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Top Luxury South Side Hotels

The Wheeler Mansion

2020 South Calumet Avenue Chicago IL

11 min drive from University of Chicago

Choose luxury at The Wheeler Mansion, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. The lounge bar, terrace, and garden are ...

Best Western Grant Park Hotel

1100 S Michigan Ave Chicago IL

14 min drive from University of Chicago

Spoil yourself with a luxury vacation in Chicago. Popular amenities include a restaurant and a 24-hour fitness center.

8.2/10 Very Good! (2,753 reviews)

"It was a pretty poor experience. The first night was by far the worst, as we found a bug crawling on the bed, which the sheets felt dirty and old. The walls were very thin. We could hear people from down the hall, and it felt like there was no privacy. The workers were either decent or creepy. There ..."

Reviewed on Jul 13, 2026

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr Chicago IL

11 min drive from University of Chicago

Choose luxury at Hyatt Regency McCormick Place Chicago , where you can enjoy amenities like pillowtop beds, designer toiletries, and more. The 2 bars, 24-hour ...

9.2/10 Wonderful! (1,203 reviews)

"Property was laid out nicely and in a great location. Checking in was very quick and the people at the front desk were very courteous and helpful. Room was cleaned up daily and I had a great stay."

Reviewed on Jul 13, 2026

See all 458 properties in South Side

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.