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
Flat in Roscoe Village
4.96 out of 5 average rating, 237 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
3–10 Nov
Loft in Forest Park
4.96 out of 5 average rating, 462 reviewsWalk to Oak Park from a Bright Madison Street Loft
9–16 Dec
Guest suite in Chicago
4.91 out of 5 average rating, 358 reviewsContemporary, private suite w fireplace
19–26 Apr
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
29 Nov – 6 Dec
Guest house in Little Italy
4.99 out of 5 average rating, 783 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
25 Oct – 1 Nov
Home in Berwyn
4.92 out of 5 average rating, 237 reviewsPrivate apartment with retro vibe
20–27 Sep
Flat in Chicago
4.98 out of 5 average rating, 248 reviewsAndersonville Cozy 1 bedroom basement suite
10–17 Sep
Flat in Chicago
4.96 out of 5 average rating, 321 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
28 Sep – 5 Oct
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 sauna Chicago
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- Rentals with a washing machine and dryer Chicago
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- Villa rentals Chicago
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- Wheelchair-accessible rentals Chicago
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- Rentals with a firepit Chicago
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- Cottage rentals Chicago
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- Lakehouse rentals Chicago
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- Flat rentals Chicago
- Monthly Rentals Chicago
- Rentals with an accessible-height bed Chicago
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- Boutique hotel rentals Chicago
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- Rentals with a cinema Chicago
- Hotel rentals Chicago
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- Mansion rentals Chicago
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- Bed and breakfasts Chicago
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