Hotel vacation rentals in Chicago
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Top-rated hotels in Chicago
Guests agree: these hotels 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 hotels
Family-friendly hotels
Boutique hotel in Chicago
4.78 out of 5 average rating, 91 reviewsLuxury 2BR Suite next to Loyola University
Apr. 1 – 8
Shared hotel room in Chicago
4.58 out of 5 average rating, 81 reviewsHotel Perks - Private Bedroom | Private Bathroom
Jan. 20 – 27
Boutique hotel in Chicago
4.67 out of 5 average rating, 6 reviews1BD Suite @ The Guesthouse Hotel(2)
Jul. 24 – 31
Boutique hotel in Chicago
4.97 out of 5 average rating, 38 reviews1BD Suite @ The Guesthouse Hotel
Jun. 20 – 27
Hotel room in Uptown
4.98 out of 5 average rating, 44 reviews1 BD Luxury Boutique Apartment
Jun. 18 – 25
Aparthotel in Chicago
4.85 out of 5 average rating, 20 reviews2BD Suite @The Guesthouse Hotel (2)
Oct. 1 – 8
Hotel room in Chicago
4.91 out of 5 average rating, 34 reviews2BD/2BA Luxury Apartment - Roof Deck Access
Jun. 24 – Jul. 1
Hotel room in Chicago
4.47 out of 5 average rating, 15 reviewsHotel Perks - Private Bedroom | Private Bathroom
Mar. 19 – 26
Hotels with a pool
Hotel in Westmont
4.53 out of 5 average rating, 43 reviewsKing Bed with a private tub (breakfast included)
Sep. 26 – Oct. 3
Hotel in Chicago
4.63 out of 5 average rating, 35 reviewsJust a short walk from Magnificent Mile! Pool!
Nov. 29 – Dec. 6
Hotel in Near North Side
5.0 out of 5 average rating, 6 reviewsHaven of Serenity! Pets Allowed, Onsite Pool
Mar. 20 – 27
Hotel in Chicago
5.0 out of 5 average rating, 7 reviewsLight-flooded rooms and city views
Jul. 10 – 17
Hotel in Chicago
5.0 out of 5 average rating, 4 reviewsComfort and Relaxation! Parking, Near Navy Pier
Jan. 23 – 30
Hotel in Schaumburg
3.67 out of 5 average rating, 3 reviews"Radisson Hotel Schaumburg"
Mar. 5 – 12
Hotel in Chicago
120-yr-old landmark with floor-to-ceiling views
Jul. 15 – 22
Hotel in Chicago
5.0 out of 5 average rating, 3 reviewsCozy Stay in River North! with Indoor Pool
Mar. 19 – 26
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
$96 CAD before taxes and fees
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