Book the Best Hotels with POOL in Wicker Park in 2026

Q: What are some accommodations with pools in Wicker Park?

Congress Plaza Hotel : Hotel, 3-minute walk from Merchandise Mart. Features 2 restaurants, an indoor pool, and a sauna. River Hotel : Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool, and a health club. Hotel Riu Plaza Chicago : Hotel, 2-minute walk from Michigan Avenue. Features flat-screen televisions and an indoor pool. Club Quarters Hotel, Central Loop, Chicago : Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool, and complimentary wireless internet access. Hotel Felix River North/Magnificent Mile : Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool, and flat-screen televisions.

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Our top choices for Wicker Park hotels with a pool

Seasonal outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas

The Robey, Chicago, a Member of Design Hotels

West Town

Seasonal outdoor pool paradise at the Art Deco Robey Hotel with poolside bar and views of Chicago's art scene.

CA $325 total

includes taxes & fees

May 25 - May 26

Palmer House a Hilton Hotel

Downtown Chicago

Dive into urban tranquility at the Palmer House pool, where historic charm meets modern luxury.

CA $342 total

includes taxes & fees

May 25 - May 26

Indoor pool, open 7:00 AM to 10:00 PM, sun loungers

Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Splash into the city at this downtown hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.

CA $224 total

includes taxes & fees

May 26 - May 27

The Wade

Downtown Chicago

Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.

CA $249 total

includes taxes & fees

May 26 - May 27

Sheraton Grand Chicago Riverwalk

Downtown Chicago

Riverside hotel offers waterfront relaxation with indoor pool near Michigan Avenue.

CA $441 total

includes taxes & fees

May 25 - May 26

Outdoor pool, cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.

CA $262 total

includes taxes & fees

May 26 - May 27

JW Marriott Chicago

Downtown Chicago

Sleek indoor pool sanctuary opens onto Chicago adventures in this luxury retreat.

CA $457 total

includes taxes & fees

May 25 - May 26

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Dive into downtown luxury with a rejuvenating pool experience close to Chicago landmarks.

CA $252 total

includes taxes & fees

May 27 - May 28

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Choose what matters most at hotels with a pool in Wicker Park

Breakfast included

4 stars

Top Wicker Park Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Great hotel! Only problem was it’s on a noisy street. Even on the 11th floor we were awakened by street noise."

Hilton Chicago

6/10 Okay

"We stayed 5 nights. Our looked out on beautiful Lake Michigan. We had an adjoining rooms which we could hear everything in the next room. The reason for a 3 star rating is we were there 5 nights. Our room was only cleaned 2 times. So on the days there was no room cleaning, when we got back at night we would have to get clean towels to shower. This hotel is very expensive and this unacceptable. Don't think we'd stay here again even though the location is good."

Frequently asked questions

What are some accommodations with pools in Wicker Park?

Congress Plaza Hotel: Hotel, 3-minute walk from Merchandise Mart. Features 2 restaurants, an indoor pool, and a sauna. River Hotel: Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool, and a health club. Hotel Riu Plaza Chicago: Hotel, 2-minute walk from Michigan Avenue. Features flat-screen televisions and an indoor pool. Club Quarters Hotel, Central Loop, Chicago: Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool, and complimentary wireless internet access. Hotel Felix River North/Magnificent Mile: Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool, and flat-screen televisions.

What is there to see and do in Wicker Park?

Explore places like Wrigley Field, Navy Pier, and United Center while you're in the area. Spend some time experiencing the great outdoors at Wood Street Gallery. Travelers love Wicker Park for its array of dining options.

When is the best time to book a hotel with a pool in Wicker Park?

You may want to think about an accommodation that offers an outdoor if you'll be visiting in the warmest months of July, August, or June when the average temp is 70°F. Lodging offering an indoor pool may be what you want if you visit during the coldest months of January, February, or December when the average temperature is 31°F.

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Our top choices for Wicker Park hotels with a pool