
House holiday rentals in Chicago
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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 Highland Park
4.92 out of 5 average rating, 142 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*

Home in The Loop
5 out of 5 average rating, 6 reviewsLuxury Condo Downtown Chicago

Home in Munster
5 out of 5 average rating, 10 reviewsMunster hide away

Home in Plainfield
4.81 out of 5 average rating, 36 reviews30 mins to CHI* 3 Kings *Fireplace *W/D* Workspace

Home in Bloomingdale
4.95 out of 5 average rating, 43 reviewsWhole House with a Hot Tub!

Home in Schaumburg
4.87 out of 5 average rating, 15 reviewsSchaumburg Oasis with a Pool and Hidden Garden

Home in Lincoln Park
4.87 out of 5 average rating, 53 reviewsLuxury Cabin in Lakeview

Home in Glenwood
4.8 out of 5 average rating, 55 reviewsSpacious Family Glenwood Estates Home w/ Hot Tub!
Weekly house rentals

Home in Roscoe Village
4.92 out of 5 average rating, 269 reviewsDuplex Home RoscoeVillage/Wrigley Free St Parking

Home in Lansing
4.81 out of 5 average rating, 113 reviewsCozy at the Walter

Home in Avondale
4.86 out of 5 average rating, 221 reviewsThe Avondale Guesthouse

Home in Streamwood
4.98 out of 5 average rating, 47 reviewsSuburban Serenity~Grill, Fire pit, Big yard~

Home in Whiting
4.84 out of 5 average rating, 146 reviewsThe Spa of Downtown Whiting

Home in Lake View
4.95 out of 5 average rating, 182 reviewsWrigleyville Greystone

Home in Justice
4.94 out of 5 average rating, 220 reviews3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin

Home in Worth
4.87 out of 5 average rating, 128 reviews*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Private house rentals

Home in Oak Park
5 out of 5 average rating, 4 reviewsSleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

Home in Chicago
4.94 out of 5 average rating, 16 reviewsWarm bungalow in New City

Home in Logan Square
4.95 out of 5 average rating, 39 reviewsGorgeous and Luxurious 3 BR Home

Home in Austin
4.88 out of 5 average rating, 48 reviewsGrand Victorian Mansion in Austin Area

Home in Blue Island
4.81 out of 5 average rating, 187 reviewsWarm and comfortable inviting Suburban home !

Home in Gary
4.87 out of 5 average rating, 30 reviewsThe Blue House: Family Retreat

Home in Chicago Ridge
4.93 out of 5 average rating, 112 reviewsQuiet cul-de-sac with huge fenced in backyard

Home in Near West Side
4.84 out of 5 average rating, 489 reviews*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN
Quick stats about house rentals in Chicago
Total rentals
2K properties
Total number of reviews
83K reviews
Family-friendly rentals
1.1K properties are a good fit for families
Pet-friendly rentals
520 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
1.3K properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
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- West Side Holiday rentals
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