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.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Chicago vacation rentals
Other great vacation rentals in Chicago
Guest favourite
Apartment in Roscoe Village
4.95 out of 5 average rating, 240 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Guest favourite
Guesthouse in Edgewater
4.95 out of 5 average rating, 368 reviewsCozy Coach House
Guest favourite
Apartment in Chicago
4.99 out of 5 average rating, 231 reviewsA Whimsical Fairy-tale Loft in Ravenswood Chicago
Guest favourite
Home in West Loop
4.97 out of 5 average rating, 318 reviewsCozy garden apartment historic Jackson Bvld.
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 263 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Guest favourite
Apartment in Chicago
4.93 out of 5 average rating, 191 reviewsQuirky Designer Apartment - Steps from Wrigley!
Guest favourite
Guesthouse in Andersonville
4.91 out of 5 average rating, 342 reviewsPrivate, Charming, Coach House Loft in Andersonville
Guest favourite
Home in Chicago
4.89 out of 5 average rating, 333 reviewsPrivate 3rd Floor Apartment
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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- Fitness-friendly rentals Chicago
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