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.
Holiday rentals for every style
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Popular amenities for Chicago holiday rentals
Other great holiday rentals in Chicago
Guest house in Chicago
4.91 out of 5 average rating, 342 reviewsPrivate, Charming, Coach House Loft in Andersonville
15–22 Oct
Flat in Cicero
4.98 out of 5 average rating, 203 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
25 Apr – 2 May
Home in Chicago
4.89 out of 5 average rating, 333 reviewsPrivate 3rd Floor Apartment
19–26 Feb
Flat in Chicago
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
10–17 Dec
Flat in Chicago
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
31 Dec – 7 Jan
Guest house in Chicago
4.99 out of 5 average rating, 786 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
16–23 Nov
Home in Chicago
4.95 out of 5 average rating, 122 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
19–26 Dec
Home in Berwyn
4.91 out of 5 average rating, 242 reviewsPrivate apartment with retro vibe
20–27 Jul
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
- Hotel rentals Chicago
- Family-friendly rentals Chicago
- Loft rentals Chicago
- Boutique hotel rentals Chicago
- Family-friendly rentals Chicago
- Rentals with a cinema Chicago
- House rentals Chicago
- Cottage rentals Chicago
- Rentals with beach access Chicago
- Fitness-friendly rentals Chicago
- Rentals with a patio Chicago
- Rentals with a hot tub Chicago
- Rentals with a firepit Chicago
- Rentals with outdoor seating Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with an accessible-height bed Chicago
- Guest house rentals Chicago
- Private suite rentals Chicago
- Pet-friendly rentals Chicago
- Smoking-friendly rentals Chicago
- Bed and breakfasts Chicago
- Townhouse rentals Chicago
- Flat rentals Chicago
- Monthly Rentals Chicago
- Rentals with pools Chicago
- Rentals with an EV charger Chicago
- Rentals with lake access Chicago
- Rentals with a balcony Chicago
- Beachfront rentals Chicago
- Rentals with a sauna Chicago
- Waterfront rentals Chicago
- Lakehouse rentals Chicago
- Apartment rentals Chicago
- Rentals with a fireplace Chicago
- Mansion rentals Chicago
- Rentals with breakfast Chicago
- Yurt Rentals United States
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