The Best Hotels with a Pool in Wicker Park, IL from NT$7,281 in 2026

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

Congress Plaza Hotel : Hotel, 2-minute walk from Michigan Avenue. Provides flat-screen televisions and an indoor pool. Omni Chicago Hotel : Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna. Hilton Chicago/Magnificent Mile Suites : Hotel, 3-minute walk from Millennium Park. Provides a full-service spa, an indoor pool, and a 24-hour fitness center. Hyatt Regency O'Hare Chicago : Hotel, 3-minute walk from Merchandise Mart. Provides 2 restaurants, an indoor pool, and a sauna.

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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.

NT$9,713 total

includes taxes & fees

Jul 27 - Jul 28

JW Marriott Chicago

Downtown Chicago

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

NT$13,255 total

includes taxes & fees

Aug 6 - Aug 7

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Chicago hotel offers refreshing stays with indoor pool, fitness center, and walkable Michigan Avenue access.

NT$9,315 total

includes taxes & fees

Jul 12 - Jul 13

Indoor pool, seasonal outdoor pool, free cabanas, sun loungers

Radisson Blu Aqua Hotel Chicago

Downtown Chicago

Luxurious indoor and seasonal outdoor pools form a relaxing oasis near Millennium Park and Michigan Avenue.

NT$9,685 total

includes taxes & fees

Jul 7 - Jul 8

Indoor pool, open 6:00 AM to 10:00 PM, sun loungers

Sheraton Grand Chicago Riverwalk

Downtown Chicago

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

NT$10,976 total

includes taxes & fees

Jul 7 - Jul 8

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.

NT$7,330 total

includes taxes & fees

Jul 9 - Jul 10

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

NT$7,938 total

includes taxes & fees

Jul 9 - Jul 10

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.

NT$7,559 total

includes taxes & fees

Jul 7 - Jul 8

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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

Hyatt Regency O'Hare Chicago

10/10 Excellent

"Very friendly and accommodating staff! Shuttle runs 24 hours. Highly recommend! Book your extended parking ahead of time."

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Stayed at the Magnificent Mile Suites for a couple get away. They offered valet parking for $82/night, $62/night self park. Used spothero to park a block and a half down for half the cost. BUT we did not have privileges to get the car whenever. Hotel does offer in/out privileges. We ubered and walked around the city. There are many forms of transportation to get around the city. Room was pretty clean, they offer a pool and fitness area. Overall good experience. Will stay again. "

Frequently asked questions

What are some accommodations with pools in Wicker Park?

Congress Plaza Hotel: Hotel, 2-minute walk from Michigan Avenue. Provides flat-screen televisions and an indoor pool. Omni Chicago Hotel: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna. Hilton Chicago/Magnificent Mile Suites: Hotel, 3-minute walk from Millennium Park. Provides a full-service spa, an indoor pool, and a 24-hour fitness center. Hyatt Regency O'Hare Chicago: Hotel, 3-minute walk from Merchandise Mart. Provides 2 restaurants, an indoor pool, and a sauna.

What is there to see and do in Wicker Park?

Explore places like United Center, Michigan Avenue, and Wrigley Field 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