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Cheap flights from Australia to Chicago Midway Airport from $1,048

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 29/1. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
22 Dec — 29 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 22 November 2025.

Round-trip from

$2,154

One-way from

$1,048

Popular in

December

Cheapest in

March

Average price

$1,788
Delta
  • Delta
  • 15/1-31/1
  • 4 total stops
  • 48h 18m total
  • Australia to Chicago
Search Deals
29/1
  • 29/1
  • 2 total stops
  • 43h 59m total
  • Australia to Chicago
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($635 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($98 potential savings vs. average return price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 22 November 2025.

Thu 25/1214:15SYD - MDW
2 stops35h 50mDelta
Tue 13/111:21MDW - SYD
2 stops26h 29mDelta
Deal found 19/11$2,383
Sat 27/1210:40SYD - MDW
2 stops23h 39mDelta
Mon 12/113:28MDW - SYD
2 stops26h 02mDelta
Deal found 19/11$2,459
Thu 4/1210:40SYD - MDW
2 stops30h 07mDelta
Mon 8/1206:00MDW - SYD
2 stops33h 30mDelta
Deal found 21/11$2,521
Fri 26/1210:40SYD - MDW
2 stops47h 46mDelta
Sat 10/113:28MDW - SYD
2 stops26h 02mDelta
Deal found 19/11$2,761
Mon 29/1210:40SYD - MDW
2 stops23h 39mDelta
Mon 5/119:16MDW - SYD
2 stops42h 34mDelta
Deal found 19/11$2,785
Wed 10/1211:05BNE - MDW
2 stops28h 42mDelta
Fri 2/111:48MDW - BNE
2 stops28h 32mDelta
Deal found 20/11$2,823
Mon 29/1210:40SYD - MDW
2 stops23h 39mDelta
Sun 4/109:50MDW - SYD
2 stops28h 00mDelta
Deal found 19/11$2,860
Mon 29/1210:40SYD - MDW
2 stops39h 25mDelta
Sat 3/116:25MDW - SYD
2 stops45h 25mDelta
Deal found 19/11$3,076
Wed 17/1211:05BNE - MDW
2 stops40h 53mDelta
Mon 5/113:49MDW - BNE
2 stops26h 31mDelta
Deal found 20/11$3,386
Sun 14/1210:40BNE - MDW
2 stops23h 38mDelta
Mon 5/109:50MDW - BNE
2 stops30h 30mDelta
Deal found 20/11$3,460
Fri 12/1210:40BNE - MDW
2 stops23h 38mDelta
Fri 2/111:48MDW - BNE
2 stops28h 32mDelta
Deal found 20/11$3,536
Mon 29/1209:55SYD - MDW
2 stops27h 50mMultiple Airlines
Sun 4/108:00MDW - SYD
1 stop29h 55mMultiple Airlines
Deal found 19/11$3,572

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 22 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

Thu 15/1

10:40-16:29

2 stops22h 49m

Chicago Midway

Sat 31/1

13:26-06:50

2 stops24h 24m

$2,154

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 12/2

10:40-17:45

2 stops24h 05m

Chicago Midway

Thu 26/2

12:46-06:50

2 stops25h 04m

$2,158

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 2/2

10:40-17:29

2 stops23h 49m

Chicago Midway

Thu 19/2

13:28-08:30

2 stops26h 02m

$2,158

MelbourneChicago

MEL - MDW

MELMDW

Melbourne

Fri 13/3

09:10-21:46

2 stops28h 36m

Chicago Midway

Fri 27/3

14:00-08:40

2 stops26h 40m

$2,222

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 25/12

14:15-11:06

2 stops37h 51m

Chicago Midway

Mon 12/1

13:49-08:30

2 stops25h 41m

$2,383

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 25/12

14:15-09:05

2 stops35h 50m

Chicago Midway

Wed 14/1

13:49-08:30

2 stops25h 41m

$2,383

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 25/12

14:15-11:06

2 stops37h 51m

Chicago Midway

Sun 11/1

13:49-08:30

2 stops25h 41m

$2,383

BrisbaneChicago

BNE - MDW

BNEMDW

Brisbane

Fri 16/1

10:40-17:37

2 stops22h 57m

Chicago Midway

Thu 29/1

19:16-08:20

2 stops45h 04m

$2,451

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 28/12

10:40-17:19

2 stops23h 39m

Chicago Midway

Sun 4/1

09:50-08:30

2 stops29h 40m

$2,459

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 27/12

10:40-17:19

2 stops23h 39m

Chicago Midway

Sun 11/1

13:28-06:50

2 stops24h 22m

$2,459

Flights are sorted by cheapest return flights first.

Deals found on 22/11

Showing 1-10 of 36 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 $2,154, Delta can have you in Chicago Midway Airport from Australia in 22h 49m. 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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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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