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$778+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SYD
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
1 adult, Economy
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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 November 5, 2025.

This Trip.com deal was found by Cheapflights users on 11/4. 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 12/16:05 amMDW - SYD
2 stops33h 55mMultiple Airlines
Sun 12/145:45 pmSYD - MDW
2 stops34h 23mMultiple Airlines
Deal found 11/4$1,248
This Delta deal was found by Cheapflights users on 11/5. 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.
Mon 12/11:15 pmMDW - SYD
2 stops26h 15mDelta
Mon 12/810:40 amSYD - MDW
2 stops22h 54mDelta
Deal found 11/5$1,268
This Delta deal was found by Cheapflights users on 11/3. 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 11/2512:47 pmMDW - SYD
2 stops26h 43mDelta
Sun 12/710:40 amSYD - MDW
2 stops30h 07mDelta
Deal found 11/3$1,269
This Delta deal was found by Cheapflights users on 11/4. 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 11/151:47 pmMDW - SYD
2 stops25h 43mDelta
Mon 11/2410:40 amSYD - MDW
2 stops24h 28mDelta
Deal found 11/4$1,318
This Delta deal was found by Cheapflights users on 11/3. 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 11/251:47 pmMDW - SYD
2 stops25h 43mDelta
Thu 12/1110:40 amSYD - MDW
2 stops22h 38mDelta
Deal found 11/3$1,319
This Delta deal was found by Cheapflights users on 11/4. 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 11/279:34 amMDW - SYD
2 stops29h 56mDelta
Thu 12/1110:40 amSYD - MDW
2 stops22h 38mDelta
Deal found 11/4$1,354
This Delta deal was found by Cheapflights users on 11/4. 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 11/610:40 amMDW - SYD
2 stops28h 50mDelta
Sat 11/2210:40 amSYD - MDW
2 stops24h 38mDelta
Deal found 11/4$1,368
This Delta deal was found by Cheapflights users on 11/2. 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 12/412:50 pmMDW - SYD
2 stops26h 40mDelta
Sun 12/1410:40 amSYD - MDW
2 stops30h 07mDelta
Deal found 11/2$1,439
This Delta deal was found by Cheapflights users on 11/3. 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.
Mon 12/296:00 amMDW - SYD
2 stops33h 30mDelta
Wed 1/2810:40 amSYD - MDW
2 stops23h 52mDelta
Deal found 11/3$1,688
This Delta deal was found by Cheapflights users on 11/5. 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 12/61:50 pmMDW - SYD
2 stops25h 40mDelta
Sat 12/2010:40 amSYD - MDW
2 stops23h 39mDelta
Deal found 11/5$1,716
This Delta deal was found by Cheapflights users on 11/3. 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 11/229:32 amMDW - SYD
2 stops29h 58mDelta
Tue 12/302:15 pmSYD - MDW
2 stops25h 07mDelta
Deal found 11/3$1,738

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 November 5, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$1,145
(Trip.com)

One-way from

$778
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$995
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. 17% potential increase in price ($207 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($37 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 5, 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

Mon 12/1

6:05 am-9:00 am

2 stops33h 55m

Sydney Kingsford Smith

Sun 12/14

5:45 pm-11:08 am

2 stops34h 23m

$1,248

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 12/1

1:15 pm-8:30 am

2 stops26h 15m

Sydney Kingsford Smith

Mon 12/8

10:40 am-4:34 pm

2 stops22h 54m

$1,268

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 1/27

1:28 pm-8:30 am

2 stops26h 02m

Sydney Kingsford Smith

Mon 2/2

10:40 am-5:32 pm

2 stops23h 52m

$1,268

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 12/3

10:49 am-8:30 am

2 stops28h 41m

Sydney Kingsford Smith

Wed 12/10

10:40 am-4:34 pm

2 stops22h 54m

$1,269

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 12/2

1:50 pm-8:30 am

2 stops25h 40m

Sydney Kingsford Smith

Tue 12/9

10:40 am-11:47 pm

2 stops30h 07m

$1,269

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 11/25

10:47 am-8:30 am

2 stops28h 43m

Sydney Kingsford Smith

Tue 12/9

10:40 am-4:34 pm

2 stops22h 54m

$1,269

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 11/25

12:47 pm-8:30 am

2 stops26h 43m

Sydney Kingsford Smith

Wed 12/10

10:40 am-11:47 pm

2 stops30h 07m

$1,269

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 11/15

1:47 pm-8:30 am

2 stops25h 43m

Sydney Kingsford Smith

Mon 11/24

10:40 am-6:08 pm

2 stops24h 28m

$1,318

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 2/2

1:49 pm-8:30 am

2 stops25h 41m

Sydney Kingsford Smith

Sat 2/21

2:15 pm-10:44 pm

2 stops25h 29m

$1,319

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 11/25

10:47 am-8:30 am

2 stops28h 43m

Sydney Kingsford Smith

Sat 12/6

10:40 am-11:47 pm

2 stops30h 07m

$1,319

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Sydney flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 15m. 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
Coogee

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