House vacation rentals in Chicago
Find and book unique houses on Airbnb
Top-rated house rentals in Chicago
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago house rentals
House rentals with a pool
Home in Highland Park
4.91 out of 5 average rating, 140 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
Home in New Lenox
4.75 out of 5 average rating, 55 reviewsCheerful home. Heated pool, Hot tub!
Home in Munster
5 out of 5 average rating, 7 reviewsMunster hide away
Home in Near South Side
4.86 out of 5 average rating, 29 reviews2Bed+2Bath PentHouse in South Loop
Home in Bloomingdale
4.94 out of 5 average rating, 34 reviewsGiant Swimming Pool with Whole House!
Home in Bensenville
5 out of 5 average rating, 14 reviewsNew! Arcade+Sauna+Slots+Karaoke+more by O’Hare
Home in Schaumburg
4.82 out of 5 average rating, 11 reviewsSchaumburg Oasis with a Pool and Hidden Garden
Home in Itasca
New place to stayOceanFront Resort Studio at Garza Blanca Cancun MX
Weekly house rentals
Home in Roscoe Village
4.94 out of 5 average rating, 252 reviewsDuplex Home RoscoeVillage/Wrigley Free St Parking
Home in Norwood Park
5 out of 5 average rating, 63 reviewsNo Cleaning Fee Private Apt. Parking Near Airport
Home in Austin
4.88 out of 5 average rating, 104 reviewsUrban Chic 3beds w/2bath + free parking & W/D
Home in Glen Ellyn
4.96 out of 5 average rating, 100 reviews4bd house, Hot-tub, full-basement, pool table&yard
Home in Chicago
4.95 out of 5 average rating, 41 reviewsSpacius unit in historic gem
Home in Chicago Ridge
4.93 out of 5 average rating, 97 reviewsQuiet cul-de-sac with huge fenced in backyard
Home in Irving Park
4.93 out of 5 average rating, 61 reviewsNorthside Chicago Getaway
Home in West Rogers Park
4.9 out of 5 average rating, 51 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
Private house rentals
Home in Logan Square
4.97 out of 5 average rating, 70 reviewsCity Cottage in Logan Square-Avondale
Home in Maywood
4.81 out of 5 average rating, 98 reviewsMaywood Relaxation
Home in Bridgeport
4.86 out of 5 average rating, 100 reviewsFree parking, close to public transit, dining
Home in Skokie
4.88 out of 5 average rating, 90 reviewsA+amazing beauty, entire 2 BR Skokie historic stay
Home in Lincoln Square
4.98 out of 5 average rating, 91 reviewsEntire first floor in Lincoln Square!
Home in Skokie
4.88 out of 5 average rating, 82 reviewsLuxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |
Home in Beverly
4.92 out of 5 average rating, 63 reviewsBeverly House
Home in Gary
4.97 out of 5 average rating, 62 reviewsPrivate 5 Star 2 bedroom modern city farmhouse
Quick stats about house rentals in Chicago
Total rentals
1.9K properties
Total number of reviews
78K reviews
Family-friendly rentals
1K properties are a good fit for families
Pet-friendly rentals
500 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
1.2K properties have a dedicated workspace
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