Book the Best Hotels with POOL in Near South Side in 2026

Q: What are some accommodations with pools in Near South Side?

Hyatt Regency McCormick Place Chicago : Hotel, 2-minute walk from Grant Park. Offers 2 restaurants, an indoor pool, and a health club. River 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. Provides complimentary wireless internet access, an indoor pool, and a 24-hour fitness center.

An aerial view of a circular plaza with a central monument, surrounding pathways, and a waterfront.

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Our top choices for Near South Side hotels with a pool

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.

1. Hilton Garden Inn Chicago McCormick Place

Near South Side

CA $382 total

includes taxes & fees

Oct 23 - Oct 24

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

Near South Side

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

CA $382 total

includes taxes & fees

Oct 23 - Oct 24

3. Home2 Suites by Hilton Chicago McCormick Place

Near South Side

CA $390 total

includes taxes & fees

Oct 15 - Oct 16

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

4. Hilton Chicago

Downtown Chicago

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

CA $394 total

includes taxes & fees

Oct 12 - Oct 13

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

5. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

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

CA $414 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.

6. 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 $249 total

includes taxes & fees

Sep 27 - Sep 28

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

7. Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago

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

CA $339 total

includes taxes & fees

Sep 27 - Sep 28

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

8. 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.

CA $343 total

includes taxes & fees

Sep 27 - Sep 28

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Choose what matters most at hotels with a pool in Near South Side

Breakfast included

4 stars

Top Near South Side Hotel Reviews

Hilton Chicago

10/10 Excellent

"Rooms are large and very clean. Has a refrigerator, but no microwave."

The Chicago Hotel Collection - Magnificent Mile

8/10 Good

"Stayed in a junior suite !! Very nice until the A/C broke (97* outside) had to drag all of our stuff back to the lobby just to get another room !! When, they should have come up and given us the key to the new room !! Next (2) days in the the room we had no hot water in the morning to take a shower so the next three days were cold showers in the morning (very annoying). I would love to stay there again but I’m not so sure."

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent

"The hotel needs remodeling, but it was truly a wonderful stay. We had a comfortable bed, an air conditioned room, and the most helpful staff. It would have been nice to have more updated elevators, and for the breakfast to be with real plates, cups, and utensils. But otherwise, we really enjoyed the centralized location and comfortable suite."

Frequently asked questions

What are some accommodations with pools in Near South Side?

Hyatt Regency McCormick Place Chicago: Hotel, 2-minute walk from Grant Park. Offers 2 restaurants, an indoor pool, and a health club. River 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. Provides complimentary wireless internet access, an indoor pool, and a 24-hour fitness center.

What is there to see and do in Near South Side?

Explore places like Soldier Field and Lake Michigan while you're in Near South Side. Surround yourself with nature at Grant Park and Burnham Park. Travelers love Near South Side for its array of dining options.

When is the best time to book a hotel with a pool in Near South Side?

You may want to consider an accommodation with an outdoor swimming pool if you'll be visiting 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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Our top choices for Near South Side hotels with a pool