Hotel holiday rentals in Chicago
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Top-rated hotel rentals in Chicago
Guests agree: these hotel rentals 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 hotel rentals in Chicago
Family-friendly hotel rentals
Hotel room in Andersonville
1BD Suite @ The Guesthouse Hotel(2)
Hotel room in Uptown
1 BD Luxury Boutique Apartment
Hotel room in Uptown
2BD Suite @The Guesthouse Hotel (2)
Hotel room in Uptown
1BD Suite @ The Guesthouse Hotel
Hotel room in Uptown
2BD/2BA Luxury Apartment - Roof Deck Access
Shared hotel room in Near North Side
Hotel Perks - Private Bedroom | Private Bathroom
Hotel room in Near North Side
Hotel Perks - Private Bedroom | Private Bathroom
Hotel room in Near North Side
Hotel Perks - Private Bedroom | Private Bathroom
Hotel rentals with a pool
Hotel room in Westmont
King Bed with a private tub (breakfast included)
Hotel room in Near North Side
Haven of Serenity! Pets Allowed, Onsite Pool
Hotel room in West Loop
Light-flooded rooms and city views
Hotel room in Streeterville
Comfort and Relaxation! Parking, Near Navy Pier
Hotel room in River North
A short drive to Willis Tower! 2 Comfortable Units
Hotel room in Gold Coast
120-yr-old landmark with floor-to-ceiling views
Hotel room in River North
Large Unit Close to the Millennium Park! Parking!
Hotel room in Near North Side
Relax and Unwind! Close to Water Tower Chicago!
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
€ 64 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
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