South Shore Holidays from AU$2,160

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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.

Top Holiday Package Deals in South Shore

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was AU$2,657, price is now AU$2,160 per person
AU$2,160
per person
29 May - 1 June
found 1 day ago
Return direct flight included
Honolulu (HNL) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place

Reviewed on 25 Apr 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$5,108, price is now AU$3,902 per person
AU$3,902
per person
27 May - 1 June
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
Great location and value

Reviewed on 25 Apr 2026

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Price was AU$4,759, price is now AU$3,797 per person
AU$3,797
per person
27 May - 1 June
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.6/10 Exceptional! (3,950 reviews)
Very nice room. Pretty view and loved the window bench. Great location. Only ding is they have one elevator working for the entire hotel that takes forever. This is the second stay in 3 weeks and it still wasn’t repaired.

Reviewed on 26 Apr 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was AU$3,120, price is now AU$2,314 per person
AU$2,314
per person
29 May - 1 June
found 1 day ago
Return direct flight included
Honolulu (HNL) to Chicago (ORD)
9.2/10 Wonderful! (932 reviews)
We had a great time! Room was clean, spacious, and nice views! Staff was friendly and helpful. Will stay again

Reviewed on 26 Apr 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Price was AU$3,463, price is now AU$2,666 per person
AU$2,666
per person
29 May - 1 June
found 1 day ago
Return direct flight included
Honolulu (HNL) to Chicago (ORD)
9.2/10 Wonderful! (3,002 reviews)
Amazing location, great staff, room was luxurious, doormen were super friendly and helpful!

Reviewed on 24 Apr 2026

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

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.

Find hotels in Downtown Chicago

Our pick of the best South Shore Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$222 per night from 8 May to 9 May
AU$222
8 May - 9 May
includes taxes & fees
8/10 Very Good! (10,147 reviews)
There's NO PARKING! Parking lot next door charges $62 with no in/out privileges. We had to park 5 blocks away and it cost $30/24 hours. They say the have air conditioning in every room. It's "central" air conditioning and they control the temperature. Our room was uncomfortably warm.

Reviewed on 26 Apr 2026

Congress Plaza Hotel
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 28 Apr to 29 Apr
AU$185
28 Apr - 29 Apr
includes taxes & fees
8.2/10 Very Good! (2,645 reviews)
Loved the free breakfast and free drink! Front desk was extremely kind and helpful.

Reviewed on 26 Apr 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 25 May to 26 May
AU$196
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,136 reviews)
Stay was lovely, small room. I booked a king room and you could tell they put two twins together to make it a king but overall, very clean & loved the shower pressure!

Reviewed on 26 Apr 2026

River Hotel
See all 4,510 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
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beach holidays
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Frequently asked questions

How much does a South Shore holiday package cost?
Starting from an incredible AU$2,160, 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.

Discover the most popular places to visit in South Shore

Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$38
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

AU$56
per adult
92% of travellers recommend
Art Institute of Chicago
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.