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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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 $249 total

includes taxes & fees

Sep 1 - Sep 2

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

2. Home2 Suites by Hilton Chicago McCormick Place

Near South Side

CA $252 total

includes taxes & fees

Sep 1 - Sep 2

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 $278 total

includes taxes & fees

Sep 1 - Sep 2

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 $247 total

includes taxes & fees

Sep 7 - Sep 8

An indoor swimming pool with a view of a brick building through large windows. There are seating areas with tables and chairs.

5. Hilton Chicago

Downtown Chicago

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

CA $347 total

includes taxes & fees

Sep 7 - Sep 8

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

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

An indoor swimming pool with lounge chairs and a no diving sign.

7. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Chicago hotel offers refreshing stays with indoor pool, fitness centre, and walkable Michigan Avenue access.

CA $289 total

includes taxes & fees

Aug 31 - Sep 1

A swimming pool with lounge chairs and a wall with a patterned design.

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 $278 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

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent

"excellent stay! awesome staff!"

Hilton Chicago

8/10 Good

"The location of this hotel is incredible, and the amenities were great (very nice gym, pool, etc…all in good order). A few frustrations with our stay, housekeeping didn’t visit at all 2 of the 4 days we were there and we needed to contact the desk for towels etc… Also the street noise was VERY loud at night, especially on weekend nights. Highly recommend earplugs to sleep with. Staff were all nice and friendly. Although there were staff in the lobby trying to stop and sell everyone some sort of Hilton timeshare (that was kind of annoying). We will be happy to stay again, but will bring earplugs (and better pillows) for our next stay."

The Royal Sonesta Chicago Downtown

8/10 Good

"Nice place. Great location. One thing that did annoy me. They put a 100.00 hold on my card for every night I was there (three nights -300.00). I asked them when I would be reimbursed and they told me in 5-7 business days. I thought the purpose of giving them your CC was so they could charge the card at the end of the visits. Now they basically steal your money for the length of your visit. Here’s the math. They have 381 guest room. Assume they are full. Average length of stay is 3 night. 381x300 equals 114,300.00 that they get to hold for a week plus. Royal Sonesta is a chain of over 1000 hotels. Now they are holding 114m of our money (rough math). At a 9 % return, the parent company makes 10 million plus on our temporary invested. Kind of tired of getting screwed at every opportunity."

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