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. Features 2 restaurants, an indoor pool, and a health club. Congress Plaza Hotel : Hotel, 5-minute walk from Chicago Riverwalk. Features 2 restaurants, an indoor pool, and a sauna. The Chicago Hotel Collection Ambassador Gold Coast : Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna.

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

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Check availability on Near South Side Hotels with a Pool

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Our top choices for Near South Side hotels with a pool

1. Hilton Garden Inn Chicago McCormick Place

Near South Side

CA $236 total

includes taxes & fees

Sep 2 - Sep 3

2. Home2 Suites by Hilton Chicago McCormick Place

Near South Side

CA $239 total

includes taxes & fees

Sep 2 - Sep 3

3. 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 $265 total

includes taxes & fees

Sep 2 - Sep 3

4. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

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

CA $258 total

includes taxes & fees

Sep 7 - Sep 8

5. Hilton Chicago

Downtown Chicago

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

CA $348 total

includes taxes & fees

Sep 7 - Sep 8

6. Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago

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

CA $262 total

includes taxes & fees

Sep 7 - Sep 8

Outdoor pool, cabanas (surcharge), pool umbrellas

7. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

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

CA $256 total

includes taxes & fees

Aug 30 - Aug 31

8. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Dive into modern bliss at this downtown hotel, where the indoor pool sparkles alongside skyline views.

CA $279 total

includes taxes & fees

Sep 7 - Sep 8

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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

Hyatt Regency O'Hare Chicago

10/10 Excellent

"Had a great time at the annual FanExpo. The skywalk was convenient but they closed it through the day which totally defeated the purpose. Great time otherwise."

InterContinental Chicago Magnificent Mile by IHG

8/10 Good

"Fantastic location, friendly and helpful staff, and very comfortable bedding (my friend who shared the room wtih me ordered the pillows for use at home!). Rooms are about the size one would expect for this neighborhood - smaller than in the suburbs! The bathroom amenities are high quality. I only subtracted a star because the elevators were very, very slow resulting in us and several other groups of guests using the stairs which were pretty poorly labeled for ease of use and for safety (if there had been an emergency. I gave this feedback to staff who were outwardly receptive - and who hopefully re-sign the stairwells so that other guests like us (and the other 8 people we found in them!) will know exactly where to go whether rushed or at a calm pace."

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. Features 2 restaurants, an indoor pool, and a health club. Congress Plaza Hotel: Hotel, 5-minute walk from Chicago Riverwalk. Features 2 restaurants, an indoor pool, and a sauna. The Chicago Hotel Collection Ambassador Gold Coast: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna.

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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Check availability on Near South Side Hotels with a Pool

Our top choices for Near South Side hotels with a pool

1. Hilton Garden Inn Chicago McCormick Place