Hotel vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago hotel rentals
Family-friendly hotel rentals
Boutique hotel in Chicago
4.78 out of 5 average rating, 91 reviewsLuxury 2BR Suite next to Loyola University
Oct 14 – 21
Aparthotel in Chicago
4.85 out of 5 average rating, 20 reviews2BD Suite @The Guesthouse Hotel (2)
Jul 30 – Aug 6
Hotel room in Uptown
4.98 out of 5 average rating, 44 reviews1 BD Luxury Boutique Apartment
Sep 18 – 25
Boutique hotel in Chicago
4.97 out of 5 average rating, 38 reviews1BD Suite @ The Guesthouse Hotel
Aug 27 – Sep 3
Boutique hotel in Chicago
4.67 out of 5 average rating, 6 reviews1BD Suite @ The Guesthouse Hotel(2)
Jul 24 – 31
Hotel room in Chicago
4.91 out of 5 average rating, 34 reviews2BD/2BA Luxury Apartment - Roof Deck Access
Oct 3 – 10
Shared hotel room in Chicago
4.58 out of 5 average rating, 81 reviewsHotel Perks - Private Bedroom | Private Bathroom
Feb 7 – 14
Hotel room in Near North Side
4.4 out of 5 average rating, 30 reviewsHotel Perks - Private Bedroom | Private Bathroom
Nov 5 – 12
Hotel rentals with a pool
Hotel in Westmont
4.53 out of 5 average rating, 43 reviewsKing Bed with a private tub (breakfast included)
Dec 14 – 21
Hotel in Chicago
4.49 out of 5 average rating, 49 reviewsA quick drive to Navy Pier! Pool, Parking Onsite!
Aug 26 – Sep 2
Hotel in Chicago
5.0 out of 5 average rating, 3 reviewsComfort and Relaxation! Parking, Near Navy Pier
Jan 22 – 29
Hotel in Chicago
4.71 out of 5 average rating, 7 reviewsRelax and Unwind! Close to Water Tower Chicago!
Oct 22 – 29
Hotel in Chicago
5.0 out of 5 average rating, 6 reviewsLight-flooded rooms and city views
Jul 14 – 21
Hotel in Schaumburg
3.67 out of 5 average rating, 3 reviews"Radisson Hotel Schaumburg"
Nov 7 – 14
Hotel in Chicago
120-yr-old landmark with floor-to-ceiling views
Jun 15 – 22
Hotel in Chicago
4.5 out of 5 average rating, 4 reviewsA short drive to Willis Tower! 2 Comfortable Units
Nov 11 – 18
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
G$14,606 GYD before taxes and fees
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