
Villa vacation rentals in Chicago
Find and book unique villas on Airbnb
Top-rated villa rentals in Chicago
Guests agree: these villas are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 2 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago villa rentals
Private villa rentals
Superhost

Villa in West Town
New place to stayChic ART|12Guest|3BR|HomeSKYView|Roof|CarGarag|PET
LatashaRating, 5 stars1 month ago
Lovvvvve this place location was great and if u have kids there was a nice trampoline park one block away kids loved it also all the neighbors were very friendly love how the host Natasha left note with some roses, a bottle of wine and some snacks. There is two patio areas that you would love if you were outdoor person. And they also have a rooftop right off the second bedroom and OMG the bathroom in the master bedroom was my favorite the place was clean could have been cleaner but no one is perfect but nothing major you can definitely tell there was animals in the home because my allergies was on a 1000 other than that this place was one of the best places I stayed me and my family loved it and will definitely be back one of the best air bnb/host I have ever stayed with thank u and we left items behind and she asked if she can send them to use I really appreciate that more then she know what yall waiting for please don’t hesitate. This is the perfect spot for you and your family

Villa in South Shore
4.63 out of 5 average rating, 52 reviewsRooftop | Villa | Parking
WosilatRating, 5 stars3 days ago
We had an excellent time here. Our whole dance team was able to stay comfortably and safely. We managed to fit 5 cars in the parking which was essential to us. It was all clean close to everything we came to Chicago for. The communication with the host was great and always prompt. We loved it here.
Superhost

Villa in Westmont
4.8 out of 5 average rating, 45 reviewsWestmont,Il Duplex - Side B. In law suite 1/1
DmytroRating, 5 stars4 months ago
Everything was good. Good place and neighborhood. But I love cooking and the stove was a little bit too small for me.
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- West Side Vacation rentals
- North Side Vacation rentals
- South Bend Vacation rentals
- Lake Michigan Beach Vacation rentals
- Holland Vacation rentals
- South Side Vacation rentals
- South Haven Vacation rentals
- Evanston Vacation rentals
- Saugatuck Vacation rentals
- Loft rentals Chicago
- Waterfront rentals Chicago
- Rentals with an accessible height bed Chicago
- Rentals with beach access Chicago
- Rentals with a home theater Chicago
- Rentals with outdoor seating Chicago
- Rentals with lake access Chicago
- Fitness-friendly rentals Chicago
- Mansion rentals Chicago
- Bed and breakfasts Chicago
- Townhouse rentals Chicago
- Lakehouse rentals Chicago
- Rentals with a patio Chicago
- Rentals with a washer and dryer Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- Rentals with pools Chicago
- Rentals with an EV charger Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- House rentals Chicago
- Rentals with a sauna Chicago
- Rentals with a balcony Chicago
- Apartment rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Smoking-friendly rentals Chicago
- Rentals with a fireplace Chicago
- Kid-friendly rentals Chicago
- Villa rentals Illinois
- Villa rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Six Flags Great America
- 875 North Michigan Avenue
- Lincoln Park Zoo
- Museum of Science and Industry
- The Field Museum
- Wicker Park
- Chicago History Museum
- Willis Tower
- Flossmoor Golf Club
- Brookfield Zoo
- Lincoln Park
- Illinois Beach State Park
- Skokie Country Club
- Garfield Park Conservatory
- Chicago Cultural Center
- Promontory Point
- Things to do Chicago
- Food and drink Chicago
- Wellness Chicago
- Art and culture Chicago
- Sightseeing Chicago
- Entertainment Chicago
- Tours Chicago
- Things to do Cook County
- Tours Cook County
- Wellness Cook County
- Art and culture Cook County
- Food and drink Cook County
- Sightseeing Cook County
- Entertainment Cook County
- Things to do Illinois
- Tours Illinois
- Entertainment Illinois
- Wellness Illinois
- Food and drink Illinois
- Art and culture Illinois
- Sightseeing Illinois
- Things to do United States
- Art and culture United States
- Sports activities United States
- Food and drink United States
- Entertainment United States
- Tours United States
- Sightseeing United States
- Nature and outdoors United States
- Wellness United States