
South Shore Vacations from $641
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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

The Whitehall Hotel, BW Premier Collection
Reviewed on Jun 17, 2026

Hotel Riu Plaza Chicago
Reviewed on Jun 21, 2026

Level Chicago Fulton Market
Reviewed on Jun 20, 2026

The Emily Hotel
Reviewed on Jun 21, 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
"It was a beautiful hotel, perfect location, parking was ok. Would definitely recommend staying again"
Reviewed on Jun 22, 2026

Hilton Chicago/Magnificent Mile Suites
"Nice property right near everything"
Reviewed on Jun 22, 2026

The Chicago Hotel Collection - Magnificent Mile
"The hotel was in a great location, and the staff were friendly and welcoming. My only complaint was that the hallway smelled like cigarettes and damp carpet. Overall, it was a pleasant stay, but the hallway and elevator odor could definitely be improved."
Reviewed on Jun 21, 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.

Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

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

Wendella's 90-min Chicago River Architecture Tour

























