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
Guest suite in Logan Square
4.97 out of 5 average rating, 226 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
Sep. 10 – 17
Apartment in Chicago
4.96 out of 5 average rating, 263 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Jan. 3 – 10
Home in Berwyn
4.91 out of 5 average rating, 242 reviewsPrivate apartment with retro vibe
Sep. 8 – 15
Home in Chicago
4.89 out of 5 average rating, 333 reviewsPrivate 3rd Floor Apartment
Feb. 11 – 18
Apartment in Lincoln Park
4.83 out of 5 average rating, 211 reviewsCozy Lincoln Park Studio - Steps to Zoo!
Jan. 30 – Feb. 6
Apartment in Chicago
4.92 out of 5 average rating, 492 reviews2BR Bursting w/ Character in Hip Logan Square!
Mar. 27 – Apr. 3
Guest suite in Chicago
4.96 out of 5 average rating, 322 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
Apr. 13 – 20
Guesthouse in Little Italy
4.99 out of 5 average rating, 786 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Nov. 16 – 23
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
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