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 suite in Chicago
4.98 out of 5 average rating, 111 reviewsGorgeous Studio 15 Minutes From Ohare!
10–17 Apr
Flat in Chicago
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
18–25 Nov
Flat in Chicago
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
14–21 Dec
Guest suite in Highland Park
4.96 out of 5 average rating, 111 reviewsCharming in-law suite w/ use of deck and yard
27 Jun – 4 Jul
Flat in Chicago
4.96 out of 5 average rating, 262 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
6–13 Nov
Guest suite in Chicago
4.97 out of 5 average rating, 226 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
29 Sep – 6 Oct
Flat in Chicago
4.81 out of 5 average rating, 124 reviewsTranquil & Airy 1BR Apt in Lincoln Square
7–14 May
Home in Chicago
4.94 out of 5 average rating, 210 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
23 Feb – 2 Mar
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 balcony Chicago
- Rentals with a washing machine and dryer Chicago
- Monthly Rentals Chicago
- Townhouse rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with a patio Chicago
- Rentals with an accessible-height bed Chicago
- Rentals with a sauna Chicago
- Rentals with a hot tub Chicago
- Rentals with breakfast Chicago
- Boutique hotel rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with a firepit Chicago
- Rentals with outdoor seating Chicago
- Beachfront rentals Chicago
- Cottage rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with beach access Chicago
- Fitness-friendly rentals Chicago
- Mansion rentals Chicago
- Guest house rentals Chicago
- Private suite rentals Chicago
- House rentals Chicago
- Rentals with pools Chicago
- Smoking-friendly rentals Chicago
- Family-friendly rentals Chicago
- Loft rentals Chicago
- Family-friendly rentals Chicago
- Flat rentals Chicago
- Lakehouse rentals Chicago
- Hotel rentals Chicago
- Rentals with lake access Chicago
- Waterfront rentals Chicago
- Bed and breakfasts Chicago
- Apartment rentals Chicago
- Rentals with a cinema Chicago
- Yurt Rentals United States
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