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
Guest suite in Lake View
4.91 out of 5 average rating, 361 reviewsContemporary, private suite w fireplace
Guest favourite
Apartment in Humboldt Park
4.98 out of 5 average rating, 110 reviewsHumboldt Park Loft
Guest favourite
Apartment in Near North Side
4.83 out of 5 average rating, 567 reviewsGreat Location! Gold Coast! 07
Guest favourite
Guesthouse in Chicago
4.99 out of 5 average rating, 792 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Guest favourite
Apartment in Gold Coast
4.89 out of 5 average rating, 141 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Guest favourite
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 297 reviewsa SIMPLE place
Guest favourite
Apartment in Lincoln Park
4.98 out of 5 average rating, 304 reviewsRedesigned Lower Level Studio in Historic Building
Guest favourite
Apartment in Lincoln Square
4.94 out of 5 average rating, 193 reviewsSpacious, light-drenched studio-private entrance!
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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- Rentals with lake access Chicago
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