
South Shore Vacations from $335
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Your South Shore Vacation
Your next great escape is just around the corner with a vacation package to South Shore. Entertainment, relaxation and nonstop great times — you're bound to find it in this neighborhood. When it's time to see the sights, you'll find a lot of awesome attractions nearby including University of Chicago, Chicago Museum of Science and Industry and Robie House. Visit one, two or all during your trip to South Shore. Stop dreaming and start doing. When it's time to book your next vacation to South Shore, Expedia will help you get there.
The Latest South Shore Vacation Packages

Level Chicago – Old Town
Reviewed on Oct 22, 2025

Pendry Chicago
Reviewed on Oct 16, 2025

theWit Chicago, a Hilton Hotel
Reviewed on Oct 20, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on Oct 23, 2025

Level Chicago Fulton Market
Reviewed on Oct 15, 2025
Where to stay in South Shore

Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
South Shore Hotel Deals

Congress Plaza Hotel
Everything was good, good location and great value for money, shower was a bit inconsistent, sometimes it took a few minutes to heat up.
Reviewed on Oct 23, 2025

Holiday Inn Chicago Dwtn - The Mart by IHG
We didn’t know what to expect from a Holiday Inn in a tower and were pleasantly surprised. The building — hotel actually starts on the 15th floor — is like new and was very clean. The staff was universally friendly. The lobby floor has a grab-and-go food option available 24 hours and a nontraditional ...
Reviewed on Oct 20, 2025

Hilton Chicago/Magnificent Mile Suites
Great place to stay in the city!!! The room was super nice with an amazing city view and the end was just perfect !!! Housekeeping staff was outstanding and it was in a very downtown convenient area to walk and find everything around !!! Would come back for sure 10000%
Reviewed on Oct 23, 2025
Discover the most popular places to visit in South Shore

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do

Skydeck - Willis Tower Admission
