Luxury Holidays in South Side 2026

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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! (2,760 reviews)

"The air conditioner was leaking water and made half of the carpet wet and thus the room smelt bad as well."

Reviewed on 6 Aug 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 ...

See all 454 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.