
Hotel holiday rentals in Chicago
Find and book unique hotels on Airbnb
Top-rated hotels in Chicago
Guests agree: These hotels are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago hotels
Family-Friendly hotels

Hotel room in Near North Side
4.52 out of 5 average rating, 23 reviewsHotel Perks - Private Bedroom | Private Bathroom

Hotel room in Andersonville
4.67 out of 5 average rating, 6 reviews1BD/1BA steps away from local shops, entertainment

Hotel room in Uptown
4.91 out of 5 average rating, 35 reviewsSpacious 2BR near concert venues, Wrigley Field

Hotel room in Uptown
4.85 out of 5 average rating, 20 reviewsVibrant Andersonville 2BR w/ in-unit laundry

Hotel room in Uptown
4.98 out of 5 average rating, 44 reviewsBright 1BR w/ shared Roof Deck, close to beach
Hotels with a pool

Hotel room in Rosemont
4.75 out of 5 average rating, 12 reviewsClose To Chicago O'Hare Airport | Free Breakfast

Hotel room in Schaumburg
4 out of 5 average rating, 5 reviewsRadisson Hotel

Hotel room in Gold Coast
4.5 out of 5 average rating, 4 reviews120-yr-old landmark with floor-to-ceiling views

Hotel room in Streeterville
4.91 out of 5 average rating, 11 reviewsGuest 2 Queen Room at Aloft Chicago Mag Mile

Hotel room in Near North Side
4.71 out of 5 average rating, 7 reviewsRelax and Unwind! Close to Water Tower Chicago!

Hotel room in Near South Side
4.71 out of 5 average rating, 14 reviewsmodern design with VU Skyward rooftop bar

Hotel room in Schaumburg
4.23 out of 5 average rating, 13 reviewsQuiet, clean, comfortable hotel

Hotel room in Schaumburg
4.64 out of 5 average rating, 11 reviewsSparkling clean and quiet hotel!
Quick stats about hotel rentals in Chicago
Total rentals
380 properties
Nightly prices starting at
$18 NZD before taxes and fees
Total number of reviews
6.3K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
160 properties allow pets
Rentals with a pool
30 properties have a pool
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- Lake Michigan Beach Holiday rentals
- South Side Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
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