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

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Pendry Chicago
theWit Chicago, a Hilton Hotel
Sable at Navy Pier Chicago, Curio Collection by Hilton
Level Chicago Fulton Market

Where to stay in South Shore

Find the best South Shore areas and neighborhoods for the activities you enjoy most. Learn more about South Shore

South Shore Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $168 total per night from Nov 9 to Nov 10
$168 total
Nov 9 - Nov 10
Total with taxes and fees
7.8/10 Good! (9,558 reviews)
Very Good
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

Congress Plaza Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
$139 nightly
The price is $163 total per night from Nov 23 to Nov 24
$163 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (1,948 reviews)
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

Holiday Inn Chicago Dwtn - The Mart by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $130 total per night from Nov 16 to Nov 17
$130 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (3,133 reviews)
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

Hilton Chicago/Magnificent Mile Suites
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.

Discover the most popular places to visit in South Shore

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.