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
Get the amount of space that is right for you
Popular amenities for Chicago holiday rentals
Other great holiday rentals in Chicago
Guest favourite
Flat in Chicago
4.96 out of 5 average rating, 267 reviewsCozy loft in Chicago's Uptown
20–27 Oct
₹9,436 per night
Guest favourite
Flat in Chicago
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
18–25 Dec
₹10,887 per night
Guest favourite
Flat in Roscoe Village
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
19–26 Nov
₹8,711 per night
Guest favourite
Guest house in Chicago
4.95 out of 5 average rating, 367 reviewsCozy Coach House
19–26 Aug
₹9,322 per night
Guest favourite
Guest suite in Logan Square
4.97 out of 5 average rating, 226 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
23–30 Sep
₹9,574 per night
Guest favourite
Flat in Logan Square
4.93 out of 5 average rating, 208 reviewsCozy Private Coach House
3–10 Jul
₹11,481 per night
Guest favourite
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
16–23 Jan
₹10,463 per night
Guest favourite
Guest house in Andersonville
4.91 out of 5 average rating, 342 reviewsPrivate, Charming, Coach House Loft in Andersonville
7–14 Dec
₹12,897 per night
Quick stats about holiday rentals in Chicago
Total rentals
10T properties
Rentals with dedicated workspaces
6.6T properties have a dedicated workspace
Rentals with a pool
1.1T properties have a pool
Pet-friendly rentals
3.3T properties allow pets
Family-friendly rentals
4.8T properties are a good fit for families
Total number of reviews
4.7L reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Family-friendly rentals Chicago
- Rentals with pools Chicago
- Waterfront rentals Chicago
- Family-friendly rentals Chicago
- Loft rentals Chicago
- Guest house rentals Chicago
- Private suite rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with lake access Chicago
- Rentals with a balcony Chicago
- Bed and breakfasts Chicago
- Cottage rentals Chicago
- Flat rentals Chicago
- Lakehouse rentals Chicago
- Hotel rentals Chicago
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- Rentals with a firepit Chicago
- Rentals with outdoor seating Chicago
- Rentals with an accessible-height bed Chicago
- Beachfront rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with a fireplace Chicago
- Apartment rentals Chicago
- Rentals with a sauna Chicago
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- Rentals with a cinema Chicago
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- Monthly Rentals Chicago
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- Rentals with a hot tub Chicago
- House rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Smoking-friendly rentals Chicago
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- Yurt Rentals United States
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