
South Shore Vacations from $239
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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

Hotel Riu Plaza Chicago
Reviewed on Jan 9, 2026

Level Chicago – Old Town
Reviewed on Dec 25, 2025

Hotel Felix River North/Magnificent Mile
Reviewed on Jan 7, 2026


Trump International Hotel & Tower Chicago
Reviewed on Jan 3, 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

Hilton Chicago
Staff members were friendly and helpful. Great location walking distance and transportation options.
Reviewed on Jan 9, 2026

Hilton Chicago/Magnificent Mile Suites
Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ...
Reviewed on Jan 7, 2026

Palmer House a Hilton Hotel
This stay was perfection from beginning to end. Totally wonderful experience in every way.
Reviewed on Jan 9, 2026
Discover the most popular places to visit in South Shore

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.

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

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

Skydeck - Willis Tower Admission

Chicago Bulls Basketball Game at United Center























