Find Hotels with an Outdoor Pool in Old Town Chicago, IL

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Top Old Town Chicago Hotels with an Outdoor Pool

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Downtown Chicago
  • Outdoor pool
  • Pool loungers
  • Near the beach
8.8 out of 10, Excellent, (2145)
Poolside bliss awaits with shaded cabanas, comfortable loungers, and refreshing cocktails from the bar. After swimming, guests can explore Michigan Avenue's attractions, dine at HotHouse restaurant, or energize in the fitness center.
$98 nightly
The price is $115
Dec 7 - Dec 8
Total with taxes and fees
DoubleTree by Hilton Chicago - Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 star property
Downtown Chicago
  • Pool loungers
  • Near the beach
9.2 out of 10, Wonderful, (320)
Poolside loungers beckon at the seasonal rooftop retreat, complete with refreshing cocktail service and city views. After swimming, guests explore nearby Millennium Park or unwind in spacious rooms featuring premium bedding and pillowtop mattresses.
$87 nightly
The price is $102
Nov 26 - Nov 27
Total with taxes and fees
Hilton Grand Vacations Club Chicago Magnificent Mile

Radisson Blu Aqua Hotel Chicago

4.5 star property
Downtown Chicago
  • Pool loungers
  • Near the beach
8.6 out of 10, Excellent, (1777)
Splash into aquatic bliss at both indoor and seasonal outdoor pools complete with complimentary cabanas and sun loungers. This luxury hotel offers basketball courts, FireLake restaurant, and sits within walking distance of Chicago Riverwalk and Millennium Park.
$162 nightly
The price is $190
Dec 14 - Dec 15
Total with taxes and fees
Radisson Blu Aqua Hotel Chicago

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
Downtown Chicago
  • Pool loungers
  • Near the beach
8.4 out of 10, Very Good, (1005)
Poolside loungers invite sun-soaked relaxation at this downtown Chicago retreat near Willis Tower. The seasonal outdoor pool complements the 24-hour health club, while premium bedding and deep soaking tubs await after city adventures.
$105 nightly
The price is $124
Nov 26 - Nov 27
Total with taxes and fees
Holiday Inn & Suites Chicago - Downtown by IHG

The Hoxton Chicago

4.0 star property
Downtown Chicago
  • Poolside bar
9.0 out of 10, Wonderful, (1006)
Mediterranean flavors await poolside at this eco-certified Chicago hotel where the seasonal rooftop pool becomes a social hub by day and a sophisticated bar venue by night, complemented by free bicycle rentals for urban exploration.
$166 nightly
The price is $194
Dec 21 - Dec 22
Total with taxes and fees
The Hoxton Chicago

Viceroy Chicago

4.5 star property
Downtown Chicago
  • Pool loungers
  • Near the beach
9.4 out of 10, Exceptional, (1134)
Seasonal rooftop swimming beckons with panoramic city vistas and premium loungers after exploring nearby Water Tower Place. Somerset restaurant serves exceptional breakfast while attentive staff ensures every comfort in elegant surroundings.
$197 nightly
The price is $231
Dec 7 - Dec 8
Total with taxes and fees
Viceroy Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
  • Pool loungers
9.4 out of 10, Exceptional, (179)
Seasonal rooftop pool creates an urban oasis amid Chicago's skyline from June through September. Sun loungers invite lazy afternoons after exploring nearby Michigan Avenue attractions or working out in the fitness center.
$347 nightly
The price is $407
Nov 25 - Nov 26
Total with taxes and fees
Kasa River North Chicago

Level Chicago Fulton Market

4.0 star property
Downtown Chicago
  • Pool
  • Pet friendly
  • Free WiFi
  • Air conditioning
  • Parking available
  • Business services
9.2 out of 10, Wonderful, (352)
Seasonal poolside relaxation awaits at this upscale Chicago retreat, where the outdoor swimming area complements stylish accommodations featuring rainfall showers and deep soaking tubs. Savor stunning city views from beautifully decorated rooms.
$207 nightly
The price is $243
Dec 7 - Dec 8
Total with taxes and fees
Level Chicago Fulton Market

Level Chicago - River North

4.0 star property
Downtown Chicago
  • Pool
  • Pet friendly
  • Free WiFi
  • Air conditioning
  • Gym
  • Parking available
9.0 out of 10, Wonderful, (772)
Poolside perfection awaits at this upscale Chicago retreat, where the seasonal swimming area complements fitness facilities and bike rentals. After splashing around, guests appreciate spacious rooms with full kitchens and premium bedding for total comfort.
$177 nightly
The price is $208
Dec 14 - Dec 15
Total with taxes and fees
Level Chicago - River North

Level Chicago – Old Town

4.0 star property
Downtown Chicago
  • Pool loungers
  • Near the beach
9.0 out of 10, Wonderful, (386)
Seasonal outdoor pool provides a refreshing escape from Chicago's bustling streets. After swimming, guests rejuvenate in the sauna and steam room or maintain fitness routines at the 24-hour health club with basketball courts.
$207 nightly
The price is $243
Nov 24 - Nov 25
Total with taxes and fees
Level Chicago – Old Town
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.

Find out more about Old Town Chicago

Discover top Old Town Chicago attractions

Old Town Chicago is a charming neighborhood that caters to travelers seeking relaxation and leisure. One of its highlights is the Lincoln Park Zoo, where families can explore lush gardens and see a diverse range of animals, making it a perfect spot for a leisurely day out with the kids. Just a short walk away, you can unwind at the picturesque Lincoln Park, featuring serene walking paths, beautiful picnic spots, and stunning views of Lake Michigan—ideal for a family afternoon or romantic stroll. For a unique cultural experience, visit the Old Town Art Fair, held annually, showcasing local artists and offering a vibrant atmosphere filled with live music and delicious food. Don't miss the historic Old Town Triangle District, where Victorian architecture and charming boutiques create a delightful backdrop for a leisurely shopping spree. As you explore, envision returning to one of the nearby hotels with pools, where you can relax in the water after a day of adventure. Many hotels here offer rooftop pools with stunning city views, providing the perfect place to soak up the sun while the kids splash around. With attentive service and family-friendly amenities, your stay in Old Town Chicago can be both refreshing and indulgent.

Find the best hotels with an outdoor pool in Old Town Chicago

For travelers seeking a refreshing escape in Old Town Chicago, these hotels feature stunning outdoor pools perfect for relaxation and enjoyment. Dive into comfort and luxury with these top recommendations.

Loews Chicago Hotel

  • Why it's great for poolside lounging: Loews Chicago Hotel is a luxurious retreat for guests who appreciate the finer things in life, including a stunning outdoor pool. With an impressive review rating of 9.2, this hotel features an accessible outdoor pool alongside a vibrant poolside bar, where guests can relax and rejuvenate under the sun.
  • Other amenities: This upscale hotel offers a 24-hour fitness center, valet parking, and beautifully designed rooms with river views. Guests can enjoy a terrace for breathtaking sights, and the hotel’s prime location allows easy access to downtown attractions. Additional features include an indoor pool for year-round enjoyment, designer toiletries, and a convenient onsite snack bar.
  • Neighborhood: Downtown Chicago
  • Nearby attractions: Michigan Avenue - 0.52 miles, Chicago Riverwalk - 0.61 miles, Millennium Park - 0.55 miles

Top Old Town Chicago Hotel Reviews

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