Find Hotels with an Outdoor Pool in Wicker Park, IL

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Top Wicker Park Hotels with an Outdoor Pool

The Robey, Chicago, a Member of Design Hotels

3.5 star property
West Town
  • Pool loungers
9.2 out of 10, Wonderful, (1006)
Seasonal swimming meets city sophistication at this art deco hotel. Dive into the outdoor pool (open May to September), relax on sun loungers, and enjoy cocktails at the poolside bar, all complemented by an on-site cafe serving delicious American cuisine.
$157 nightly
The price is $184
Dec 7 - Dec 8
Total with taxes and fees
The Robey, Chicago, a Member of Design Hotels

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
Nov 25 - Nov 26
Total with taxes and fees
DoubleTree by Hilton 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, (1767)
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

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 star property
Downtown Chicago
  • Pool loungers
  • Near the beach
9.2 out of 10, Wonderful, (318)
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.
$120 nightly
The price is $141
Dec 15 - Dec 16
Total with taxes and fees
Hilton Grand Vacations Club Chicago Magnificent Mile

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, (1003)
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.
$110 nightly
The price is $129
Dec 12 - Dec 13
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, (1004)
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.
$168 nightly
The price is $197
Dec 14 - Dec 15
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, (1135)
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.
$240 nightly
The price is $282
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.
$229 nightly
The price is $269
Nov 24 - Nov 25
Total with taxes and fees
Kasa River North Chicago

Level Chicago – Old Town

4.0 star property
Downtown Chicago
  • Pool loungers
  • Near the beach
9.0 out of 10, Wonderful, (383)
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.
$312 nightly
The price is $366
Dec 14 - Dec 15
Total with taxes and fees
Level Chicago – Old Town

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, (767)
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.
$194 nightly
The price is $227
Dec 12 - Dec 13
Total with taxes and fees
Level Chicago - River North
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 Wicker Park

Discover top Wicker Park attractions

Wicker Park offers a vibrant blend of relaxation and adventure, making it a perfect spot for travelers seeking a serene getaway. Start your day with a leisurely stroll through the picturesque Wicker Park itself, where you can enjoy lush greenery, scenic walking paths, and perhaps even catch a local performance at the park's amphitheater. Just a short walk away, The 606 is an elevated trail that provides a unique biking or walking experience, surrounded by art installations and stunning city views. For a taste of local culture, visit the renowned Flat Iron Arts Building, home to numerous galleries and studios where you can engage with artists and discover unique pieces. After exploring, unwind at one of the cozy cafes like Intelligentsia Coffee, famous for its artisanal brews and inviting atmosphere. Finally, for family-friendly fun, head over to the nearby Lincoln Park Zoo, where kids can enjoy close encounters with animals in a welcoming, relaxed environment. When it comes to accommodations, Wicker Park boasts several hotels featuring inviting pools, allowing you to relax and rejuvenate after a day of exploring. Expect attentive service and modern amenities designed to make your stay comfortable, with some hotels even offering rooftop pools for a refreshing dip accompanied by stunning views of the Chicago skyline. Your experience in Wicker Park will be both memorable and pampering, ensuring that your family feels at home while enjoying the neighborhood’s unique charm.

Top Wicker Park Hotel Reviews

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