South Side Luxury Holidays

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Top Luxury South Side Hotels

The Wheeler Mansion

The Wheeler Mansion

4 out of 5
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 ...
The Wheeler Mansion
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
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! (2,751 reviews)
"Nice location. Restaurants are just walking distance."

Reviewed on 14 Nov 2026

Best Western Grant Park Hotel
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
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 ...
Hyatt Regency McCormick Place Chicago
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.