House accommodation & holiday rentals in Chicago
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Top-rated house accommodation & 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
4.91 out of 5 average rating, 129 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Schaumburg
5.0 out of 5 average rating, 6 reviewsParadise 4BR w/ Pool & Games
Home in Chicago
4.87 out of 5 average rating, 39 reviewsLuxury Cabin in Lakeview
Home in Glen Ellyn
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
Home in Chicago
4.84 out of 5 average rating, 19 reviews2Bed+2Bath PentHouse in South Loop
Home in Bloomingdale
4.8 out of 5 average rating, 5 reviewsWhole House in Bloomingdale, IL
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Weekly house rentals
Home in Bolingbrook
4.92 out of 5 average rating, 103 reviewsThe Sunshine Spot
Home in Chicago
4.98 out of 5 average rating, 179 reviewsThe Evergreen House
Home in Des Plaines
4.78 out of 5 average rating, 315 reviewsUrban Farmhouse near O'Hare
Home in Chicago
4.92 out of 5 average rating, 115 reviewsSpacious Two Story Luxurious Home w/Outdoor Deck!
Home in Joliet
4.84 out of 5 average rating, 164 reviewsCozy Private Cottage in the Cathedral District
Home in Joliet
4.91 out of 5 average rating, 148 reviewsThe Garden House - Murals and more
Home in Berwyn
4.99 out of 5 average rating, 85 reviewsRetro Modern Bungalow | fire pit | pet friendly
Home in Chicago
4.97 out of 5 average rating, 31 reviewsLakeview Condo
Private house rentals
Home in Chicago
4.98 out of 5 average rating, 52 reviewsCity Cottage in Logan Square-Avondale
Home in Chicago
5.0 out of 5 average rating, 21 reviewsChicago Home by Midway near Downtown Attractions
Home in Munster
5.0 out of 5 average rating, 20 reviewsCozy Farmhouse in Munster
Home in Chicago
4.99 out of 5 average rating, 77 reviewsWhole apartment! 2 Bed/2 bath steps from Wrigley!!
Home in Chicago
4.97 out of 5 average rating, 73 reviewsEntire first floor in Lincoln Square!
Home in Chicago
5.0 out of 5 average rating, 55 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Home in Highland Park
4.93 out of 5 average rating, 41 reviewsWitness Sunrise Over Lake Michigan
Home in Chicago
4.98 out of 5 average rating, 88 reviews3BD 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
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