Plan, book, travel with confidence
Better together
Save up to ￥109,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

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! (2,696 reviews)

The rooms are nothing as what is described on Expedia. The front staff were extremely rude and unhelpful. The amenities Expedia claims the hotel has is false.

Reviewed on May 6, 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! (1,070 reviews)

Really nice and super clean

Reviewed on May 6, 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.