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 4-star luxury hotel in Chicago. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Soldier Field and Grant Park are located ...
10/10 Exceptional! (1 review)
"A unique place to stay near the convention centre."

Reviewed on 23 Jun 2025

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 ...
8/10 Very Good! (2,546 reviews)
"I really loved the bakery next door. Parking was pretty convenient. Room was clean. Only downside is balcony on 3rd floor was closed, and the gym wasn’t up to par."

Reviewed on 1 Jul 2025

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 4-star eco-certified hotel in Chicago. Enjoy free Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,008 reviews)
"Clean, modern rooms"

Reviewed on 28 Jun 2025

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.