The Best Hotels with a Pool in Near South Side, IL 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. Features 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel : Hotel steps from 875 North Michigan Avenue. Offers an indoor pool and flat-screen televisions. The Chicago Hotel Collection Ambassador Gold Coast : Hotel, 10-minute walk from University of Illinois Chicago. Provides a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access. Hyatt Regency O'Hare Chicago : 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$5,797 total

includes taxes & fees

Aug 30 - Aug 31

2. Home2 Suites by Hilton Chicago McCormick Place

Near South Side

NT$5,836 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$6,485 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$6,159 total

includes taxes & fees

Aug 31 - Sep 1

5. Sentral Michigan Avenue

Downtown Chicago

Indoor pool oasis at upscale Michigan Avenue aparthotel offers year-round swimming enjoyment.

NT$6,973 total

includes taxes & fees

Sep 2 - Sep 3

6. Hilton Chicago

Downtown Chicago

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

NT$7,432 total

includes taxes & fees

Sep 7 - Sep 8

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

7. Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago

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

NT$6,100 total

includes taxes & fees

Sep 7 - Sep 8

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$6,173 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

The Chicago Hotel Collection - Magnificent Mile

8/10 Good

"Good for the price"

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. Features 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel: Hotel steps from 875 North Michigan Avenue. Offers an indoor pool and flat-screen televisions. The Chicago Hotel Collection Ambassador Gold Coast: Hotel, 10-minute walk from University of Illinois Chicago. Provides a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access. Hyatt Regency O'Hare Chicago: 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 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.

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

1. Hilton Garden Inn Chicago McCormick Place