Cheap Flights to Southwest Side

View AU$956 flight on Tue, 27 Jan 2026Opens in a new window

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Cheap Tickets to Southwest Side

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, 22 Jan - Wed, 4 Feb
SYD
Sydney
ORD
Chicago
AU$1,192 Return, found 6 hours ago
AU$1,192
Return
found 6 hours ago
Select Air Canada flight, departing Thu, 22 Jan from Sydney to Chicago, returning Wed, 4 Feb, priced at AU$1,192 found 6 hours ago
Qantas Airways
Tue, 20 Jan - Tue, 27 Jan
BNE
Brisbane
ORD
Chicago
AU$1,359 Return, found 11 hours ago
AU$1,359
Return
found 11 hours ago
Select Qantas Airways flight, departing Tue, 20 Jan from Brisbane to Chicago, returning Tue, 27 Jan, priced at AU$1,359 found 11 hours ago
American Airlines
Wed, 26 Aug - Wed, 2 Sept
SYD
Sydney
ORD
Chicago
AU$1,364 Return, found 5 days ago
AU$1,364
Return
found 5 days ago
Select American Airlines flight, departing Wed, 26 Aug from Sydney to Chicago, returning Wed, 2 Sept, priced at AU$1,364 found 5 days ago
Air New Zealand
Tue, 19 May - Tue, 26 May
MEL
Melbourne
ORD
Chicago
AU$1,499 Return, found 3 days ago
AU$1,499
Return
found 3 days ago
Select Air New Zealand flight, departing Tue, 19 May from Melbourne to Chicago, returning Tue, 26 May, priced at AU$1,499 found 3 days ago
United
Mon, 26 Jan - Tue, 3 Feb
SYD
Sydney
ORD
Chicago
AU$1,511 Return, just found
AU$1,511
Return
just found
Select United flight, departing Mon, 26 Jan from Sydney to Chicago, returning Tue, 3 Feb, priced at AU$1,511 just found

Find the cheapest month to fly from Columbus (CMH) to Chicago (MDW)

August is typically the cheapest month to fly

From AU$136 - AU$865 per traveller.

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Southwest Side Flights

Have the time of your life in Southwest Side

Flying to Southwest Side is now easier than ever when you use Expedia to book your trip. We’ve got an extensive catalogue of Southwest Side flight deals, giving you the greatest number of options to choose from. Whether you prefer to fly on weekdays or weekends, in the morning or at night, a quick search on Expedia.com.au will help you find cheap tickets to Southwest Side in seconds. We even make it simple for you to stick with a certain airline if you’re trying to rack up frequent flyer points.

Tips for flying and packing light

If it’s been a while since you’ve travelled, you might be due for a refresher when it comes to flying. That’s where our helpful blog, Out There Starts Here, comes in. Wondering whether to pack for fine dining or more casual eats? Or whether you really need to bring a jacket? Written by seasoned travel experts, the articles on our blog provide you with the latest details about certain destinations, so you know just what to expect. Check out some of our recent articles for the smartest ways to see the sights.

Fly for less when you bundle airfare and accommodation

Our already low airfares are even more affordable when you bundle your flights with a stay at one of the hotels in Southwest Side. By booking all of your travel plans with us, you’ll save time and money, and enjoy the convenience of having all of your arrangements in one place.

Get the power of planning in the palm of your hand

Booking your trip to Southwest Side, Chicago has never been easier than when you use our mobile app to plan your dream getaway. The Expedia App is available on both Android and iOS, allowing you to reserve flights and hotels at any time of day, no matter what kind of phone you use. You’ll also get exclusive offers, receive flight updates, and can earn extra points. Wherever you are, the Expedia App helps you get where you want to be.

Join the Expedia Rewards Program

If you enjoy the finer things in life, sign up for our rewards program to receive exclusive benefits when you book with us. Expedia Rewards opens the door to member-only deals, +VIP Access hotel benefits, and earning Expedia Rewards points, that you can redeem your way. You’ll also get access to Unreal Deals that could save you the price of a plane ticket to Southwest Side when bundled with your accommodation.

What are you waiting for?

Expedia.com.au helps you find cheap flights to Southwest Side AU$1,192. So why wait another second to begin planning your trip? Start your search right now, and you could be boarding the next Southwest Side-bound flight. Bon voyage!

Frequently asked questions

How do I find cheap flights to Southwest Side that have flexible change policies?
At Expedia, we've been channeling our inner gymnast to give you the most flexible airfares available. Simply click on "No change fee" directly below the filter heading "Flexible change policies" to find the best flights to Southwest Side.
Which airlines fly to Southwest Side?
With a great selection of airlines offering flights into or near Southwest Side, you have plenty of choice:

  • United Airlines - 12 950 flights to or near Southwest Side each month, including 12 950 flights to O'Hare Intl. Airport (ORD) per month.
  • American Airlines - 8 855 flights to or near Southwest Side each month, including 8 855 flights to O'Hare Intl. Airport (ORD) per month.
  • Delta Air Lines - 1 222 flights to or near Southwest Side each month, including 1 222 flights to O'Hare Intl. Airport (ORD) per month.

How can I find cheap tickets to Southwest Side?
One of the best ways to bag cheap tickets to Southwest Side is to be flexible with your travel dates. Search for your flights, then click "flexible dates" at the top of your results. It will reveal the cheapest prices for nearby days. The lowest price for a flight to Southwest Side in the last seven days was AU$1,192. Booking well in advance will generally help you get an even bigger bargain.
How much is a flight to Southwest Side?
If you were flying one way from Brisbane (BNE), you could've locked in an affordable ticket for just AU$956 in the last seven days. Round-trip journeys to Southwest Side ranged from only AU$1,192 to AU$1,511 during this same period.
What are the most popular airports to fly into in Southwest Side?
Pack your bags and jet into O'Hare Intl. Airport (ORD), Southwest Side's primary flight hub. Secure a seat on one of the 25 318 flights that land at this favourite destination every month.
When is the cheapest time to fly to Southwest Side?
If you'd rather spend your hard-earned holiday money getting to know Southwest Side rather than on getting there, depart earlier in the week. The most affordable day to travel is normally Tuesday, with Monday running a close second. With many people keeping their travel to weekends, Saturday often has the costliest ticket prices.
How much is a plane ticket to Southwest Side?
Seats to Southwest Side ranged from AU$1,192 to AU$1,511 in the last seven days. Usually, the sooner you book the better the price.
What months are the cheapest to book a flight to Southwest Side?
February is the best month to secure a seat for your Southwest Side holiday. Airfares are at their most expensive throughout the busy month of December, so keep clear of this time if you can.
Flights to Southwest Side information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Return price
AU$1,191

Trending flights to Southwest Side

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, 22 Jan - Wed, 4 Feb
SYD
Sydney
ORD
Chicago
AU$1,192 Return, found 6 hours ago
AU$1,192
Return
found 6 hours ago
Select Air Canada flight, departing Thu, 22 Jan from Sydney to Chicago, returning Wed, 4 Feb, priced at AU$1,192 found 6 hours ago

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