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$682+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SYD
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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Cheap 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 January 20, 2026.

This Trip.com deal was found by Cheapflights users on 1/18. 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.
Wed 2/116:15 am
MDW
-
SYD
2 stops33h 45m
Multiple Airlines
Mon 2/2311:20 am
SYD
-
MDW
2 stops29h 24m
Multiple Airlines
Deal found 1/18$1,423
This Delta deal was found by Cheapflights users on 1/20. 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 2/811:45 am
MDW
-
SYD
2 stops26h 05m
Delta
Tue 3/101:15 pm
SYD
-
MDW
2 stops25h 16m
Delta
Deal found 1/20$1,469
This Delta deal was found by Cheapflights users on 1/20. 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 2/101:26 pm
MDW
-
SYD
2 stops26h 04m
Delta
Tue 3/179:40 am
SYD
-
MDW
2 stops25h 00m
Delta
Deal found 1/20$1,470
This Delta deal was found by Cheapflights users on 1/20. 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 3/121:10 pm
MDW
-
SYD
2 stops24h 55m
Delta
Wed 3/259:40 am
SYD
-
MDW
2 stops25h 00m
Delta
Deal found 1/20$1,519
This Delta deal was found by Cheapflights users on 1/19. 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 2/119:53 am
MDW
-
SYD
2 stops29h 37m
Delta
Fri 2/2710:40 am
SYD
-
MDW
2 stops24h 05m
Delta
Deal found 1/19$1,520
This Delta deal was found by Cheapflights users on 1/19. 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 6/141:00 pm
MDW
-
SYD
2 stops26h 35m
Delta
Sun 7/129:15 am
SYD
-
MDW
2 stops23h 50m
Delta
Deal found 1/19$1,541
This Delta deal was found by Cheapflights users on 1/19. 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.
Fri 4/171:10 pm
MDW
-
SYD
2 stops26h 25m
Delta
Sat 4/259:15 am
SYD
-
MDW
2 stops24h 30m
Delta
Deal found 1/19$1,570
This Trip.com deal was found by Cheapflights users on 1/19. 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.
Fri 2/67:30 am
MDW
-
SYD
2 stops32h 30m
Multiple Airlines
Sat 2/1411:20 am
SYD
-
MDW
2 stops51h 09m
Multiple Airlines
Deal found 1/19$1,619
This Delta deal was found by Cheapflights users on 1/18. 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 3/112:45 pm
MDW
-
SYD
2 stops25h 05m
Delta
Tue 3/3110:15 am
SYD
-
MDW
2 stops24h 25m
Delta
Deal found 1/18$1,620
This Trip.com deal was found by Cheapflights users on 1/18. 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.
Fri 2/69:45 am
MDW
-
SYD
2 stops30h 15m
Multiple Airlines
Sat 2/2111:20 am
SYD
-
MDW
2 stops51h 09m
Multiple Airlines
Deal found 1/18$1,630
This Kiwi.com deal was found by Cheapflights users on 1/17. 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.
Mon 2/99:45 am
MDW
-
SYD
1 stop28h 10m
Multiple Airlines
Thu 2/266:00 am
SYD
-
MDW
2 stops32h 12m
Multiple Airlines
Deal found 1/17$1,641

Find 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 January 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$1,423
(Trip.com)

One-way from

$682
(Kiwi.com)

Popular in

December

Cheapest in

June

Average price

$1,364
Provider with most accurate pricing for Chicago Midway-Sydney Kingsford Smith flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Sydney Kingsford Smith flights.
Search Deals
From Chicago Midway to Sydney Kingsford Smith
Search Deals
One-way flight from Chicago Midway to Sydney Kingsford Smith
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($231 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($47 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 20, 2026.
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

Sun 2/8

11:45 am-6:50 am

2 stops26h 05m

Sydney Kingsford Smith

Tue 3/10

1:15 pm-10:31 pm

2 stops25h 16m

$1,469

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 2/10

12:46 pm-8:30 am

2 stops26h 44m

Sydney Kingsford Smith

Tue 3/3

10:40 am-5:45 pm

2 stops24h 05m

$1,469

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 1/26

1:26 pm-8:30 am

2 stops26h 04m

Sydney Kingsford Smith

Tue 2/10

10:40 am-5:55 pm

2 stops24h 15m

$1,470

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 2/10

12:46 pm-6:50 am

2 stops25h 04m

Sydney Kingsford Smith

Tue 3/17

9:40 am-5:54 pm

2 stops24h 14m

$1,470

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 2/1

12:46 pm-8:30 am

2 stops26h 44m

Sydney Kingsford Smith

Sun 2/15

10:40 am-10:31 pm

2 stops28h 51m

$1,470

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 3/1

1:28 pm-8:30 am

2 stops26h 02m

Sydney Kingsford Smith

Sun 3/8

10:40 am-5:40 pm

2 stops24h 00m

$1,470

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 2/9

10:46 am-8:30 am

2 stops28h 44m

Sydney Kingsford Smith

Mon 2/23

2:15 pm-9:54 am

2 stops36h 39m

$1,470

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 2/10

1:26 pm-8:30 am

2 stops26h 04m

Sydney Kingsford Smith

Mon 2/23

2:15 pm-9:54 am

2 stops36h 39m

$1,470

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 3/4

1:29 pm-8:30 am

2 stops26h 01m

Sydney Kingsford Smith

Wed 3/11

9:40 am-10:31 pm

2 stops28h 51m

$1,470

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 2/12

3:00 pm-12:35 pm

2 stops28h 35m

$682

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

Showing 1-10 of 18 results
1
2

Compare providers for flights from Midway to Sydney

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Sydney in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Sydney flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Sydney flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Sydney flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Sydney flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Sydney flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 26h 05m. 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.

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

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Alternative routes for Midway to Sydney

See prices for flight routes from nearby airports that may be better suited for you.
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