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 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
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Home in New Lenox
4.74 out of 5 average rating, 34 reviewsCheerful home. Heated pool, Hot tub!
Home in Plainfield
4.89 out of 5 average rating, 27 reviewsPool* King beds* Grill & Patio* 30mi to Chicago
Weekly house rentals
Home in Chicago
4.88 out of 5 average rating, 373 reviewsPro Cleaned & Isolated West Loop Coach House
Home in Chicago
4.82 out of 5 average rating, 115 reviewsExclusive and Spacious Pilsen Guest House
Home in Bolingbrook
4.92 out of 5 average rating, 99 reviewsThe Sunshine Spot
Home in Chicago
4.91 out of 5 average rating, 89 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Berwyn
5.0 out of 5 average rating, 79 reviewsRetro Modern Bungalow | free parking | fire pit
Home in Chicago
4.88 out of 5 average rating, 65 reviewsChicago getaway for two!
Home in Chicago
4.91 out of 5 average rating, 45 reviewsMcFetridge House - Beautiful Private Space #2
Home in Chicago
4.98 out of 5 average rating, 50 reviewsCity Cottage in Logan Square-Avondale
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 16 reviewsChicago Home by Midway near Downtown Attractions
Home in Chicago
5.0 out of 5 average rating, 5 reviews1-bedroom with full kitchen, washer/dryer inside
Home in Chicago
4.89 out of 5 average rating, 28 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
Home in Munster
5.0 out of 5 average rating, 15 reviewsCozy Farmhouse in Munster
Home in Chicago
5.0 out of 5 average rating, 12 reviewsCubby Blue home - Wrigley ~Free Parking~
Home in Chicago
4.96 out of 5 average rating, 28 reviewsLakeview Condo
Home in Chicago
5.0 out of 5 average rating, 49 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Home in Gary
4.98 out of 5 average rating, 40 reviewsPrivate 5 Star 2 bedroom modern city farmhouse
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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