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Find Hotels with a Pool in Wicker Park, IL from CA $224

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Check availability on Wicker Park Hotels with a Pool

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for Wicker Park hotels with a pool

A rooftop pool area with lounge chairs and umbrellas, a city skyline view, and a no diving sign.

1. 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, (999 reviews)
  • cleanliness
    Seasonal outdoor pool paradise at the Art Deco Robey Hotel with poolside bar and views of Chicago's art scene.
The price is CA $303
CA $391 total
includes taxes & fees
Nov 1 - Nov 2
The Robey, Chicago, a Member of Design Hotels
A hotel with a swimming pool, outdoor seating, and a view of the city skyline.

2. The Hotel at Midtown

The Hotel at Midtown
4.0 star property
Bucktown
9.0 out of 10, Wonderful, (926 reviews)
  • cleanliness
    Dive into tennis and spa bliss at this wellness-focused hotel with two pools and luxurious amenities.
The price is CA $326
CA $458 total
includes taxes & fees
Nov 1 - Nov 2
The Hotel at Midtown
A modern indoor swimming pool with clear blue water, large windows offering city views, and a poolside area with chairs and a sun lounger.

3. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,305 reviews)
  • cleanliness
    Splashy indoor pool luxury awaits with designer touches in Chicago's West Loop scene.
The price is CA $275
CA $327 total
includes taxes & fees
Nov 1 - Nov 2
Hyatt House Chicago/West Loop-Fulton Market
A rooftop pool area with lounge chairs and a view of the city skyline.

4. The Hoxton, Chicago

The Hoxton, Chicago
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat.
The price is CA $355
CA $464 total
includes taxes & fees
Nov 1 - Nov 2
The Hoxton, Chicago
A hotel pool area with a clear view of the cityscape through large windows, a pool with a metal ladder, and several lounge chairs.

5. Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Splash into urban relaxation at this West Loop hotel's stylish indoor pool, where sun loungers invite post-sightseeing unwinding.
The price is CA $340
CA $404 total
includes taxes & fees
Oct 30 - Oct 31
Hampton Inn Chicago West Loop Fulton Market Area
A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.

6. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (3,353 reviews)
  • cleanliness
    World-class indoor pool in downtown offers lap swimming and family fun at this luxury hotel.
The price is CA $302
CA $409 total
includes taxes & fees
Oct 31 - Nov 1
InterContinental Chicago Magnificent Mile by IHG
An indoor swimming pool with a view of a brick building through large windows. There are seating areas with tables and chairs.

7. Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,353 reviews)
  • cleanliness
    Soak in relaxation at this historic Chicago hotel's indoor pool with spa amenities nearby.
The price is CA $236
CA $323 total
includes taxes & fees
Oct 30 - Oct 31
Hilton Chicago
A modern indoor pool area with lounge chairs, a wooden table, and large windows.

8. Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC
2.5 star property
Near West Side
9.6 out of 10, Exceptional, (782 reviews)
  • cleanliness
    Sleek indoor pool oasis at Chicago medical district hotel offers year-round swimming bliss.
The price is CA $288
CA $343 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Chicago Medical District UIC
An indoor swimming pool with a skylight, tiled floor, and poolside seating.

9. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
3.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,570 reviews)
  • cleanliness
    Splash into downtown luxury at this Hampton Inn with stylish indoor pool and river proximity.
The price is CA $197
CA $235 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Chicago Downtown
An indoor swimming pool with lounge chairs and a sofa, large windows with a view of the city, and a high ceiling with skylights.

10. The Wade

The Wade
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,121 reviews)
  • cleanliness
    Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.
The price is CA $202
CA $241 total
includes taxes & fees
Nov 1 - Nov 2
The Wade
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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Choose what matters most at hotels with a pool in Wicker Park

Breakfast included
4 stars

Top Wicker Park Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Friendly staff, great location"
Anna 1-night trip
Posted less than an hour ago
Hilton Chicago

Frequently asked questions

What are some accommodations with pools in Wicker Park?
River Hotel: Hotel, 2-minute walk from Grant Park. Features 2 restaurants, an indoor pool, and a health club. Congress Plaza Hotel: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna. The Chicago Hotel Collection Ambassador Gold Coast: Hotel, 8-minute walk from Lake Michigan. Offers complimentary wireless internet access, an indoor pool, and a 24-hour fitness center.
What is there to see and do in Wicker Park?
Explore places like Wrigley Field, Navy Pier, and Soldier 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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