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
Hotel room in Uptown
4.98 out of 5 average rating, 44 reviews1 BD Luxury Boutique Apartment
18 – 25 June
Boutique hotel in Chicago
4.97 out of 5 average rating, 38 reviews1BD Suite @ The Guesthouse Hotel
20 – 27 June
Aparthotel in Chicago
4.85 out of 5 average rating, 20 reviews2BD Suite @The Guesthouse Hotel (2)
30 July – 6 Aug
Boutique hotel in Chicago
4.67 out of 5 average rating, 6 reviews1BD Suite @ The Guesthouse Hotel(2)
24 – 31 July
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
20 – 27 Jan
Hotel room in Chicago
4.48 out of 5 average rating, 3624 reviewsHotel Perks - Private Bedroom | Private Bathroom
13 – 20 Feb
Hotels with a pool
Hotel in Westmont
4.53 out of 5 average rating, 43 reviewsKing Bed with a private tub (breakfast included)
28 May – 4 June
Hotel in Near North Side
5.0 out of 5 average rating, 3 reviewsHaven of Serenity! Pets Allowed, Onsite Pool
25 Jan – 1 Feb
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 July
Hotel in Schaumburg
3.67 out of 5 average rating, 3 reviews"Radisson Hotel Schaumburg"
19 – 26 Mar
Hotel in Chicago
120-yr-old landmark with floor-to-ceiling views
10 – 17 June
Hotel in Chicago
5.0 out of 5 average rating, 3 reviewsCozy Stay in River North! with Indoor Pool
10 – 17 May
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
$107 AUD before taxes and fees
Destinations to explore
- Downtown Chicago Holiday rentals
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