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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

Stay at this luxury hotel in Chicago. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Soldier Field and Grant Park are located ...

Best Western Grant Park Hotel

1100 S Michigan Ave Chicago IL

14 min drive from University of Chicago

Stay at this hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...

8.2/10 Very Good! (2,729 reviews)

"Our suite was not ready by check in time. Finally, got into room after telling front desk we would be asking to cancel reservation and get full refund. One of the two elevators did not work. Room & hotel was old and dated. Our pull out sofa bed also had a disgusting stain on it. Would never stay ..."

Reviewed on 22 Jun 2026

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr Chicago IL

11 min drive from University of Chicago

Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...

9.2/10 Wonderful! (1,141 reviews)

"So I had gotten free parking with my room which wasn’t free at all the Hotel says it’s free but the parking garage says otherwise pretty much the parking attendance give you a hard time with no help and your forced to pay to leave only complaint I had about it the hotel."

Reviewed on 21 Jun 2026

See all 472 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.