The Best Hotels with a Pool in Near South Side, IL from NT$5,402 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.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Near South Side Hotels with a Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Near South Side hotels with a pool

1. Hilton Garden Inn Chicago McCormick Place

Near South Side

NT$6,894 total

includes taxes & fees

Sep 8 - Sep 9

2. 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$7,005 total

includes taxes & fees

Sep 8 - Sep 9

3. Home2 Suites by Hilton Chicago McCormick Place

Near South Side

NT$6,951 total

includes taxes & fees

Sep 7 - Sep 8

4. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

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

NT$5,726 total

includes taxes & fees

Sep 8 - Sep 9

5. Hilton Chicago

Downtown Chicago

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

NT$7,300 total

includes taxes & fees

Sep 8 - Sep 9

6. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

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

NT$5,726 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$6,724 total

includes taxes & fees

Sep 10 - Sep 11

8. Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

NT$5,402 total

includes taxes & fees

Sep 7 - Sep 8

View all properties

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 Chicago

10/10 Excellent

"Na"

Hilton Chicago

10/10 Excellent

"I was upgraded to a larger room with amazing views upon request for my birthday weekend stay ! All of the staff were friendly and professional and Willie with housekeeping was especially helpful getting me an extra blanket and making some local recommendations for food and attractions. He was very kind and a real asset to the hotel staff . My server Juan in the 720 restaurant was also very nice . The breakfast buffet was excellent, a little pricey but includes all drinks including fresh OJ . The bacon and pancakes were delicious. I didn’t try the other restaurant Kittys . Only the rooms facing the street have views so keep that in mind when booking a room otherwise you’ll be facing a wall . The rooms are clean and beds are pretty comfortable . All in all a very good stay"

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.

Explore a world of travel with Expedia

Book Hotels in Near South Side on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Near South Side Hotels with a Pool

Our top choices for Near South Side hotels with a pool