The Best Hotels with a Pool in Woodlawn, IL from NT$5,638 in 2026

Q: What are some accommodations with pools in Woodlawn?

River Hotel : Hotel, 2-minute walk from Grant Park. Features 2 restaurants, an indoor pool, and a health club. The Chicago Hotel Collection Ambassador Gold Coast : Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel : Hotel, 8-minute walk from Lake Michigan. Offers complimentary wireless internet access, an indoor pool, and a 24-hour fitness center.

A wooden bridge over a calm river, surrounded by lush greenery and a distant building.

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Our top choices for Woodlawn hotels with a pool

1. Hilton Chicago

Downtown Chicago

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

NT$8,942 total

includes taxes & fees

Sep 27 - Sep 28

2. Hampton Inn Chicago West Loop Fulton Market Area

Downtown Chicago

Splash into urban relaxation at this West Loop hotel's stylish indoor pool, where sun loungers invite post-sightseeing unwinding.

NT$6,795 total

includes taxes & fees

Sep 27 - Sep 28

3. The Wade

Downtown Chicago

Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.

NT$5,638 total

includes taxes & fees

Sep 27 - Sep 28

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

4. Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago

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

NT$7,911 total

includes taxes & fees

Sep 20 - Sep 21

5. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

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

NT$9,294 total

includes taxes & fees

Oct 1 - Oct 2

6. Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, hot tub haven, and 24-hour fitness center.

NT$8,967 total

includes taxes & fees

Sep 27 - Sep 28

Indoor pool, open 7:00 AM to 10:00 PM, sun loungers

7. Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Splash into the city at this downtown hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.

NT$8,404 total

includes taxes & fees

Sep 20 - Sep 21

8. Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

NT$7,378 total

includes taxes & fees

Sep 27 - Sep 28

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Choose what matters most at hotels with a pool in Woodlawn

Breakfast included

4 stars

Top Woodlawn Hotel Reviews

Hilton Chicago

10/10 Excellent

"Very nice hotel in a great location! My first visit to Chicago and it was awesome! Hope to return soon and stay at the Hilton again."

Frequently asked questions

What are some accommodations with pools in Woodlawn?

River Hotel: Hotel, 2-minute walk from Grant Park. Features 2 restaurants, an indoor pool, and a health club. The Chicago Hotel Collection Ambassador Gold Coast: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel: Hotel, 8-minute walk from Lake Michigan. Offers complimentary wireless internet access, an indoor pool, and a 24-hour fitness center.

What is there to see and do in Woodlawn?

Explore places like Lake Michigan while you're in Woodlawn. The picturesque setting of Jackson Park and Bob-O-Link Meadow showcase the area's natural beauty.

When is the best time to book a hotel with a pool in Woodlawn?

You may want to consider an accommodation that offers an outdoor if you'll be visiting in the hottest 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 visit during the coldest months of January, February, or December when the average temp is 31°F.

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