South Shore Holidays
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Our guide on 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.
Magnificent Mile
An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Our pick of the best South Shore Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
NZ$368
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (5,433 reviews)
"Great location. Smallish rooms. Comfortable bed and clean bathroom. The only problem was; the elevators are split between top floors and bottoms floors. 2 elevators for 1-10 and 2 elevators for 11-38. There was one elevator out of order due to regular maintenance, according to the sign. It never ..."
Reviewed on 23 Sept 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
NZ$383
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (10,199 reviews)
"Very loud with nearby trains. Convenient location, beautiful lake view and a lovely old hotel, but needs to be updated with new bedding, a properly sized rug, and outlets for phones/tablets. Parking is $62 in an open parking lot. Staff was not friendly at check-in."
Reviewed on 23 Sept 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
NZ$390
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (2,313 reviews)
"Nice"
Reviewed on 23 Sept 2026
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 holiday 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 holiday 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?
Holiday Makers 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 holiday?
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 travelling 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 holiday 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 holiday.
If I'm not able to travel, can I cancel my South Shore holiday package?
We understand — sometimes life doesn't go according to plan. If you've booked a South Shore holiday 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 travels in Chicago. Stroll along the beaches or visit the shops while you're in the area.
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 enjoy a show at ETA Creative Arts Foundation during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
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 galleries.
Activities
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.