House holiday 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.
Holiday 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 Schaumburg
Schaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Lincoln Park
Luxury Cabin in Lakeview
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Home in Chicago
2Bed+2Bath PentHouse in South Loop
Home in Carol Stream
Amazing Summer Pool Awaits You!
Home in Olympia Fields
Luxurious South Suburban Villa
Home in Glenwood
Spacious Family Glenwood Estates Home w/ Hot Tub!
Home in West Chicago
Cozy & Specious 1 bedroom lower level Apt
Weekly house rentals
Home in Des Plaines
Urban Farmhouse near O'Hare
Home in Bolingbrook
The Sunshine Spot
Home in North Park
Chicago Riverhouse summer on our patio!
Home in Joliet
The Garden House - Murals and more
Home in Lake View
1-bedroom with full kitchen, washer/dryer inside
Home in Berwyn
Retro Modern Bungalow | free parking | fire pit
Home in Chicago
Boho Chic Coach House 30Min to downtown W/ Parking
Home in Jefferson Park
Chicago getaway for two!
Private house rentals
Home in Munster
Cozy Farmhouse in Munster
Home in Logan Square
City Cottage in Logan Square-Avondale
Home in Garfield Ridge
Chicago Home by Midway near Downtown Attractions
Home in Bridgeport
Cozy, Quiet, Riverwalk Sanctuary
Home in Lincoln Park
Charming 3-BED in Lincoln Park/ Old Town & Parking
Home in Lombard
Modern Boho house in Lombard 7 min to Metra
Home in Oak Park
Cozy & comfy w/free parking & W/D
Home in Norwood Park
3BD Home Mins from Airport | Free Wi-Fi + Parking
Quick stats about house rentals in Chicago
Total rentals
1.8K properties
Rentals with dedicated workspaces
1.2K properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
470 properties allow pets
Family-friendly rentals
950 properties are a good fit for families
Total number of reviews
69K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Earth house rentals United States
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- Rentals with a sauna Chicago
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