The Best Hotels with a Pool in Near South Side, IL from NT$5,781 in 2026

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

Hyatt Regency McCormick Place Chicago : Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel : Hotel, 10-minute walk from University of Illinois Chicago. Provides a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access. The Chicago Hotel Collection Ambassador Gold Coast : Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. Hilton Chicago O'Hare Airport : Hotel, 2-minute walk from Grant Park. Features 2 restaurants, an indoor pool, and a health club.

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. Hilton Garden Inn Chicago McCormick Place

Near South Side

NT$5,781 total

includes taxes & fees

Aug 30 - Aug 31

2. Home2 Suites by Hilton Chicago McCormick Place

Near South Side

NT$5,820 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.

NT$6,467 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$6,142 total

includes taxes & fees

Aug 30 - Aug 31

5. Hilton Chicago

Downtown Chicago

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

NT$7,433 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$6,407 total

includes taxes & fees

Sep 8 - Sep 9

7. 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$6,902 total

includes taxes & fees

Sep 7 - Sep 8

8. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Slip into a vacation state of mind at Chicago's urban retreat with a sparkling indoor pool.

NT$5,834 total

includes taxes & fees

Sep 7 - Sep 8

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Breakfast included

4 stars

Top Near South Side Hotel Reviews

Hyatt Regency Chicago

10/10 Excellent

"Everything you need restaurant , rentals car in same place make so easy to do ,discount in dinner was great."

Frequently asked questions

What are some accommodations with pools in Near South Side?

Hyatt Regency McCormick Place Chicago: Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel: Hotel, 10-minute walk from University of Illinois Chicago. Provides a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access. The Chicago Hotel Collection Ambassador Gold Coast: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. Hilton Chicago O'Hare Airport: Hotel, 2-minute walk from Grant Park. Features 2 restaurants, an indoor pool, and a health club.

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 Northerly Island. 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

1. Hilton Garden Inn Chicago McCormick Place