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Cheap flights from Australia to Chicago Midway Airport from $715

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 15/10. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
18 Oct — 25 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Australia to Midway

Keep the following information in mind while searching for Australia to Midway flight deals. Data was last updated 18 September 2025.

Round-trip from

$1,520

One-way from

$715

Popular in

December

Cheapest in

March

Average price

$1,721
31/10-7/11
  • 31/10-7/11
  • 4 total stops
  • 74h 47m total
  • Australia to Chicago
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15/10
  • 15/10
  • 3 total stops
  • 38h 45m total
  • Australia to Chicago
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($667 potential increase over avg. return price).
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Cheapest flight prices on average. 4% potential price decrease ($107 potential savings vs. average return price).
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Average for round-trip flights in September 2025
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Find flight deals from Australia to Midway

Cheapest flights from Australia to Midway
Explore the most affordable flight options available from Australia to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 18 September 2025.

Fri 31/1011:20SYD - MDW
2 stops41h 17mMultiple Airlines
Fri 7/1106:30MDW - SYD
2 stops33h 30mMultiple Airlines
Deal found 16/9$1,520
Sat 1/1111:20SYD - MDW
2 stops41h 10mMultiple Airlines
Sat 15/1106:15MDW - SYD
2 stops33h 45mMultiple Airlines
Deal found 16/9$1,610
Tue 18/1110:40SYD - MDW
2 stops22h 58mDelta
Tue 25/1112:47MDW - SYD
2 stops26h 43mDelta
Deal found 17/9$2,072
Sat 8/1110:40SYD - MDW
2 stops24h 45mDelta
Sat 22/1109:41MDW - SYD
2 stops29h 49mDelta
Deal found 16/9$2,218
Tue 30/909:25SYD - MDW
2 stops23h 10mDelta
Wed 12/1112:47MDW - SYD
2 stops26h 43mDelta
Deal found 16/9$2,518
Tue 14/1010:25SYD - MDW
2 stops23h 18mDelta
Thu 23/1012:48MDW - SYD
2 stops26h 47mDelta
Deal found 16/9$2,593
Fri 31/1013:05SYD - MDW
1 stop20h 10mMultiple Airlines
Sun 2/1111:21MDW - SYD
2 stops27h 04mMultiple Airlines
Deal found 16/9$2,737
Fri 19/1210:40SYD - MDW
2 stops24h 38mDelta
Tue 30/1211:48MDW - SYD
2 stops26h 02mDelta
Deal found 15/9$2,779
Wed 24/1210:10MEL - MDW
2 stops24h 09mDelta
Sun 18/117:25MDW - MEL
2 stops45h 35mDelta
Deal found 17/9$3,011
Thu 13/1114:15MEL - MDW
2 stops23h 29mMultiple Airlines
Thu 20/1118:15MDW - MEL
1 stop41h 45mMultiple Airlines
Deal found 16/9$3,235
Thu 2/1009:45MEL - MDW
2 stops27h 13mMultiple Airlines
Fri 17/1005:10MDW - MEL
1 stop31h 50mMultiple Airlines
Deal found 16/9$3,876
Fri 10/1016:05MEL - MDW
1 stop23h 15mMultiple Airlines
Fri 24/1005:10MDW - MEL
2 stops33h 35mMultiple Airlines
Deal found 15/9$5,405

Cheapflights Fare Finder

 
Customise your flight search to find flights from Australia to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 647,157 searches. Data last updated 18 September 2025.
Use the filters below to find and compare flights from Australia to Chicago Midway Airport that are best for you.

Fly from

Australia

Fly to

Midway

Route

Depart

Return

Price

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 31/10

11:20-12:37

2 stops41h 17m

Chicago Midway

Fri 7/11

06:30-09:00

2 stops33h 30m

$1,520

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 1/11

11:20-12:30

2 stops41h 10m

Chicago Midway

Sat 15/11

06:15-09:00

2 stops33h 45m

$1,610

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 18/11

10:40-16:38

2 stops22h 58m

Chicago Midway

Tue 25/11

12:47-08:30

2 stops26h 43m

$2,072

MelbourneChicago

MEL - MDW

MELMDW

Melbourne

Fri 23/1

10:10-18:34

2 stops25h 24m

Chicago Midway

Sun 1/2

18:45-08:00

2 stops44h 15m

$2,143

MelbourneChicago

MEL - MDW

MELMDW

Melbourne

Fri 13/3

09:10-18:08

2 stops24h 58m

Chicago Midway

Fri 27/3

10:35-08:40

2 stops30h 05m

$2,218

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 8/11

10:40-18:25

2 stops24h 45m

Chicago Midway

Sat 22/11

09:41-08:30

2 stops29h 49m

$2,218

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 30/9

09:25-17:35

2 stops23h 10m

Chicago Midway

Wed 12/11

12:47-08:30

2 stops26h 43m

$2,518

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 8/10

10:25-18:25

2 stops24h 00m

Chicago Midway

Wed 29/10

10:40-07:10

2 stops28h 30m

$2,518

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 14/10

10:25-17:43

2 stops23h 18m

Chicago Midway

Thu 23/10

12:48-07:35

2 stops26h 47m

$2,593

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 31/10

09:40-17:55

2 stops24h 15m

Chicago Midway

Sun 2/11

10:40-08:30

2 stops28h 50m

$2,593

Flights are sorted by cheapest return flights first.

Deals found on 17/9

Showing 1-10 of 38 results
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Best time to book a flight from Australia to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Australia with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Australia to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Australia to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Australia to Chicago Midway Airport?

    For as low as $2,072, Delta can have you in Chicago Midway Airport from Australia in 22h 58m. The distance between Australia and Chicago Midway Airport is about 14861 km.

  • What are the most popular routes from Australia to Chicago Midway Airport?

    When deciding which route to take from Australia to Chicago Midway Airport, consider Sydney Kingsford Smith - Chicago Midway, Melbourne - Chicago Midway or Brisbane - Chicago Midway, as they are the most popular.

  • Can I find deals for flights from Australia to Midway that include hotel bookings?

    Yes. In addition to deals on Australia to Midway flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Australia to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Australia to Midway.

  • Can I find deals for business class flights from Australia to Midway?

    Yes. Cheapflights offers flight deals from Australia to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Why should you use Cheapflights to find cheap flight tickets from Australia to Midway?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Australia.

Can Cheapflights find flights from Australia to Midway with no change fees?

Certainly. Search results for flights to Midway from Australia shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Australia to Midway become cheaper?

Of course! You can now track prices for flights from Australia to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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