Find Hotels with a Pool in Wicker Park, IL

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Check availability on Wicker Park Hotels with a Pool

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

The Robey, Chicago, a Member of Design Hotels

The Robey, Chicago, a Member of Design Hotels
3.5 star property
West Town
9.2 out of 10, Wonderful, (1001)
"Good location, great staff!"
United States
Veronica
The price is AED 468
AED 640 total
includes taxes & fees
4 Jan - 5 January 2026
The Robey, Chicago, a Member of Design Hotels
Indoor pool
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (2742)
"Clean room and friendly staff, overall good stay "
United States
eesaa saalik
The price is AED 282
AED 439 total
includes taxes & fees
11 Jan - 12 January 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Indoor pool
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1052)
"Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food."
United States
Hannah
The price is AED 360
AED 530 total
includes taxes & fees
2 Jan - 3 January 2026
Hyatt Centric Chicago Magnificent Mile
Indoor pool, open 5:00 AM to 11:00 PM, sun loungers
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3462)
"Amazing stay, beautiful view!"
United States
Joshua
The price is AED 422
AED 496 total
includes taxes & fees
29 Dec - 30 Dec
voco Chicago Downtown - Riverwalk by IHG
Indoor pool, open 7:00 AM to 10:00 PM, sun loungers
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2957)
"Great location, the staff was friendly and the room was very clean. "
United States
Breanna
The price is AED 290
AED 341 total
includes taxes & fees
14 Jan - 15 January 2026
Aloft Chicago Mag Mile
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1756)
"Clean and staff was courteous. "
United States
HANNAH
The price is AED 262
AED 307 total
includes taxes & fees
5 Jan - 6 January 2026
Hilton Garden Inn Chicago Downtown South Loop
Indoor pool
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2126)
"Loved and enjoyed our stay"
United States
Luis
The price is AED 407
AED 569 total
includes taxes & fees
21 Dec - 22 Dec
Palmer House a Hilton Hotel
Outdoor pool, cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2189)
"Yes, very clean room and great hospitality "
United States
leticia i Vasquez
The price is AED 328
AED 385 total
includes taxes & fees
21 Dec - 22 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (4238)
"Clean room, very friendly staff and great location "
United States
Marcia
The price is AED 300
AED 352 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Indoor pool
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2314)
"Wonderful customer service, great location! "
United States
Michelle
The price is AED 408
AED 596 total
includes taxes & fees
4 Jan - 5 January 2026
The Royal Sonesta 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.
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Top Wicker Park Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Good"
Ana 3-night trip
Posted 10 hours ago
Hyatt Regency Chicago

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Frequently asked questions

What are some accommodations with pools in Wicker Park?
Palmer House a Hilton Hotel: Hotel steps from State Street. Features a full-service spa, an indoor pool, and a 24-hour fitness center. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool, and flat-screen televisions. Hilton Chicago/Magnificent Mile Suites: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel: Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool, and a health club.
What is there to see and do in Wicker Park?
Explore places like Michigan Avenue, Wrigley Field, 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.