The Best Hotels with a Pool in Near South Side, IL from NT$5,869 in 2026

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

Hyatt Regency McCormick Place Chicago : Hotel steps from 875 North Michigan Avenue. Offers an indoor pool and flat-screen televisions. The Chicago Hotel Collection Ambassador Gold Coast : Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna. Omni Chicago Hotel : Hotel, 3-minute walk from Millennium Park. Provides a full-service spa, an indoor pool, and a 24-hour fitness center. Congress Plaza Hotel : Hotel, 10-minute walk from University of Illinois Chicago. Offers a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access. Hyatt Regency O'Hare Chicago : Hotel, 3-minute walk from Merchandise Mart. Features 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

Home2 Suites by Hilton Chicago McCormick Place

Near South Side

NT$5,869 total

includes taxes & fees

Aug 10 - Aug 11

Hilton Garden Inn Chicago McCormick Place

Near South Side

NT$6,403 total

includes taxes & fees

Aug 9 - Aug 10

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$6,249 total

includes taxes & fees

Aug 10 - Aug 11

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

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

NT$7,204 total

includes taxes & fees

Aug 13 - Aug 14

Sentral Michigan Avenue

Downtown Chicago

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

NT$6,370 total

includes taxes & fees

Aug 17 - Aug 18

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

Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago

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

NT$6,025 total

includes taxes & fees

Aug 9 - Aug 10

Hilton Chicago

Downtown Chicago

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

NT$10,962 total

includes taxes & fees

Aug 7 - Aug 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$7,786 total

includes taxes & fees

Aug 9 - Aug 10

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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

Congress Plaza Hotel

10/10 Excellent

"The porters were most helpful. The hotel was clean and well maintained. Being able to check on early was greatly helpful and the check out time of 12pm was greatly appreciated."

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"This was a great place to stay for a quick weekend trip. This was convenient to get to off the interstate and was so convenient to walk to all the shops along magnificent mile. Raymond was such a bright welcoming and the two valet drivers were great as well. They even let me keep my vehicle parked later than check out so we could explore some more of the city before we left town. I would stay here again. I wish we could have made it up to the rooftop bar but timing wasn’t our friend. Rooms were slightly outdated and I’ve stayed at places with softer sheets but I’m easy to please!"

Frequently asked questions

What are some accommodations with pools in Near South Side?

Hyatt Regency McCormick Place Chicago: Hotel steps from 875 North Michigan Avenue. Offers an indoor pool and flat-screen televisions. The Chicago Hotel Collection Ambassador Gold Coast: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna. Omni Chicago Hotel: Hotel, 3-minute walk from Millennium Park. Provides a full-service spa, an indoor pool, and a 24-hour fitness center. Congress Plaza Hotel: Hotel, 10-minute walk from University of Illinois Chicago. Offers a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access. Hyatt Regency O'Hare Chicago: Hotel, 3-minute walk from Merchandise Mart. Features 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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Our top choices for Near South Side hotels with a pool

Home2 Suites by Hilton Chicago McCormick Place