Find Hotels with an Outdoor Pool in Downtown Chicago, IL

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Top Downtown Chicago Hotels with an Outdoor Pool

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2181)
"Nice Hotel"
United States
Alan
$89 nightly
The price is $105
Dec 16 - Dec 17
Total with taxes and fees
DoubleTree by Hilton Chicago - Magnificent Mile

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (1005)
"Amazing staff clean and secure hotel "
United States
Aniyah
$111 nightly
The price is $131
Dec 25 - Dec 26
Total with taxes and fees
Holiday Inn & Suites Chicago - Downtown by IHG

Radisson Blu Aqua Hotel Chicago

4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1785)
"Friendly staff and good location to all of the city"
United States
Mark
$162 nightly
The price is $190
Dec 21 - Dec 22
Total with taxes and fees
Radisson Blu Aqua Hotel Chicago

Viceroy Chicago

4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1145)
" Great trip, hotel and location was very nice. Lots of stores and restaurants near by, walkable. "
United States
Julyana
$240 nightly
The price is $282
Jan 4 - Jan 5, 2026
Total with taxes and fees
Viceroy Chicago

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (324)
"Great accommodation, staff really nice, room was spacious and very clean. Perfect location to walk just about anywhere, "
United States
Lizbeth
$150 nightly
The price is $176
Dec 16 - Dec 17
Total with taxes and fees
Hilton Grand Vacations Club Chicago Magnificent Mile

The Hoxton Chicago

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1000)
"Love the Hoxton, it’s a beautiful hotel and the staff is amazing. "
United States
Sam
$174 nightly
The price is $204
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Hoxton Chicago

Level Chicago - River North

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (787)
"Great place amazing views very safe staff was very nice "
United States
Kenneth
$202 nightly
The price is $237
Dec 14 - Dec 15
Total with taxes and fees
Level Chicago - River North

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (394)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
$223 nightly
The price is $262
Jan 4 - Jan 5, 2026
Total with taxes and fees
Level Chicago – Old Town

Level Chicago Fulton Market

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (357)
"Great hotel!"
United States
Giselle
$212 nightly
The price is $249
Dec 14 - Dec 15
Total with taxes and fees
Level Chicago Fulton Market

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (181)
"Awesome stay "
United States
Sally
$347 nightly
The price is $407
Dec 9 - Dec 10
Total with taxes and fees
Kasa River North Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Price trends for hotels in Downtown Chicago

Less expensive
More expensive
This month
Next month
January
October
$110
$109
Month
Price
January
$109
February
$121
March
$157
April
$202
May
$298
June
$325
July
$294
August
$267
September
$329
October
$365
November
$293
December
$110
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Downtown Chicago. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Downtown Chicago

Discover top Downtown Chicago attractions

Downtown Chicago offers a blend of relaxation and adventure for travelers looking for a rejuvenating getaway. Start your day at Millennium Park, where you can unwind by the iconic Cloud Gate sculpture, known affectionately as "The Bean," and enjoy the serene gardens surrounding it. Just a short stroll away is the Art Institute of Chicago, a paradise of Impressionist masterpieces, providing a peaceful cultural experience that invites contemplation. For a leisurely afternoon, head to the Chicago Riverwalk, where you can sit by the water, savoring a coffee or a light meal from one of the riverside cafes, all while watching the city’s boats drift by. If you’re in the mood to explore, a visit to the historic Chicago Architecture River Cruise is a must, offering captivating views of the skyline from a unique perspective while providing a relaxing ambiance. Finally, don’t miss out on a pampering session at one of the local spas, where you can indulge in a massage or facial treatment. After a day of exploration, retreat to one of the downtown hotels that boast stunning rooftop pools, allowing you to soak in the skyline while lounging in style. Many of these hotels offer family-friendly amenities and personalized service, ensuring a comfortable stay where you can truly unwind after a busy day of discovery.

Find the best hotels with an outdoor pool in Downtown Chicago

For travelers looking to enjoy a refreshing dip during their stay in Downtown Chicago, these hotels feature inviting outdoor pools that enhance the experience of exploring the city.

Loews Chicago Hotel

  • Why it's great for poolside lounging: The Loews Chicago Hotel stands out for its accessible outdoor pool and a vibrant poolside bar, earning an impressive review rating of 9.4 from guests. This hotel provides an inviting atmosphere for travelers to unwind while enjoying a refreshing drink by the pool.
  • Other amenities: Guests can indulge in other excellent amenities including a rooftop terrace, 24-hour fitness facilities, and spacious rooms with stunning river views. The hotel also features a concierge service, an indoor pool, and comfortable accommodations with designer toiletries. With nearby beach access and shopping options, it effortlessly combines relaxation and convenience for a delightful stay.
  • Neighborhood: Downtown Chicago
  • Nearby attractions: Michigan Avenue - 0.52 miles, Chicago Riverwalk - 0.61 miles, Millennium Park - 0.55 miles

InterContinental Chicago Magnificent Mile by IHG

  • Why it's great for poolside lounging: For an upscale experience, the InterContinental Chicago Magnificent Mile impresses with its resort-style outdoor pool, rated 9.0 by guests. This luxurious hotel ensures travelers can relax in style, with the pool included in the resort fee, signifying an all-inclusive experience.
  • Other amenities: Beyond the outdoor swimming area, the hotel offers a lavish spa, fitness facilities, and fine dining options. Guests can delight in premium bedding, historic ambiance, and exceptional service with valet parking and early check-in. Additional features include electric car charging stations, shopping accessibility, and a range of treatments at the on-site spa, making it ideal for travelers seeking both relaxation and indulgence.
  • Neighborhood: Downtown Chicago
  • Nearby attractions: Michigan Avenue - 0.0 miles

Top Downtown Chicago Hotel Reviews

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