The Best Hotels with a Pool in Near South Side, IL from NT$5,578 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. Congress Plaza Hotel : Hotel, 3-minute walk from Merchandise Mart. Provides 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. Hilton Chicago O'Hare Airport : Hotel, 10-minute walk from University of Illinois Chicago. Features a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access.

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

1. Home2 Suites by Hilton Chicago McCormick Place

Near South Side

NT$5,578 total

includes taxes & fees

Sep 1 - Sep 2

2. Hilton Garden Inn Chicago McCormick Place

Near South Side

NT$5,723 total

includes taxes & fees

Aug 30 - Aug 31

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.

NT$6,403 total

includes taxes & fees

Aug 30 - Aug 31

4. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

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

NT$6,005 total

includes taxes & fees

Aug 31 - Sep 1

5. Hilton Chicago

Downtown Chicago

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

NT$7,382 total

includes taxes & fees

Sep 7 - Sep 8

Seasonal outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

6. Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago

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

NT$6,364 total

includes taxes & fees

Sep 8 - Sep 9

7. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

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

NT$7,253 total

includes taxes & fees

Aug 31 - Sep 1

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.

NT$6,436 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

"The staff was very helpful! They were able to hold our bags after checkout since we had later flights."

Hilton Chicago

8/10 Good

"Waited a long time to check in. Loved the games in the lobby! Pool was great! Housekeeping didn’t clean our room on the second night- we came back to a dirty room with no sheets in a bed and the do not disturb sign was on the door. I called the front desk, but no one came so then I had to go track someone down in the hallway. We ended up waiting up at night to have someone come out sheets on the bed so we could go to sleep."

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. Congress Plaza Hotel: Hotel, 3-minute walk from Merchandise Mart. Provides 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. Hilton Chicago O'Hare Airport: Hotel, 10-minute walk from University of Illinois Chicago. Features a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access.

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. Home2 Suites by Hilton Chicago McCormick Place