
South Shore Holidays from £1,279
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £335 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Your South Shore Holiday
Booking a South Shore holiday package is a superb way to become acquainted with this neighbourhood. From its well-known places to its lesser-known gems, there's plenty to discover. When it's time to sightsee, you'll find lots of awesome attractions nearby including University of Chicago, Chicago Museum of Science and Industry and Robie House. Visit one or all during your trip to South Shore. Expedia will help you turn your dream South Shore holiday into reality, whatever your budget or travel plans.


Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on 29 Mar 2026

Eurostars Magnificent Mile
Reviewed on 30 Mar 2026

Trump International Hotel & Tower Chicago
Reviewed on 29 Mar 2026

Pendry Chicago
Reviewed on 23 Mar 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.
Top hotels in South Shore

Congress Plaza Hotel
The hotel was not kept looking nice, very dinged up with peeling paint, bumpy carpet, and loose screws in locks. Looks like theyve tried to update and looks great in pictures. Staff wasnt rude but wasnt friendly either.
Reviewed on 30 Mar 2026

Hilton Chicago/Magnificent Mile Suites
yes
Reviewed on 30 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
Breakfast was cold and hotel got a bit noisy. The staff was friendly and rooms was a little ou
Reviewed on 30 Mar 2026
Frequently asked questions
Popular places to visit

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.

Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Things to do

Chicago: Navy Pier Centennial Wheel Ticket

Wendella's 90-min Chicago River Architecture Tour
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.














