South Side Beach Vacations
Book a Beach 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*
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Top Beach vacation packages in South Side
Price found within the past 48 hours. Click for updated prices.
4 Night Beach vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Top Beach South Side Hotels
The Wheeler Mansion
2020 South Calumet Avenue Chicago IL
- 11 min drive from University of Chicago
Stroll along the shore in Chicago, as you'll be near the beach with a holiday at this luxury, boutique hotel. Amenities at The Wheeler Mansion include a ...
9.6/10 Exceptional! (8 reviews)
"Awesome stay. Close to Soldiers Field."
Reviewed on Sep 3, 2026
Marriott Marquis Chicago
2121 South Prairie Avenue Chicago IL
- 11 min drive from University of Chicago
Enjoy your stay at this hotel and enjoy the sunsets on the beach in Chicago, as you'll be close to the beach. Amenities at Marriott Marquis Chicago include 9 ...
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
- 11 min drive from University of Chicago
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
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
￥3,886
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.
