Holiday rentals in Chicago
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Top-rated holiday rentals in Chicago
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Chicago holiday rentals
Other great holiday rentals in Chicago
Superhost
Rental unit in Pilsen Historic District
4.84 out of 5 average rating, 273 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Guest favourite
Guest house in Andersonville
4.92 out of 5 average rating, 373 reviewsPrivate, Charming, Coach House Loft in Andersonville
Guest favourite
Rental unit in East Rogers Park
4.84 out of 5 average rating, 371 reviewsCozy Garden Unit In Edgewater
Guest favourite
Guest suite in Lincoln Square
4.91 out of 5 average rating, 447 reviewsCozy, Quiet, Garden Getaway!
Guest favourite
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 316 reviewsa SIMPLE place
Guest favourite
Rental unit in Forest Park
4.88 out of 5 average rating, 173 reviewsHome in Forest Park upstairs.
Superhost
Apartment in West Town
4.86 out of 5 average rating, 457 reviewsHumboldt Park Traveler's Lodge
Guest favourite
Rental unit in Lake View
4.97 out of 5 average rating, 274 reviewsThe Garden on Wayne
Quick stats about holiday rentals in Chicago
Total rentals
11K properties
Total number of reviews
514K reviews
Family-friendly rentals
5K properties are a good fit for families
Pet-friendly rentals
3.4K properties allow pets
Rentals with a pool
1.1K properties have a pool
Rentals with dedicated workspaces
6.9K properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Saugatuck Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- South Side Holiday rentals
- Schaumburg Holiday rentals
- Family-friendly rentals Chicago
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