
South Shore Vacations from $366
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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

La Banque Hotel
Reviewed on Jan 26, 2026

Hotel Riu Plaza Chicago
Reviewed on Jan 28, 2026

Trump International Hotel & Tower Chicago
Reviewed on Jan 24, 2026

Level Chicago – Old Town
Reviewed on Jan 18, 2026

Hotel Felix River North/Magnificent Mile
Reviewed on Jan 20, 2026
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
Yes perfectly clean
Reviewed on Jan 24, 2026

Embassy Suites by Hilton Chicago Downtown River North
Too few elevators working…
Reviewed on Jan 28, 2026

Hotel Riu Plaza Chicago
It was great!
Reviewed on Jan 25, 2026
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

Chicago Bulls Basketball Game at United Center
























