Vacation rentals in Chicago
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Top-rated vacation rentals in Chicago
Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Chicago vacation rentals
Other great vacation rentals in Chicago
Apartment in Cicero
4.98 out of 5 average rating, 201 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Mar. 21 – 28
Guest suite in Chicago
4.96 out of 5 average rating, 319 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
Feb. 13 – 20
Loft in Wicker Park
4.78 out of 5 average rating, 482 reviewsWicker Park Loft - Walk To Everything!
Nov. 4 – 11
Home in Uptown
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Dec. 9 – 16
Guest suite in Lake View
4.91 out of 5 average rating, 358 reviewsContemporary, private suite w fireplace
Apr. 16 – 23
Guesthouse in Chicago
4.99 out of 5 average rating, 783 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Oct. 25 – Nov. 1
Apartment in Chicago
4.78 out of 5 average rating, 269 reviewsCozy Garden-Subterranean Apartment
Sep. 26 – Oct. 3
Apartment in Andersonville
4.98 out of 5 average rating, 249 reviewsAndersonville Cozy 1 bedroom basement suite
Oct. 23 – 30
Quick stats about vacation rentals in Chicago
Total rentals
10K properties
Rentals with dedicated workspaces
6.6K properties have a dedicated workspace
Rentals with a pool
1.1K properties have a pool
Pet-friendly rentals
3.3K properties allow pets
Family-friendly rentals
4.8K properties are a good fit for families
Total number of reviews
466K reviews
Destinations to explore
- Downtown Chicago Vacation rentals
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- Rentals with an EV charger Chicago
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