South Shore Vacations
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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
4 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.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).
South Shore Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
NT$3,707
NT$4,407 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very Good! (10,283 reviews)
"Stay was fine. I’d love to leave five stars but I have been asking why I was charged an additional 104 usd to my credit card after we left via hotels.com chat and emailing the hotel directly but they have yet to respond. Hoping this gets me a reply and I can update my review"
Reviewed on 2026/8/10
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
NT$4,619
NT$5,491 total
Aug 30 - Aug 31
includes taxes & fees
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
NT$5,782
NT$7,908 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (2,750 reviews)
"It was nice"
Reviewed on 2026/8/10
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.
Frequently asked questions
How much does a South Shore vacation package cost?
Starting from an incredible , you can handcraft your own South Shore package. Simply combine flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to South Shore?
Just think of all the awesome things you could do in South Shore with a pile of extra cash in your wallet. Watch your savings stack up when you combine your travel bookings into a South Shore vacation package. You have plenty of choice when it comes to booking with Expedia too. In fact, you can select from over 550 air carriers and 1,000,000 hotel options globally. Whether you're enjoying a break with the entire family or going it alone, exploring South Shore is better with a package.
Where should I stay in South Shore?
Vacationers come from far and wide to experience University of Chicago and Chicago Museum of Science and Industry in South Shore. Stay within walking distance of these fantastic attractions and visit them whenever you please.
How far in advance should I book my South Shore vacation?
Search Expedia to compare international fares as soon as possible. You can usually purchase a seat up to 12 months before departure. If you can't see your preferred air carrier, or you have to book last minute, don't despair. Cheap tickets to South Shore sometimes emerge a few weeks before departure.
What does an Expedia South Shore travel package include?
That depends on what you want. If you're traveling solo, you might decide to combine flights and hotels. Bringing the whole family to South Shore? A travel package including hotels, flights and rental cars might suit you better. Expedia gives you the freedom and flexibility to tailor-make your travel package.
What should I know before booking a South Shore travel package?
You'll save plenty with an Expedia travel package. Bundle your airfares, rental cars and hotels and score fantastic discounts. Hotels aren't your only option, however. We have island resorts, creek-side mountain cabins and even treehouses and ranches!
Can I choose my airline with a South Shore Expedia vacation package?
Expedia has access to more than 550 partner airlines worldwide, so you sure can! Simply select the carrier you want and put together your ideal South Shore vacation.
If I'm not able to travel, can I cancel my South Shore vacation package?
We understand — sometimes life doesn't go according to plan. If you've booked a South Shore vacation package and have to amend or cancel it, we can help. It's always worth checking out our Customer Service Portal first for information. But in general, if you've taken out your package within 24 hours, you may be able to cancel or change your itinerary at no cost. If it's been longer than 24 hours, your airline, hotel or car rental company may impose a charge.
Stay near popular South Shore attractions
Rainbow Beach
Why not spend a lazy afternoon at Rainbow Beach during your trip to Chicago? Stroll along the beaches or visit the shops while you're in the area.
South Shore Cultural Center
Enjoy an outing to South Shore Cultural Center during your stay in Chicago. Amble around the area's beaches or visit its shops.
Stony Island Arts Bank
You can spend time exploring the galleries in Stony Island Arts Bank during your trip to Chicago. Stroll along the beaches or visit the shops while you're in the area.
South Shore Golf Course
Enjoy a round of golf in Chicago at South Shore Golf Course. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
Arthur Ashe Beach
Why not spend a lazy afternoon at Arthur Ashe Beach during your trip to Chicago? Stroll along the beaches or visit the shops while you're in the area.
ETA Creative Arts Foundation
You can make plans for a show at ETA Creative Arts Foundation during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.