Chicago

Hotels with Rooftop Pools in Chicago

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8 Chicago Hotels with Rooftop Pools Found 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: Pool, Bar, Gym
Good
57 reviews
7.9/10
1 night
From IDR 2,139,829
Check availability
99+

Holiday Inn & Suites CHICAGO-DOWNTOWN by IHG

Hotels in Chicago
Featured facilities: Pool, Gym, Laundry service (on-site)
Very Good
41 reviews
8.9/10
1 night
From IDR 2,229,670
Check availability
99+

DoubleTree by Hilton Chicago Magnificent Mile

Hotel near Streeterville,Chicago
Featured facilities: Pool, Bar, Gym
Very Good
283 reviews
8.8/10
1 night
From IDR 3,375,812
Check availability
78

Hilton Grand Vacations Club Chicago Magnificent Mile

Hotel near Streeterville,Chicago
Featured facilities: Pool, Bar, Gym
Great
101 reviews
9.0/10
1 night
From IDR 5,036,494
Check availability
99+

Viceroy Chicago

Hotel near River North,Chicago
Featured facilities: 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: Pool, Bar, Gym
Very Good
104 reviews
8.9/10
1 night
From IDR 5,319,627
Check availability
96

The Hoxton, Chicago

Hotel near West Loop,Chicago
Featured facilities: Pool, Bar, Gym
Great
101 reviews
9.0/10
Check availability
99+

The Robey, Chicago, a Member of Design Hotels

Hotel near Wicker Park,Chicago
Featured facilities: Pool, Bar, Massage room
Great
101 reviews
9.1/10
1 night
From IDR 4,072,754
Check availability
See All Hotels With Rooftop Pools in Chicago

What's new in Chicago

Updated on October 27, 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!

FAQs

What is the average price of a hotel in Chicago for 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 IDR 5,086,124 per night. For a 4-star hotel, the average cost is IDR 6,812,988 per night. If you're looking for a luxury experience, 5-star hotels in Chicago this weekend typically cost IDR 18,284,570 per night.

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

Based on the latest 12-month data from Trip.com, the average price for a 3-star hotel in Chicago during weekdays is IDR 4,490,130 per night. For a 4-star hotel, you can expect to pay around IDR 6,207,003 per night. If you're seeking a luxury stay, 5-star hotels in Chicago generally cost IDR 16,771,063 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 IDR 3,089,957), Swissotel Chicago (from IDR 3,558,215) and L7 Chicago (from IDR 2,670,703), all offering easy access to Millennium Park, making them ideal for visitors looking to explore the area.

What is the best spa hotel in Chicago?

Getting tired after a long walk? Warwick Allerton Chicago (from IDR 1,647,069), HI Chicago Hostel (from IDR 775,892) and Best Western Grant Park Hotel (from IDR 2,363,068) provide highly rated spa services.

Which hotels in Chicago provide airport transfers?

Worried about getting lost in Chicago? Holiday Inn CHICAGO O'HARE AREA by IHG (from IDR 2,229,669), Renaissance Chicago O'Hare Suites Hotel (from IDR 2,599,919) and SpringHill Suites Chicago O'Hare (from IDR 2,109,882) provide airport transfer services.

What are some hotels with pools in Chicago?

Best Western River North Hotel (from IDR 2,134,384), Hilton Garden Inn Chicago Downtown/Magnificent Mile (from IDR 2,406,627) and Embassy Suites by Hilton Chicago Downtown River North (from IDR 2,989,227) are hotels with swimming pools. Stay at any of these hotels to enjoy a swimming pool!

Where can you find hotels with excellent breakfast in Chicago?

Warwick Allerton Chicago (from IDR 1,647,069),Hilton Chicago O'Hare Airport (from IDR 3,503,766) and Swissotel Chicago (from IDR 3,558,215) provide high-quality breakfast. Start your day with fresh, delicious breakfast!

Where can I find the best hotel discounts in Chicago?

Trip.com provides various promotions and discounts for users all year round. You can check the promotions page to see what promotions are available on Trip.com.