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Cheap flights from Australia to Chicago Midway Airport from $1,180

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 19/11. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
4 Dec — 11 Dec1
1 adult
1 adult, Economy, 0 bags

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 4 November 2025.

Round-trip from

$1,530

One-way from

$1,180

Popular in

December

Cheapest in

March

Average price

$1,765
8/12-31/12
  • 8/12-31/12
  • 4 total stops
  • 72h 14m total
  • Australia to Chicago
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19/11
  • 19/11
  • 3 total stops
  • 51h 08m total
  • Australia to Chicago
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($627 potential increase over avg. return price).
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Cheapest flight prices on average. 4% potential price decrease ($99 potential savings vs. average return price).
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Average for round-trip flights in November 2025
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Find flight deals from Australia to Midway

Enter your travel dates to find the best prices.

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 4 November 2025.

Mon 8/1211:20SYD - MDW
2 stops38h 26mMultiple Airlines
Wed 31/1206:12MDW - SYD
2 stops33h 48mMultiple Airlines
Deal found 3/11$1,530
Wed 5/1111:05BNE - MDW
2 stops22h 38mDelta
Sun 9/1119:02MDW - BNE
2 stops45h 18mDelta
Deal found 3/11$1,572
Sun 7/1217:45SYD - MDW
2 stops33h 07mMultiple Airlines
Wed 31/1206:12MDW - SYD
2 stops33h 48mMultiple Airlines
Deal found 3/11$1,615
Sun 23/1110:40SYD - MDW
2 stops30h 00mDelta
Sun 30/1109:41MDW - SYD
2 stops29h 49mDelta
Deal found 2/11$1,737
Thu 25/1210:40SYD - MDW
2 stops23h 39mDelta
Thu 22/113:49MDW - SYD
2 stops25h 41mDelta
Deal found 3/11$2,168
Sun 21/1210:40SYD - MDW
2 stops23h 39mDelta
Sat 10/111:45MDW - SYD
2 stops27h 45mDelta
Deal found 1/11$2,562
Sat 20/1210:40SYD - MDW
2 stops28h 42mDelta
Fri 2/111:48MDW - SYD
2 stops27h 42mDelta
Deal found 3/11$3,203
Sun 14/1210:40SYD - MDW
2 stops30h 07mDelta
Fri 2/111:48MDW - SYD
2 stops27h 42mDelta
Deal found 3/11$3,560
Sun 28/1223:55MEL - MDW
2 stops37h 50mMultiple Airlines
Thu 8/107:00MDW - MEL
1 stop29h 00mMultiple Airlines
Deal found 2/11$3,656
Wed 17/1210:40SYD - MDW
2 stops30h 07mDelta
Wed 24/1206:00MDW - SYD
2 stops33h 30mDelta
Deal found 2/11$3,676
Wed 17/1210:10MEL - MDW
2 stops30h 37mDelta
Wed 24/1209:50MDW - MEL
2 stops29h 10mDelta
Deal found 3/11$4,008
Thu 6/1108:35BNE - MDW
2 stops29h 39mMultiple Airlines
Tue 11/1106:00MDW - BNE
2 stops32h 20mMultiple Airlines
Deal found 3/11$8,865

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 4 November 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

Mon 8/12

11:20-08:46

2 stops38h 26m

Chicago Midway

Wed 31/12

06:12-09:00

2 stops33h 48m

$1,530

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 7/12

17:45-09:52

2 stops33h 07m

Chicago Midway

Wed 31/12

06:12-09:00

2 stops33h 48m

$1,615

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 23/11

10:40-23:40

2 stops30h 00m

Chicago Midway

Sun 30/11

09:41-08:30

2 stops29h 49m

$1,737

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 25/12

10:40-17:19

2 stops23h 39m

Chicago Midway

Thu 22/1

13:49-08:30

2 stops25h 41m

$2,168

MelbourneChicago

MEL - MDW

MELMDW

Melbourne

Fri 13/3

09:10-18:08

2 stops24h 58m

Chicago Midway

Fri 27/3

14:00-08:40

2 stops26h 40m

$2,223

MelbourneChicago

MEL - MDW

MELMDW

Melbourne

Wed 11/3

09:10-18:34

2 stops25h 24m

Chicago Midway

Sun 15/3

13:05-07:00

2 stops49h 55m

$2,524

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 21/12

10:40-17:19

2 stops23h 39m

Chicago Midway

Sat 10/1

11:45-08:30

2 stops27h 45m

$2,562

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 14/12

10:40-23:47

2 stops30h 07m

Chicago Midway

Fri 2/1

11:48-08:30

2 stops27h 42m

$3,560

MelbourneChicago

MEL - MDW

MELMDW

Melbourne

Sun 28/12

23:55-20:45

2 stops37h 50m

Chicago Midway

Thu 8/1

07:00-05:00

1 stop29h 00m

$3,656

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 17/12

10:40-23:47

2 stops30h 07m

Chicago Midway

Wed 24/12

06:00-08:30

2 stops33h 30m

$3,676

Flights are sorted by cheapest return flights first.

Deals found on 2/11

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 $1,737, Delta can have you in Chicago Midway Airport from Australia in 30h. 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 Melbourne - Chicago Midway, Sydney Kingsford Smith - 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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