Hotel holiday rentals in Chicago
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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
Aparthotel in Chicago
4.85 out of 5 average rating, 20 reviews2BD/2BA in Charming & Vibrant Andersonville
Hotel room in Uptown
4.98 out of 5 average rating, 44 reviews1BD/1BA Boutique Suite Near Wrigley, Uptown
Boutique hotel in Uptown
4.97 out of 5 average rating, 38 reviews1BD/1BA Suite with Full Kitchen, Balcony w/ Grill
Hotel room in Uptown
4.91 out of 5 average rating, 34 reviews2BD/2BA Near Concert Venues, Wrigley Field
Boutique hotel in Chicago
4.67 out of 5 average rating, 6 reviews1BD/1BA Steps Away from Local Shops, Entertainment
Shared hotel room in Chicago
4.58 out of 5 average rating, 81 reviewsHotel Perks - Private Bedroom | Private Bathroom
Hotel room in Chicago
4.47 out of 5 average rating, 3678 reviewsHotel Perks - Private Bedroom | Private Bathroom
Hotel room in Near North Side
4.47 out of 5 average rating, 15 reviewsHotel Perks - Private Bedroom | Private Bathroom
Hotels with a pool
Hotel in Westmont
4.5 out of 5 average rating, 46 reviewsKing Bed with a private tub (breakfast included)
Hotel in West Loop
5.0 out of 5 average rating, 8 reviewsLight-flooded rooms and city views
Hotel in Chicago
4.71 out of 5 average rating, 7 reviewsRelax and Unwind! Close to Water Tower Chicago!
Hotel in Chicago
5.0 out of 5 average rating, 5 reviewsComfort and Relaxation! Parking, Near Navy Pier
Hotel in Chicago
4.5 out of 5 average rating, 4 reviewsA short drive to Willis Tower! 2 Comfortable Units
Hotel in Chicago
120-yr-old landmark with floor-to-ceiling views
Hotel in Chicago
4.5 out of 5 average rating, 6 reviewsLarge Unit Close to the Millennium Park! Parking!
Hotel in Near North Side
4.83 out of 5 average rating, 12 reviewsHaven of Serenity! Pets Allowed, Onsite Pool
Quick stats about hotel rentals in Chicago
Total rentals
240 properties
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
3.5K reviews
Nightly prices starting at
$114 NZD before taxes and fees
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
- Aparthotel rentals United States
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