South Chicago Holidays from AU$3,688

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Your South Chicago Holiday

South Chicago is calling! Whatever type of getaway you're organising, get ready to discover the best of this neighbourhood with a South Chicago holiday package. When it's time to get out and explore, you'll find lots of big-name attractions nearby including Calumet Park, Calumet Beach and Munson Beach. Visit one, two (or even all!) during your trip to South Chicago. Expedia is here to put your plans into action. Book your ideal South Chicago holiday today.

Top Holiday Package Deals in South Chicago

Price found within the past 48 hours. Click for updated prices.
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Price was AU$4,440, price is now AU$3,688 per person
AU$3,688
per person
28 Dec - 3 Jan
found 8 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.8/10 Excellent! (2,580 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was AU$7,537, price is now AU$5,906 per person
AU$5,906
per person
28 Dec - 3 Jan
found 8 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was AU$4,711, price is now AU$3,889 per person
AU$3,889
per person
28 Dec - 3 Jan
found 8 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was AU$4,555, price is now AU$3,773 per person
AU$3,773
per person
28 Dec - 3 Jan
found 8 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (2,419 reviews)
Great.

Reviewed on 10 Nov 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was AU$4,446, price is now AU$3,695 per person
AU$3,695
per person
28 Dec - 3 Jan
found 8 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Our guide on where to stay in South Chicago

Find the best South Chicago areas and neighborhoods for the activities you enjoy most. Learn more about South Chicago
A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Our pick of the best South Chicago 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$201 per night from 22 Nov to 23 Nov
AU$201
22 Nov - 23 Nov
includes taxes & fees
8/10 Very good! (10,171 reviews)
"Great stay!"

Reviewed on 11 Nov 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$199 per night from 2 Dec to 3 Dec
AU$199
2 Dec - 3 Dec
includes taxes & fees
8/10 Very good! (2,696 reviews)
"Very clean ans nice hotel"

Reviewed on 11 Nov 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is AU$183 per night from 10 Dec to 11 Dec
AU$183
10 Dec - 11 Dec
includes taxes & fees
8.8/10 Excellent! (5,614 reviews)
"Room was cleaned and nicely kept up. Convenient location and nice view of the river."

Reviewed on 10 Nov 2026

River Hotel
See all 4,243 properties in South Chicago
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
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Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a South Chicago holiday package cost?
Live it up in South Chicago from just AU$3,688. Choose from a wonderful selection of hotels, flights and rental cars to suit your travel style. You can score even more discounts when you add a few sightseeing activities to your holiday package.
How do I get a cheap travel package to South Chicago?
Combine your flights and hotels, toss in extras such as activities or a rental car, and save with a South Chicago holiday package. You won't just pick up impressive discounts on your escape — you'll have lots of choice within your reach too. When you book through Expedia, you can select from more than 550 partner airlines and 1 000 000 hotels around the globe. Your dream holiday starts right here, right now!
Where should I stay in South Chicago?
With so much to do in South Chicago, it's a good idea to secure a room in a hotel close to its attractions. Calumet Beach, Calumet Park and Bronzeville Childrens Museum are some interesting ones to put on your must-see list.
How far in advance should I book my South Chicago holiday?
While not all airlines release ticket prices early, it's usually possible to compare international fares on Expedia up to 12 months in advance. This is the time you can bag some fantastic bargains. If you're purchasing tickets last minute, you might get lucky. Sometimes the cheapest prices emerge just weeks before departure.
What does an Expedia South Chicago travel package include?
From hotels and flights to car rentals, Expedia can help you craft a South Chicago package that fits you. Heading away for a week or longer? Consider a flight, rental car and hotel bundle. If you're taking a quick break, a hotel and flight deal could suit you better. Tours and activities can be added after you've booked. Our packages make it a cinch to plan and save.
What should I know before booking a South Chicago travel package?
You'll save big with an Expedia travel package. Bundle your airfares, rental cars and hotels and pick up fantastic discounts. You're not restricted to hotels, though. We've got island resorts, cosy city apartments and everything in between!
Can I choose my airline with a South Chicago Expedia holiday package?
Yes, of course. Expedia has access to more than 550 airline partners around the world, so fly with the carrier that best fits your budget and travelling style.
If I'm not able to travel, can I cancel my South Chicago holiday package?
If your holiday plans in South Chicago have changed, it's good to know that it's possible to cancel your booking. If you made your booking less than 24 hours ago, you may be eligible for a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a cancellation fee. To find out more, check our Customer Service Portal.

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$58
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

AU$61
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
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.