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
Downtown Chicago
Save 100% on your flight
Price was $640, price is now $335 per person
$335
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
We booked a two-bedroom corner suite which was very spacious (especially the kitchen/living room area), and we had very good view of the old town overlooking from the big porch. The location of the hotel was pretty nice, only 15 min to Michigan Avenue.
However, a few things were disappointing: 1) The check-in process was longer than expected which took 15-20 min to get the room keys; 2) The floor of the suite was quite dusty and the door of the master bedroom was broken (could not be locked); 3) The room phone didn't work at all and we had to use our phone to call the hotel front desk to ask questions; 4) This was the one and only hotel we'd stayed worldwide that did not provide foam pillows (feather pillows only to which one of our family members was allergic).
Reviewed on Oct 22, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $707, price is now $360 per person
$360
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on Oct 16, 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $928, price is now $478 per person
$478
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on Oct 20, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $984, price is now $529 per person
$529
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,188 reviews)
Everything was amazing. I will definitely be back!
Reviewed on Oct 23, 2025
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,045, price is now $589 per person
$589
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (324 reviews)
Fully furnished kitchen, our room wasn’t ready when we checked in @330p but they gave us another room that was available!!
Reviewed on Oct 15, 2025
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
Downtown Chicago
5 out of top 10 points of interest in this area
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
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
Holiday Inn Chicago Dwtn - The Mart by IHG
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
Hilton Chicago/Magnificent Mile Suites
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
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
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(332 reviews)
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
4.5/5(4,870 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.