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 Cicero
4.98 out of 5 average rating, 201 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
21–28 Mar
$168 SGD per night
Guest favourite
Guest suite in Chicago
4.96 out of 5 average rating, 319 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
13–20 Feb
$122 SGD per night
Superhost
Loft in Wicker Park
4.78 out of 5 average rating, 482 reviewsWicker Park Loft - Walk To Everything!
4–11 Nov
$140 SGD per night
Guest favourite
Home in Uptown
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
9–16 Dec
$171 SGD per night
Guest favourite
Guest suite in Lake View
4.91 out of 5 average rating, 358 reviewsContemporary, private suite w fireplace
16–23 Apr
$106 SGD per night
Guest favourite
Guest house in Chicago
4.99 out of 5 average rating, 783 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
25 Oct – 1 Nov
$196 SGD per night
Guest favourite
Flat in Chicago
4.78 out of 5 average rating, 269 reviewsCozy Garden-Subterranean Apartment
26 Sep – 3 Oct
$140 SGD per night
Guest favourite
Flat in Andersonville
4.98 out of 5 average rating, 249 reviewsAndersonville Cozy 1 bedroom basement suite
23–30 Oct
$171 SGD per night
Quick stats about holiday 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
- 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
- Rentals with an EV charger Chicago
- Rentals with breakfast Chicago
- Villa rentals Chicago
- Cottage rentals Chicago
- House rentals Chicago
- Rentals with pools Chicago
- Bed and breakfasts Chicago
- Smoking-friendly rentals Chicago
- Rentals with a patio Chicago
- Rentals with a balcony Chicago
- Boutique hotel rentals Chicago
- Rentals with lake access Chicago
- Rentals with a fireplace Chicago
- Wheelchair-accessible rentals Chicago
- Rentals with an accessible-height bed Chicago
- Apartment rentals Chicago
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- Rentals with a washing machine and dryer Chicago
- Family-friendly rentals Chicago
- Loft rentals Chicago
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- Guest house rentals Chicago
- Private suite rentals Chicago
- Rentals with a cinema Chicago
- Rentals with a hot tub Chicago
- Rentals with a sauna Chicago
- Lakehouse rentals Chicago
- Flat rentals Chicago
- Rentals with a firepit Chicago
- Rentals with outdoor seating Chicago
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- Townhouse rentals Chicago
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- Fitness-friendly rentals Chicago
- Yurt Rentals United States
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- Farm Houses United States
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- Holiday Chalets United Kingdom
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- Holiday Apartments Australia
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- Large Villas United Kingdom
- House Rentals with a Pool United States
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- Apartments with a Hot Tub United States
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