South Chicago Holidays from AU$2,013

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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was AU$2,327, price is now AU$2,013 per person
AU$2,013
per person
26 Feb - 1 Mar
found 22 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Very clean room, friendly staff, wonderful breakfast!

Reviewed on 22 Jan 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was AU$3,201, price is now AU$2,822 per person
AU$2,822
per person
26 Feb - 1 Mar
found 23 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.

Reviewed on 11 Jan 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was AU$2,960, price is now AU$2,612 per person
AU$2,612
per person
26 Feb - 1 Mar
found 22 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
First time there. Staff was helpful and they provided excellent memorable service

Reviewed on 20 Jan 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was AU$2,389, price is now AU$2,110 per person
AU$2,110
per person
26 Feb - 1 Mar
found 22 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Everything about this hotel is special. Great staff- awesome restaurant/bar. Location is perfect. This hotel is my destination every time I come to the city. Which is quite often.

Reviewed on 20 Jan 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was AU$2,856, price is now AU$2,545 per person
AU$2,545
per person
26 Feb - 1 Mar
found 22 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Yes didn’t know you get free breakfast

Reviewed on 4 Jan 2026

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
Downtown Chicago featuring a city

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 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$235 per night from 14 Feb to 15 Feb
AU$235
14 Feb - 15 Feb
includes taxes & fees
8/10 Very Good! (9,790 reviews)
Really interesting place, great price for the location too. Staff was very friendly.

Reviewed on 19 Jan 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$267 per night from 1 Feb to 2 Feb
AU$267
1 Feb - 2 Feb
includes taxes & fees
8.4/10 Very Good! (2,541 reviews)
Great staff, good location .

Reviewed on 14 Jan 2026

Hilton Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$182 per night from 5 Feb to 6 Feb
AU$182
5 Feb - 6 Feb
includes taxes & fees
8.4/10 Very Good! (5,583 reviews)
Always a great stay, clean, great breakfast, great pool.

Reviewed on 22 Jan 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,525 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.
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beach holidays
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Frequently asked questions

How much does a South Chicago holiday package cost?
Live it up in South Chicago from just AU$2,013. 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.

Discover the most popular places to visit in South Chicago

Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(64 reviews)

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

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

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

Millennium Park
Chicago Riverwalk featuring a bay or harbour, a city and a river or creek

Chicago Riverwalk

4.5/5(26 reviews)

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

Chicago Riverwalk

Activities

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$37
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

AU$60
per adult
92% of travellers recommend
Art Institute of Chicago
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

AU$73
per adult
92% of travellers recommend
Chicago Crime and Mob Bus Tour
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.