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$542+ Cheap flights from Midway (MDW) to Sydney (SYD)

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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SYD
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Midway to Sydney

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Sydney (SYD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 15, 2025.

Round-trip from

$1,033
(Trip.com)

One-way from

$542
(Trip.com)

Popular in

December

Cheapest in

August

Average price

$999
From Chicago Midway to Sydney Kingsford Smith
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One-way flight from Chicago Midway to Sydney Kingsford Smith
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Highest demand for flights based on searches. 15% potential increase in price ($184 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($37 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Sydney

Cheapest flights from Midway to Sydney
Explore the most affordable flight options available from Midway to Sydney. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Trip.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2712:03 pmMDW - SYD
2 stops28h 57mMultiple Airlines
Sun 11/92:05 pmSYD - MDW
2 stops24h 58mMultiple Airlines
Deal found 9/15$1,033
This Trip.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/209:44 amMDW - SYD
2 stops30h 21mMultiple Airlines
Sun 11/22:05 pmSYD - MDW
2 stops24h 58mMultiple Airlines
Deal found 9/15$1,072
This Trip.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:30 amMDW - SYD
2 stops34h 30mMultiple Airlines
Thu 11/611:20 amSYD - MDW
2 stops41h 10mMultiple Airlines
Deal found 9/15$1,411
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/205:30 amMDW - SYD
2 stops38h 30mMultiple Airlines
Fri 12/122:05 pmSYD - MDW
1 stop24h 23mMultiple Airlines
Deal found 9/13$1,439
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/161:47 pmMDW - SYD
2 stops25h 43mDelta
Tue 12/910:40 amSYD - MDW
2 stops29h 52mDelta
Deal found 9/13$1,467
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/227:02 pmMDW - SYD
2 stops44h 28mDelta
Mon 12/810:40 amSYD - MDW
2 stops29h 52mDelta
Deal found 9/13$1,485
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:48 amMDW - SYD
2 stops27h 42mDelta
Fri 1/3010:40 amSYD - MDW
2 stops28h 06mDelta
Deal found 9/15$1,517
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/61:08 pmMDW - SYD
2 stops26h 22mDelta
Sat 11/2210:40 amSYD - MDW
2 stops29h 52mDelta
Deal found 9/15$1,567
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1611:21 amMDW - SYD
2 stops27h 04mMultiple Airlines
Fri 12/122:05 pmSYD - MDW
1 stop24h 23mMultiple Airlines
Deal found 9/13$1,571
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/211:48 pmMDW - SYD
2 stops25h 47mDelta
Tue 12/210:40 amSYD - MDW
2 stops24h 38mDelta
Deal found 9/15$1,617
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/13:00 pmMDW - SYD
2 stops24h 30mDelta
Sun 11/1610:40 amSYD - MDW
2 stops22h 58mDelta
Deal found 9/13$1,667
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2510:08 amMDW - SYD
2 stops29h 22mDelta
Tue 1/62:15 pmSYD - MDW
2 stops24h 31mDelta
Deal found 9/13$1,712

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Sydney 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 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Sydney that are best for you.

Fly from

Midway

Fly to

Sydney

Route

Depart

Return

Price

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 10/30

6:30 am-9:00 am

2 stops34h 30m

Sydney Kingsford Smith

Thu 11/6

11:20 am-11:30 am

2 stops41h 10m

$1,411

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 12/9

9:34 am-8:30 am

2 stops29h 56m

Sydney Kingsford Smith

Tue 12/23

10:40 am-5:19 pm

2 stops23h 39m

$1,467

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 11/10

1:47 pm-8:30 am

2 stops25h 43m

Sydney Kingsford Smith

Wed 11/26

10:40 am-6:08 pm

2 stops24h 28m

$1,467

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 11/18

1:47 pm-8:30 am

2 stops25h 43m

Sydney Kingsford Smith

Mon 12/8

10:40 am-11:32 pm

2 stops29h 52m

$1,467

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 11/10

12:47 pm-8:30 am

2 stops26h 43m

Sydney Kingsford Smith

Sun 11/23

10:40 am-4:38 pm

2 stops22h 58m

$1,467

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 11/24

1:47 pm-8:30 am

2 stops25h 43m

Sydney Kingsford Smith

Sun 12/7

10:40 am-11:32 pm

2 stops29h 52m

$1,467

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 11/19

10:47 am-8:30 am

2 stops28h 43m

Sydney Kingsford Smith

Mon 12/8

10:40 am-4:36 pm

2 stops22h 56m

$1,467

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 11/16

1:47 pm-8:30 am

2 stops25h 43m

Sydney Kingsford Smith

Tue 12/9

10:40 am-11:32 pm

2 stops29h 52m

$1,467

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 11/19

1:14 pm-8:30 am

2 stops26h 16m

Sydney Kingsford Smith

Tue 12/9

10:40 am-11:32 pm

2 stops29h 52m

$1,467

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 11/18

12:47 pm-8:30 am

2 stops26h 43m

Sydney Kingsford Smith

Tue 12/9

10:40 am-11:32 pm

2 stops29h 52m

$1,467

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 20 results
1
2

Best time to book a flight from Midway to Sydney

Have a flexible travel schedule? Discover the best time to fly to Sydney from Midway with our price prediction graph.
Estimated round-trip 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.

Related info for your journey

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

  • What airport do you fly into for flights to Sydney from Chicago Midway?

    For a flight from Chicago Midway to Sydney, you will be flying into Kingsford Smith. Sydney Kingsford Smith (SYD) is just 4.6 mi from the center of the city. Kingsford Smith is the only Sydney airport and it handles 0 inbound flights from Chicago Midway per day. 0 airlines have flights to Sydney Kingsford Smith from Chicago Midway on a regular basis.

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

    Departing from Chicago Midway Airport to Sydney will take you 29h 56m. The distance between Chicago Midway Airport and Sydney is about 9234 mi.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from Chicago Midway Airport to Sydney?

    Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Sydney (average of $1,032). Flying from Chicago Midway Airport to Sydney in December is currently the most expensive (average of $1,627). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Sydney?

Book flights to Sydney if you plan to visit one of these locations
Parramatta
Wollongong
Manly
Coogee

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