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
Boutique hotel in Chicago
4.78 out of 5 average rating, 91 reviewsLuxury 2BR Suite next to Loyola University
22–29 Dec
Aparthotel in Chicago
4.85 out of 5 average rating, 20 reviews2BD Suite @The Guesthouse Hotel (2)
30 Jul – 6 Aug
Hotel room in Uptown
4.98 out of 5 average rating, 44 reviews1 BD Luxury Boutique Apartment
18–25 Sep
Boutique hotel in Chicago
4.97 out of 5 average rating, 38 reviews1BD Suite @ The Guesthouse Hotel
27 Aug – 3 Sep
Boutique hotel in Chicago
4.67 out of 5 average rating, 6 reviews1BD Suite @ The Guesthouse Hotel(2)
24–31 Jul
Hotel room in Chicago
4.91 out of 5 average rating, 34 reviews2BD/2BA Luxury Apartment - Roof Deck Access
3–10 Oct
Shared hotel room in Chicago
4.58 out of 5 average rating, 81 reviewsHotel Perks - Private Bedroom | Private Bathroom
18–25 Oct
Hotel room in Chicago
4.48 out of 5 average rating, 3623 reviewsHotel Perks - Private Bedroom | Private Bathroom
3–10 Jan
Hotels with a pool
Hotel in Chicago
4.61 out of 5 average rating, 33 reviewsJust a short walk from Magnificent Mile! Pool!
20–27 Nov
Hotel in Westmont
4.53 out of 5 average rating, 43 reviewsKing Bed with a private tub (breakfast included)
6–13 Dec
Hotel in Chicago
5.0 out of 5 average rating, 3 reviewsComfort and Relaxation! Parking, Near Navy Pier
20–27 Jan
Hotel in Chicago
5.0 out of 5 average rating, 6 reviewsLight-flooded rooms and city views
14–21 Jul
Hotel in Chicago
4.71 out of 5 average rating, 7 reviewsRelax and Unwind! Close to Water Tower Chicago!
23–30 Oct
Hotel in Schaumburg
3.67 out of 5 average rating, 3 reviews"Radisson Hotel Schaumburg"
2–9 Dec
Hotel in Gold Coast
120-yr-old landmark with floor-to-ceiling views
10–17 Jun
Hotel in Chicago
4.5 out of 5 average rating, 4 reviewsA short drive to Willis Tower! 2 Comfortable Units
8–15 Dec
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
$118 NZD before taxes and fees
Destinations to explore
- Downtown Chicago Holiday rentals
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