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
Guest house in Lincoln Square
4.88 out of 5 average rating, 229 reviewsPrivate Coach house near Lincoln Square!
Guest favourite
Home in Chicago
4.9 out of 5 average rating, 335 reviewsPrivate 3rd Floor Apartment
Guest favourite
Guest suite in Chicago
4.98 out of 5 average rating, 113 reviewsGorgeous Studio 15 Minutes From Ohare!
Guest favourite
Flat in Cicero
4.98 out of 5 average rating, 204 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Guest favourite
Flat in Chicago
4.96 out of 5 average rating, 265 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Guest favourite
Home in Bridgeport
4.95 out of 5 average rating, 123 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
Guest favourite
Guest suite in Chicago
4.91 out of 5 average rating, 359 reviewsContemporary, private suite w fireplace
Guest favourite
Flat in Oak Park
4.85 out of 5 average rating, 533 reviewsLong stays welcome@warm&cute vintage 2BR
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
- Beachfront rentals Chicago
- Rentals with a fireplace Chicago
- Family-friendly rentals Chicago
- Rentals with lake access Chicago
- Rentals with a washing machine and dryer Chicago
- Hotel rentals Chicago
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- Mansion rentals Chicago
- Flat rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Family-friendly rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with pools Chicago
- Boutique hotel rentals Chicago
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- House rentals Chicago
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- Rentals with outdoor seating Chicago
- Guest house rentals Chicago
- Rentals with a sauna Chicago
- Lakehouse rentals Chicago
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- Rentals with a patio Chicago
- Rentals with an accessible-height bed Chicago
- Fitness-friendly rentals Chicago
- Rentals with beach access Chicago
- Bed and breakfasts Chicago
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- Monthly Rentals Chicago
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