The 10 best villas in Chicago, USA | Booking.com
Skip to main content

Villas in Chicago

Find the villas that appeal to you the most

The best villas in Chicago

Check out our pick of great villas in Chicago

Show all

Looking for a villa?

Perfect for families, groups or couples who enjoy luxury and independence while travelling. Enjoy the space and privacy of these fully-furnished, self-standing mansions — travellers can cook, lounge and explore at their leisure. Note that in Bali, a resort will also be called a villa.

Most booked villas in Chicago and surroundings in the past month

See all

Travelling by car? These villas in Chicago and nearby offer free parking

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 7 reviews

    Right in the centre of Chicago, situated within a short distance of Oak Street Beach and 360 Chicago, Historic luxury Townhouse in Downtown Chicago offers free WiFi, air conditioning and household...

  • Spacious 3-Bed West Loop Townhouse, 1 Car Garage is located in the West Loop district of Chicago, 2.2 km from CIBC Theatre, 2.4 km from United Center and 2.4 km from Depaul University.

  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 5 reviews

    Right in the heart of Chicago, Luxurious Gold Coast 4BR 4-Story Villa with Parking Sleeps 12 Guests has garden views from the balcony.

  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 5 reviews

    Boasting a patio with city views, a garden and barbecue facilities, 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome can be found in Chicago, close to Oak Street Beach and 2.2...

  • Located in Chicago, this holiday home is 1.1 km from Lincoln Park Zoo and Downtown Chicago. Offering free private parking, the holiday home is 1.5 km from 360 Chicago.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 1 review

    Old Town 3bd 3ba Coach House, Garage Parking Incl is situated in the Old Town district of Chicago, 2.6 km from 360 Chicago, 2.7 km from Chicago Museum of Contemporary Art and 3.3 km from Lincoln Park...

  • Wicker Park 6bd 4ba, Steps from CTA, Parking Incl home is set in the Wicker Park district of Chicago, 4.3 km from Union Station, 4.5 km from 360 Chicago and 4.5 km from Chicago Museum of Contemporary...

  • Wicker Park 4bd 3ba, Steps from CTA, Parking Incl home is located in the Wicker Park district of Chicago, 4.3 km from Union Station, 4.5 km from 360 Chicago and 4.5 km from Chicago Museum of...

Enjoy breakfast in Chicago and nearby

Great access to the city centre. Check these villas in Chicago and nearby

  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 3 reviews

    Offering a garden and garden view, Perfect Location Across from Park & Train Station is located in Chicago, 8.3 km from CIBC Theatre and 8.8 km from Shops at Northbridge.

  • Situated in Chicago, 1.1 km from Wrigley Field and 5.5 km from Lincoln Park Zoo, Wrigley 4BR Home, Sleeps 10 provides accommodation with amenities such as free WiFi and a flat-screen TV.

  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 14 reviews

    Located in Chicago in the Illinois region, Spacious 5-BR House near Transit w Parking features a balcony. This property offers access to a terrace, free private parking and free WiFi.

  • 2 Mi to Red Line Chicago Home Near Sherman Park is situated in Chicago, 5.8 km from Guaranteed Rate Field, 7 km from Museum of Science and Industry - Chicago, and 11 km from Union Station.

  • Located in Chicago, 5.2 km from Wrigley Field and 8.1 km from Lincoln Park Zoo, Chicago Chic, Cozy 1BR with Stylish Workspace offers air conditioning.

  • Located in Chicago, 5.2 km from Wrigley Field and 8.1 km from Lincoln Park Zoo, Chicago 1BR, Stylish Stay with Workspace offers air conditioning.

  • Situated in Chicago, 5.2 km from Wrigley Field and 8.1 km from Lincoln Park Zoo, Huge Projector and Designated Workspace, Near Wrigley offers air conditioning.

  • Located in Chicago, 5.2 km from Wrigley Field and 8.1 km from Lincoln Park Zoo, Fitness Pad, Stylish 2BR with Gym in Chicago offers air conditioning.

FAQ about villas in Chicago

Research, refine and make plans for your whole trip

Villas in Illinois

Widen your search and check out the best villas in the surrounding area.

Hotels near Naval Training Center, Great Lakes

Hotels close to a popular local landmark.

Hotels near Allstate Arena

Hotels close to a popular local landmark.

Flights to Midway International Airport

Jet into this airport to explore Chicago at your leisure.

Flights to Chicago O'Hare International Airport

Jet into this airport to explore Chicago at your leisure.

Villas in Evanston

Find more hotels in a city close to Evanston.

Villas in Rosemont

Flexible on where to stay? Look up villas in nearby Rosemont, not too far from Chicago.

Hotels in Chicago

More great accommodation options for your trip.

Cheap hotels in Chicago

More great accommodation options for your trip.