Find & Compare Unique Stays in Chicago

Experience a unique stay in this compact cabin, located in a Chicago district where the sole bathroom is accessed through the master bedroom.
This family-friendly cabin accommodates two guests with a fridge, microwave, and air conditioning for a comfortable and unusual accommodation.

Just 500 feet from the South Shore Train line, this bungalow offers a unique stay in Chicago's South Shore, providing a 15-20 minute commute to Soldier Field and Millennium Park.
This 2-bedroom bungalow accommodates up to 3 guests with a full kitchen and a large yard, making it an unusual accommodation for exploring the city.

Discover a unique stay in this Chicago bungalow, just 4 miles from O'Hare Airport and offering easy access to downtown attractions.
This bungalow provides a fenced backyard and a well-equipped kitchen, perfect for up to 6 guests seeking an unusual accommodation.

Located in the quiet Wrightwood Neighborhood Greenway, this updated bungalow is a 5-minute walk from the Metra Healy Station for a 15-minute commute downtown.
This bungalow offers a unique stay with a spacious backyard, memory foam beds, and a 70" smart TV, perfect for a memorable trip.

Discover a unique stay in North Oak Park, a short walk from downtown Oak Park's shops and cultural venues.
This historic Tudor Revival castle offers 4 bedrooms, 3 bathrooms, and accommodates 16 guests with optional kitchen and third-floor access for an unusual accommodation experience.

Located in Chicago's upscale Beverly Hills neighborhood, this bungalow offers a unique stay just a 15-minute Metra train ride from downtown attractions.
This bungalow boasts a fully finished basement entertainment hub with air hockey, a pool table, and video gaming, providing an unusual accommodation experience for up to 12 guests.

Located in Chicago's Jefferson Park neighborhood, this bungalow is a 20-minute walk from recreational facilities including a park and pools.
Enjoy a professionally designed interior with vintage style and a private balcony at this unique stay, offering a one-of-a-kind stay for up to four guests.

Just 0.5 miles from Wrigley Field, this Chicago bungalow offers a unique stay in a safe neighborhood.
This family-friendly bungalow accommodates up to 9 guests, featuring a full kitchen, a king master suite with a private bath, and backyard access for an unusual accommodation experience.

Conveniently located just 14 miles from O'Hare Airport and 18 miles from downtown Chicago, this bungalow offers a prime base for exploring Rosemont's attractions and Allstate Arena.
This family-friendly bungalow provides a unique stay with 3 bedrooms, 1 bathroom, and a full kitchen, perfect for up to 6 guests seeking an unusual accommodation.

Just blocks from Lake Michigan, Lincoln Park Zoo, and Wrigley Field, this bungalow offers a unique stay with a Prohibition-era bootlegger's past and an escape door.
This spacious 3,500+ sq ft home sleeps 16 and features a rooftop deck, foosball, a vintage slot machine, and private parking.

Nestled in Berwyn, this recently remodeled bungalow offers a tranquil suburban escape just a 20-mile drive from downtown Chicago.
This bungalow provides a unique stay for up to six guests, featuring a modern kitchen and air conditioning for comfort.

Located in Maywood, this bungalow is 11 miles from Downtown Chicago, with easy access to the 290 expressway and Blue Line.
Discover a unique stay with a 4,500-gallon Koi pond, waterfall, and a 'Man Cave' featuring shuffleboard and air hockey.