Chicago

Chicago Hotels with Rooftop Pools

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We found 7 Chicago hotels with Rooftop Pools for you

Choose your travel dates to see the latest prices and deals.
Most Booked
Lowest price
Closest to downtown
Highest Rated
99+

Best Western River North Hotel

Hotel near River North,Chicago
Featured facilities: Swimming Pool, Bar, Fitness Room
Good
52 reviews
7.9/10
1 night
From AED 643
Check Availability
76

Hilton Grand Vacations Club Chicago Magnificent Mile

Hotel near Streeterville,Chicago
Featured facilities: Swimming Pool, Bar, Fitness Room
Great
101 reviews
9.1/10
1 night
From AED 808
Check Availability
99+

DoubleTree by Hilton Chicago Magnificent Mile

Hotel near Streeterville,Chicago
Featured facilities: Swimming Pool, Bar, Fitness Room
Very Good
282 reviews
8.8/10
1 night
From AED 960
Check Availability
99+

Viceroy Chicago

Hotel near River North,Chicago
Featured facilities: Swimming Pool, Sunbathing Area, Bar
Great
108 reviews
9.0/10
Check Availability
99+

Holiday Inn & Suites CHICAGO-DOWNTOWN by IHG

Hotels in Chicago
Featured facilities: Swimming Pool, Fitness Room, Laundry Service (On-Site)
Very Good
139 reviews
8.7/10
1 night
From AED 656
Check Availability
99+

Hyatt House Chicago West Loop

Hotel near West Loop,Chicago
Featured facilities: Swimming Pool, Bar, Fitness Room
Very Good
102 reviews
8.9/10
1 night
From AED 1,135
Check Availability
99+

The Robey, Chicago, a Member of Design Hotels

Hotel near Wicker Park,Chicago
Featured facilities: Swimming Pool, Bar, Massage Room
Great
101 reviews
9.1/10
1 night
From AED 895
Check Availability
See All Hotels with Rooftop Pools in Chicago

Frequently Asked Questions

What is the average price of a hotel in Chicago this weekend?

According to the latest 12-month data from Trip.com, the average price for a 3-star hotel in Chicago this weekend is AED 1,254 per night. For a 4-star hotel, the average cost is AED 1,612 per night. If you're looking for a luxury experience, 5-star hotels in Chicago this weekend typically cost AED 4,104 per night.

How much do hotels in Chicago cost per night on weekdays?

Based on the latest 12-month data from Trip.com, the average price for a 3-star hotel in Chicago during weekdays is AED 1,101 per night. For a 4-star hotel, you can expect to pay around AED 1,502 per night. If you're seeking a luxury stay, 5-star hotels in Chicago generally cost AED 3,755 per night on weekdays.

What are the best places to stay in Chicago?

Some of the best places to stay in Chicago are near popular attractions like Millennium Park, Willis Tower and Magnificent Mile, offering easy access to key sights and amenities.

What are the top hotels in Chicago near Millennium Park?

Some of the top hotels in Chicago near Millennium Park include The Palmer House Hilton (from AED 1,054), Swissotel Chicago (from AED 991) and L7 Chicago (from AED 1,104), all offering easy access to Millennium Park, making them ideal for visitors looking to explore the area.

Which hotels in Chicago are worth visiting for their spa experience?

Feel tired from travelling? Hilton Chicago O'Hare Airport (from AED 992), Hilton Garden Inn Chicago Downtown/Magnificent Mile (from AED 918) and Chicago Marriott Downtown Magnificent Mile (from AED 1,484) provide highly rated spa services.

Which hotels in Chicago have swimming pools?

Best Western River North Hotel (from AED 793), Hilton Garden Inn Chicago Downtown/Magnificent Mile (from AED 918) and Embassy Suites by Hilton Chicago Downtown River North (from AED 1,085) are hotels with swimming pools. Stay at any of these hotels to enjoy a swimming pool!

What hotels in Chicago offer an especially good breakfast ?

Swissotel Chicago (from AED 991),JW Marriott Chicago (from AED 1,869) and Trump International Hotel & Tower® Chicago (from AED 2,275) provide high-quality breakfast. Start your day with a delicious breakfast!

How to get good deals on hotels in Chicago?

To get the best hotel deals, try these Trip.com tips: 1. Log In Trip.com first and unlock member-only rates and Trip Coins (loyalty points). 2. Book Midweek: Sun–Thurs stays are much cheaper than weekends. 3. Set Price Alerts: Monitor price drops and rebook if needed. 4. Use “We Price Match” Policy: If you find a lower price elsewhere, Trip.com will refund the difference. 5. Avoid major holidays, conventions, and big events. 6. Check the Deals Page to see what promotions are available now on Trip.com.