100+ sites!

This Tudor Revival mansion, located in North Oak Park within walking distance of downtown Oak Park's shops and restaurants, offers a unique castle-like experience. This Oak Park castle boasts four bedrooms, three bathrooms, two Jacuzzis, and can accommodate up to 16 guests, featuring a large performance hall (permit required), outdoor parking for three cars, and amenities for events including 100 chairs and cutlery.

This three-bedroom, one-bathroom Chicago cottage is located in the quiet Bridgeport neighborhood, a short walk from the 62 bus and subway lines and a short drive from Chinatown, Millennium Park, and McCormick Place.
The single-story house, offering free parking in a two-car garage plus street parking with a permit, comfortably sleeps six guests and features a fully equipped kitchen (fridge, freezer, microwave), air conditioning, a garden, and step-free access.

This Burr Ridge bungalow, near I-55, I-294, and I-290, offers easy access to downtown Chicago, approximately 25 minutes away without traffic.
This three-bedroom, one-bathroom house comfortably sleeps six guests and features a fully equipped kitchen, a private pond, and a luxurious backyard with a fire pit.

This Chicago bungalow, located in the Wrightwood neighborhood, offers easy access to the Healy Metra station (5-minute drive) for a quick 15-minute train ride downtown, and is within 20 minutes of Lakeview, Wrigleyville, and O'Hare International Airport.
The three-bedroom, one-bathroom house sleeps nine guests and features a large living room with a 70" smart TV, a well-equipped kitchen, a spacious backyard with a gas grill, and is close to Kelvin Park, Starbucks, Aldi, and Walmart.

This three-bedroom Chicago bungalow near O'Hare International Airport offers easy access to both the airport and downtown attractions.
The 3-bathroom home comfortably sleeps six guests and features a fully equipped kitchen, fenced backyard, and on-site parking.

This historic bungalow in Chicago's Lakeview neighborhood offers a unique stay for travelers seeking a spacious and entertaining vacation rental. With excellent user and location ratings, this 6-bedroom, 2-bathroom property can accommodate up to 16 guests.
The bungalow features a private rooftop deck, a foosball table, a vintage slot machine, multiple 85-inch TVs, and a fully equipped kitchen. It also has a large dining area, comfortable furnishings, and a working fireplace, making it a perfect place for families and groups to relax and enjoy their stay in Chicago.

This Maywood bungalow offers prime access to Downtown Chicago, 11 miles via I-290 or the Blue Line, and is conveniently located near Brookfield Zoo and The Shops of Downtown Oak Park.
This 1-bedroom, 1-bathroom dwelling accommodates up to 4 guests and features a state-of-the-art kitchen, air conditioning, a garden with a Koi pond and waterfall, and a unique 'Man Cave' with shuffleboard and air hockey.

This Beverly Hills, Chicago bungalow is conveniently located a 15-minute train ride from downtown Chicago, offering easy access to the city's attractions.
Sleeping up to 12 guests, this five-bedroom, 3.5-bathroom home boasts a fully finished basement with a pool table, air hockey, and video games, plus a private deck and enclosed porch.

This Chicago home is located in a safe and family-friendly neighborhood, just a short distance from pubs, restaurants, and Wrigley Field. It consistently receives excellent ratings for location, cleanliness, and user experience. This comfortable bungalow features three bedrooms and two bathrooms, comfortably sleeping up to nine guests. Amenities include a fully equipped kitchen, a private backyard, fast internet, and air conditioning, making it perfect for families or groups of friends exploring Chicago.

Hostel. You will be in Chicago.
Services and facilities: a room service, a kitchen and an elevator.

This Chicago home is located in a safe and family-friendly neighborhood, just a short distance from pubs, restaurants, and Wrigley Field. It consistently receives excellent ratings for location, cleanliness, and user experience. This comfortable bungalow features three bedrooms and two bathrooms, comfortably sleeping up to nine guests. Amenities include a fully equipped kitchen, a private backyard, fast internet, and air conditioning, making it perfect for families or groups of friends exploring Chicago.

This historic bungalow in Chicago's Lakeview neighborhood offers a unique stay for travelers seeking a spacious and entertaining vacation rental. With excellent user and location ratings, this 6-bedroom, 2-bathroom property can accommodate up to 16 guests.
The bungalow features a private rooftop deck, a foosball table, a vintage slot machine, multiple 85-inch TVs, and a fully equipped kitchen. It also has a large dining area, comfortable furnishings, and a working fireplace, making it a perfect place for families and groups to relax and enjoy their stay in Chicago.

This Tudor Revival mansion, located in North Oak Park within walking distance of downtown Oak Park's shops and restaurants, offers a unique castle-like experience. This Oak Park castle boasts four bedrooms, three bathrooms, two Jacuzzis, and can accommodate up to 16 guests, featuring a large performance hall (permit required), outdoor parking for three cars, and amenities for events including 100 chairs and cutlery.

This Burr Ridge bungalow, near I-55, I-294, and I-290, offers easy access to downtown Chicago, approximately 25 minutes away without traffic.
This three-bedroom, one-bathroom house comfortably sleeps six guests and features a fully equipped kitchen, a private pond, and a luxurious backyard with a fire pit.

This historic bungalow in Chicago's Lakeview neighborhood offers a unique stay for travelers seeking a spacious and entertaining vacation rental. With excellent user and location ratings, this 6-bedroom, 2-bathroom property can accommodate up to 16 guests.
The bungalow features a private rooftop deck, a foosball table, a vintage slot machine, multiple 85-inch TVs, and a fully equipped kitchen. It also has a large dining area, comfortable furnishings, and a working fireplace, making it a perfect place for families and groups to relax and enjoy their stay in Chicago.

This Chicago bungalow, located in the Wrightwood neighborhood, offers easy access to the Healy Metra station (5-minute drive) for a quick 15-minute train ride downtown, and is within 20 minutes of Lakeview, Wrigleyville, and O'Hare International Airport.
The three-bedroom, one-bathroom house sleeps nine guests and features a large living room with a 70" smart TV, a well-equipped kitchen, a spacious backyard with a gas grill, and is close to Kelvin Park, Starbucks, Aldi, and Walmart.