South Shore Holidays

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Your South Shore Holiday

Your next great escape is just around the corner with a holiday package to South Shore. Entertainment, relaxation and nonstop great times — you're bound to find it in this neighbourhood. 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 holiday to South Shore, Expedia will help you get there.

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
A busy city street with tall buildings, a bus, and cars.

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.

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A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

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A river with yellow boats, a bridge, and tall buildings.

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

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A wooden pavilion with a view of a city skyline and a body of water.

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.

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Our pick of the best South Shore Hotel Deals

River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
AU$265
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (5,459 reviews)
"Location was perfect. Staff were nice."

Reviewed on 16 Sept 2026

River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
AU$253
20 Sept - 21 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
AU$284
27 Sept - 28 Sept
includes taxes & fees
Congress Plaza Hotel
See all 4,311 properties in South Shore
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays
family friendly holidays
Family Friendly Holidays
Family Friendly Holidays
golf holidays
Golf Holidays
Golf Holidays
luxury holidays
Luxury Holidays
Luxury Holidays
romantic holidays
Romantic Holidays
Romantic Holidays
ski holidays
Ski Holidays
Ski Holidays
honeymoon holidays
Honeymoon Holidays
Honeymoon Holidays
pet friendly holidays
Pet-friendly Holidays
Pet-friendly Holidays
Spa Holidays
Spa Holidays
Spa Holidays

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.
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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.
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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.
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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.
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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.
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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.
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Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$38
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$56
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.