Holiday houses 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
Apartment in Cicero
4.98 out of 5 average rating, 201 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
21–28 Mar
$241 NZD 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
$184 NZD per night
Superhost
Loft in Wicker Park
4.78 out of 5 average rating, 482 reviewsWicker Park Loft - Walk To Everything!
4–11 Nov
$238 NZD per night
Guest favourite
Home in Uptown
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
9–16 Dec
$273 NZD 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
$172 NZD per night
Guest favourite
Guesthouse in Chicago
4.99 out of 5 average rating, 784 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
25 Oct – 1 Nov
$321 NZD per night
Guest favourite
Apartment in Chicago
4.78 out of 5 average rating, 269 reviewsCozy Garden-Subterranean Apartment
26 Sep – 3 Oct
$219 NZD per night
Guest favourite
Apartment in Andersonville
4.98 out of 5 average rating, 249 reviewsAndersonville Cozy 1 bedroom basement suite
23–30 Oct
$274 NZD 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 a hot tub Chicago
- Pet-friendly rentals Chicago
- Rentals with pools Chicago
- Rentals with a fireplace Chicago
- Condo rentals Chicago
- Hotel rentals Chicago
- Rentals with a home theatre Chicago
- Beachfront rentals Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- Fitness-friendly rentals Chicago
- Kid-friendly rentals Chicago
- Loft rentals Chicago
- Rentals with an accessible height bed Chicago
- Rentals with a sauna Chicago
- Bed and breakfasts Chicago
- House rentals Chicago
- Monthly Rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with a washing machine and dryer Chicago
- Family-friendly rentals Chicago
- Rentals with a fire pit Chicago
- Rentals with outdoor seating Chicago
- Waterfront rentals Chicago
- Rentals with breakfast Chicago
- Mansion rentals Chicago
- Rentals with a patio Chicago
- Apartment rentals Chicago
- Lakehouse rentals Chicago
- Boutique hotel rentals Chicago
- Townhouse rentals Chicago
- Villa rentals Chicago
- Cottage rentals Chicago
- Rentals with beach access Chicago
- Rentals with lake access Chicago
- Smoking-friendly rentals Chicago
- Rentals with a balcony Chicago
- Yurt Rentals United States
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