South Side Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Luxury vacation packages in South Side
Price found within the past 48 hours. Click for updated prices.
4 Night Luxury vacations in South Side
Price found within the past 48 hours. Click for updated prices.
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 ...
9.6/10 Exceptional! (8 reviews)
"Awesome stay. Close to Soldiers Field."
Reviewed on Sep 3, 2026
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! (2,727 reviews)
"The gym was non existent."
Reviewed on Sep 29, 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! (1,473 reviews)
"Lit"
Reviewed on Sep 30, 2026
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.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,853
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
