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. Features 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel : 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 poolside seating area with chairs, and large windows offering views of the outside.

1. 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 $271 total

includes taxes & fees

Nov 2 - Nov 3

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.

2. Home2 Suites by Hilton Chicago McCormick Place

South Loop

CA $257 total

includes taxes & fees

Nov 1 - Nov 2

A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a view of a building through large windows.

3. Hilton Garden Inn Chicago McCormick Place

South Loop

CA $269 total

includes taxes & fees

Nov 2 - Nov 3

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.

CA $214 total

includes taxes & fees

Nov 9 - Nov 10

5. Hilton Chicago

Downtown Chicago

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

CA $322 total

includes taxes & fees

Oct 30 - Oct 31

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 $215 total

includes taxes & fees

Nov 12 - Nov 13

A swimming pool with lounge chairs and a lifeguard chair, surrounded by a fence, with tall buildings in the background.

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 $267 total

includes taxes & fees

Nov 11 - Nov 12

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

8. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

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

CA $218 total

includes taxes & fees

Nov 1 - Nov 2

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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

The Wade

10/10 Excellent

"Loved this trendy hotel. Great location, amenities, and service."

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. Features 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel: 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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