Book the Best Hotels with POOL in Kenwood in 2026

Q: What are some accommodations with pools in Kenwood?

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.

A large classical building with a green dome and columns, surrounded by snow-covered ground and leafless trees.

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Our top choices for Kenwood hotels with a pool

An indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

1. Hilton Chicago

Downtown Chicago

Soak in relaxation at this historic Chicago hotel's indoor pool with spa amenities nearby.

CA $323 total

includes taxes & fees

Oct 30 - Oct 31

A modern indoor swimming pool with clear glass walls, a poolside seating area with chairs, and large windows offering views of the outside.

2. Hampton Inn Chicago McCormick Place

South Loop

Dive into a refreshing Chicago escape at this hotel with an indoor pool, steps from Wintrust Arena and McCormick Place.

CA $272 total

includes taxes & fees

Nov 1 - Nov 2

A modern indoor swimming pool with clear glass walls, a seating area with chairs and red vases, and large windows offering a view of the city.

3. Hilton Garden Inn Chicago McCormick Place

South Loop

CA $270 total

includes taxes & fees

Nov 1 - Nov 2

4. Home2 Suites by Hilton Chicago McCormick Place

South Loop

CA $259 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with lounge chairs and a sofa, large windows with a view of the city, and a high ceiling with skylights.

5. 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 $241 total

includes taxes & fees

Nov 1 - Nov 2

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

6. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

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

CA $235 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with lounge chairs and exercise equipment.

7. Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, hot tub haven, and 24-hour fitness centre.

CA $329 total

includes taxes & fees

Oct 31 - Nov 1

A modern hotel with a rooftop pool, surrounded by high-rise buildings and a clear view of the city skyline.

8. Radisson Blu Aqua Hotel Chicago

Downtown Chicago

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

CA $445 total

includes taxes & fees

Oct 31 - Nov 1

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Choose what matters most at hotels with a pool in Kenwood

Breakfast included

4 stars

Top Kenwood Hotel Reviews

Warwick Allerton - Chicago

10/10 Excellent

"We had plenty of space in our suite. Clean and quiet. Good location."

Sports Illustrated Resorts Chicago

10/10 Excellent

"Since Our flight kept being delayed; we arrived very early next day. We notified the front desk when this was happening. Upon our arrival, we were greeted with a friendly front desk person. Our room was ready. The room was spacious. It was beautiful. Staff in the front desk were very friendly and helpful."

Frequently asked questions

What are some accommodations with pools in Kenwood?

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 Kenwood?

Explore places like Lake Michigan while you're in Kenwood. Make a point to visit attractions like 49th Street Beach and Burnham Park. Kenwood appeals to visitors with its beautiful lakeside setting and array of dining options.

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

You may want to consider an accommodation with an outdoor swimming pool if you plan to visit in the warmest months of July, August, or June when the average temperature is 70°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temperature is 31°F.

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