The Best Hotels with a Pool in Kenwood, IL from ￥33,366 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. The Chicago Hotel Collection Ambassador Gold Coast : Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel : 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.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Kenwood Hotels with a Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Kenwood hotels with a pool

A hotel pool area with a clear view of the cityscape through large windows, a pool with a metal ladder, and several lounge chairs.

1. Hampton Inn Chicago West Loop Fulton Market Area

Downtown Chicago

Splash into urban relaxation at this West Loop hotel's stylish indoor pool, where sun loungers invite post-sightseeing unwinding.

￥33,366 total

includes taxes & fees

Sep 27 - Sep 28

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

2. The Wade

Downtown Chicago

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

￥36,974 total

includes taxes & fees

Sep 20 - Sep 21

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

3. Hilton Chicago

Downtown Chicago

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

￥48,397 total

includes taxes & fees

Sep 27 - Sep 28

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

4. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

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

￥43,626 total

includes taxes & fees

Sep 21 - Sep 22

A rooftop pool with lounge chairs and potted plants, surrounded by modern buildings.

5. Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago

A refreshing seasonal escape awaits at this Chicago hotel's sun-drenched pool area.

￥38,853 total

includes taxes & fees

Sep 20 - Sep 21

An indoor swimming pool with lounge chairs and exercise equipment.

6. 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 center.

￥44,034 total

includes taxes & fees

Sep 27 - Sep 28

A modern indoor swimming pool with blue seating and a view of the city through large windows.

7. 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.

￥38,042 total

includes taxes & fees

Sep 27 - Sep 28

A large indoor swimming pool with clear blue water, surrounded by windows offering views of a cityscape.

8. Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

￥36,232 total

includes taxes & fees

Sep 27 - Sep 28

View all properties

Choose what matters most at hotels with a pool in Kenwood

Breakfast included

4 stars

Top Kenwood Hotel Reviews

Congress Plaza Hotel

10/10 Excellent

"Clean room, funky smell tho. Super nice staff. Very helpful"

Fairmont Chicago at Millennium Park

10/10 Excellent

"Stayed at the Fairmont Chicago and it exceeded every expectation. The rooms are spacious and clean, the staff make us feel welcome, and the location puts you steps from Millennium Park and the lakefront. Five stars — we'll be back."

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. The Chicago Hotel Collection Ambassador Gold Coast: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel: 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.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Kenwood on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Kenwood Hotels with a Pool

Our top choices for Kenwood hotels with a pool