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 house rentals in Chicago
House rentals with a pool
Home in Highland Park
4.9 out of 5 average rating, 126 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
Home in Plainfield
4.95 out of 5 average rating, 63 reviewsLarge Spanish style Home (w/heated pool)
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, 3 reviewsParadise 4BR w/ Pool & Games
Home in Chicago
4.87 out of 5 average rating, 38 reviewsLuxury Cabin in Lakeview
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Weekly house rentals
Home in Chicago
4.95 out of 5 average rating, 131 reviewsChicago Riverhouse summer on our patio!
Home in Bolingbrook
4.92 out of 5 average rating, 100 reviewsThe Sunshine Spot
Home in Chicago
4.8 out of 5 average rating, 117 reviewsExclusive and Spacious Pilsen Guest House
Home in Chicago
4.98 out of 5 average rating, 175 reviewsThe Evergreen House
Home in Chicago
4.91 out of 5 average rating, 90 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Berwyn
4.99 out of 5 average rating, 84 reviewsRetro Modern Bungalow | free parking | fire pit
Home in Chicago
4.86 out of 5 average rating, 69 reviewsChicago getaway for two!
Home in Wilmette
4.98 out of 5 average rating, 96 reviewsUnique porcelain-enamel paneled "Lustron" home
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 18 reviewsChicago Home by Midway near Downtown Attractions
Home in Chicago
5.0 out of 5 average rating, 52 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Home in Gary
4.95 out of 5 average rating, 43 reviewsPrivate 5 Star 2 bedroom modern city farmhouse
Home in Chicago
4.97 out of 5 average rating, 32 reviewsLight and bright 3BD duplex in Avondale, Chicago
Home in Chicago
5.0 out of 5 average rating, 12 reviewsCubby Blue home - Wrigley ~Free Parking~
Home in Chicago
4.98 out of 5 average rating, 88 reviews3BD Home Mins from Airport | Free Wi-Fi + Parking
Home in Munster
5.0 out of 5 average rating, 17 reviewsCozy Farmhouse in Munster
Home in Oak Park
4.96 out of 5 average rating, 77 reviewsClean, Cozy Duplex with Kitchen & Free 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
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