Chicago

Chicago Hotels with Rooftop Pools

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We found 8 Chicago hotels with Rooftop Pools for you

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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
57 reviews
7.9/10
1 night
From €105
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
41 reviews
8.9/10
1 night
From €110
Check Availability
99+

DoubleTree by Hilton Chicago Magnificent Mile

Hotel near Streeterville,Chicago
Featured facilities: Swimming Pool, Bar, Fitness Room
Very Good
283 reviews
8.8/10
1 night
From €166
Check Availability
78

Hilton Grand Vacations Club Chicago Magnificent Mile

Hotel near Streeterville,Chicago
Featured facilities: Swimming Pool, Bar, Fitness Room
Great
101 reviews
9.0/10
1 night
From €248
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+

Hyatt House Chicago West Loop

Hotel near West Loop,Chicago
Featured facilities: Swimming Pool, Bar, Fitness Room
Very Good
104 reviews
8.9/10
1 night
From €262
Check Availability
96

The Hoxton, Chicago

Hotel near West Loop,Chicago
Featured facilities: Swimming Pool, Bar, Fitness Room
Great
101 reviews
9.0/10
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 €201
Check Availability
See All Hotels with Rooftop Pools in Chicago

What's new in Chicago

Updated on October 26, 2026

Navy Pier Winter Fireworks Show

The spectacular, free, and award-winning fireworks display at Navy Pier returns for winter 2026! Experience the magic of winter fireworks every Saturday night at 8 p.m.! Enjoy a comfortable evening on the pier, watching the dazzling fireworks and breathtaking city skyline views!

Navy Pier’s Winter WonderFest

Winter Wonder Festival at Navy Pier — Chicago Holiday Experience Winter Wonder Festival: Experience magical holiday fun at Chicago's Navy Pier with a stunning 42-foot Christmas tree, thrilling rides (Cliff Drift, Zero Gravity, bumper cars), ice skating, and seasonal attractions for all ages.

The Wintrust Magnificent Mile Lights Festival

Wintrust Grand Parade of Lights — 35th Annual Wintrust Grand Parade of Lights: America's largest nighttime parade on November 21st featuring Mickey and Minnie Mouse, Disney floats, marching bands, Santa, the Wintrust Fireworks Show, and millions of lights along North Michigan Avenue!

Frequently Asked Questions

What are popular hotels with high-quality breakfasts in Chicago?

Warwick Allerton Chicago (from €81),Hilton Chicago O'Hare Airport (from €172) and Swissotel Chicago (from €175) are popular hotels with high-quality breakfast. Start your wonderful journey with tasty breakfast!

What hotels in Chicago offer airport shuttle?

Are you worried about transportation in Chicago? Holiday Inn CHICAGO O'HARE AREA by IHG (from €109), Renaissance Chicago O'Hare Suites Hotel (from €128) and SpringHill Suites Chicago O'Hare (from €103) are popular hotels providing airport transfer services.

What are available deals for hotels in Chicago?

There are multiple promotions and discounts all year round for Trip.com users . Please check the promotions page to see what promotions are available now on Trip.com.

Which popular hotels in Chicago offer free Wi-Fi ?

Whether you're traveling on business or for vacation, internet connection is an essential facility. Warwick Allerton Chicago (from €81), HI Chicago Hostel (from €38) and Best Western Grant Park Hotel (from €116) are popular hotels with free Wi-Fi.

Which hotels in Chicago have swimming pools?

Best Western River North Hotel (from €105), Hilton Garden Inn Chicago Downtown/Magnificent Mile (from €118) and Embassy Suites by Hilton Chicago Downtown River North (from €147) provide awesome swimming pools. Book now and enjoy your swimming pool!

What are the best sap hotels in Chicago?

A spa treatment can be the perfect way to unwind after a long day of travel. Warwick Allerton Chicago (from €81), HI Chicago Hostel (from €38) and Best Western Grant Park Hotel (from €116) provide wonderful spa services.