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 Lincoln Square
4.94 out of 5 average rating, 193 reviewsSpacious, light-drenched studio-private entrance!
Guest favourite
Apartment in West Town
4.96 out of 5 average rating, 265 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Guest favourite
Guest suite in Logan Square
4.97 out of 5 average rating, 227 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
Guest favourite
Guesthouse in Lincoln Square
4.88 out of 5 average rating, 229 reviewsPrivate Coach house near Lincoln Square!
Guest favourite
Guesthouse in Andersonville
4.91 out of 5 average rating, 343 reviewsPrivate, Charming, Coach House Loft in Andersonville
Guest favourite
Apartment in Lincoln Park
4.98 out of 5 average rating, 300 reviewsRedesigned Lower Level Studio in Historic Building
Guest favourite
Apartment in Logan Square
4.93 out of 5 average rating, 209 reviewsCozy Private Coach House
Guest favourite
Guest suite in Chicago
4.98 out of 5 average rating, 113 reviewsGorgeous Studio 15 Minutes From Ohare!
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
- Loft rentals Chicago
- Smoking-friendly rentals Chicago
- Family-friendly rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Lakehouse rentals Chicago
- Rentals with a home theatre Chicago
- Rentals with outdoor seating Chicago
- Fitness-friendly rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Kid-friendly rentals Chicago
- Bed and breakfasts Chicago
- Rentals with an accessible height bed Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- Rentals with pools Chicago
- Rentals with lake access Chicago
- Monthly Rentals Chicago
- Rentals with a sauna Chicago
- Rentals with a fireplace Chicago
- Waterfront rentals Chicago
- Rentals with beach access Chicago
- House rentals Chicago
- Mansion rentals Chicago
- Rentals with a balcony Chicago
- Apartment rentals Chicago
- Beachfront rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Boutique hotel rentals Chicago
- Townhouse rentals Chicago
- Rentals with a patio Chicago
- Rentals with an EV charger Chicago
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