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Midway

$721+ Cheap flights from Sydney (SYD) to Midway (MDW)

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 11/22. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Cheap flight deals from Sydney to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Sydney (SYD) to Midway (MDW). 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 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$1,403
(Delta)

One-way from

$721
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$1,155
Provider with most accurate pricing for Sydney Kingsford Smith-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Sydney Kingsford Smith-Chicago Midway flights.
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From Sydney Kingsford Smith to Chicago Midway
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One-way flight from Sydney Kingsford Smith to Chicago Midway
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Highest demand for flights based on searches. 19% potential increase in price ($242 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($40 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Sydney to Midway

Cheapest flights from Sydney to Midway
Explore the most affordable flight options available from Sydney to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This Delta deal was found by Cheapflights users on 11/13. 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 12/2810:40 amSYD - MDW
2 stops22h 40mDelta
Sun 1/49:50 amMDW - SYD
2 stops28h 00mDelta
Deal found 11/13$1,600
This Delta deal was found by Cheapflights users on 11/12. 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 11/1310:40 amSYD - MDW
2 stops24h 38mDelta
Wed 11/261:15 pmMDW - SYD
2 stops26h 15mDelta
Deal found 11/12$1,647
This Delta deal was found by Cheapflights users on 11/11. 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 12/2610:40 amSYD - MDW
2 stops23h 39mDelta
Fri 1/26:00 amMDW - SYD
2 stops33h 30mDelta
Deal found 11/11$1,648
This Delta deal was found by Cheapflights users on 11/13. 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.
Mon 11/1710:40 amSYD - MDW
2 stops24h 38mDelta
Sun 11/309:34 amMDW - SYD
2 stops29h 56mDelta
Deal found 11/13$1,649
This Delta deal was found by Cheapflights users on 11/12. 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 11/1410:40 amSYD - MDW
2 stops24h 38mDelta
Thu 11/2710:47 amMDW - SYD
2 stops28h 43mDelta
Deal found 11/12$1,745
This Delta deal was found by Cheapflights users on 11/11. 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 11/1610:40 amSYD - MDW
2 stops22h 58mDelta
Thu 11/201:15 pmMDW - SYD
2 stops26h 15mDelta
Deal found 11/11$1,746
This Delta deal was found by Cheapflights users on 11/13. 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.
Fri 11/1410:40 amSYD - MDW
2 stops24h 28mDelta
Fri 11/2112:47 pmMDW - SYD
2 stops26h 43mDelta
Deal found 11/13$1,747
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 11/138:30 amSYD - MDW
2 stops29h 14mMultiple Airlines
Wed 11/265:30 amMDW - SYD
1 stop32h 25mMultiple Airlines
Deal found 11/12$1,880
This Delta deal was found by Cheapflights users on 11/12. 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 12/302:15 pmSYD - MDW
2 stops25h 07mDelta
Sat 1/109:34 amMDW - SYD
2 stops28h 16mDelta
Deal found 11/12$2,002
This Delta deal was found by Cheapflights users on 11/12. 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 12/1210:40 amSYD - MDW
2 stops24h 38mDelta
Sat 1/109:34 amMDW - SYD
2 stops28h 16mDelta
Deal found 11/12$2,063
This Delta deal was found by Cheapflights users on 11/11. 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 12/1510:40 amSYD - MDW
2 stops30h 07mDelta
Thu 1/151:28 pmMDW - SYD
2 stops26h 02mDelta
Deal found 11/11$2,112
This Delta deal was found by Cheapflights users on 11/12. 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 12/1410:40 amSYD - MDW
2 stops30h 07mDelta
Fri 1/29:50 amMDW - SYD
2 stops29h 40mDelta
Deal found 11/12$2,274

Cheapflights Fare Finder

 
Customize your flight search to find flights from Sydney 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 2,558,603 searches. Data last updated November 13, 2025.
Use the filters below to find and compare flights from Sydney to Chicago Midway Airport that are best for you.

Fly from

Sydney

Fly to

Midway

Route

Depart

Return

Price

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 2/2

10:40 am-5:32 pm

2 stops23h 52m

Chicago Midway

Thu 2/19

12:46 pm-8:30 am

2 stops26h 44m

$1,403

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 2/19

2:15 pm-10:44 pm

2 stops25h 29m

Chicago Midway

Mon 3/2

9:34 am-8:30 am

2 stops29h 56m

$1,501

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 12/28

10:40 am-4:20 pm

2 stops22h 40m

Chicago Midway

Sun 1/4

9:50 am-6:50 am

2 stops28h 00m

$1,600

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 12/10

10:40 am-11:47 pm

2 stops30h 07m

Chicago Midway

Mon 12/15

9:34 am-8:30 am

2 stops29h 56m

$1,647

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 2/2

10:40 am-5:55 pm

2 stops24h 15m

Chicago Midway

Sun 2/8

1:28 pm-8:30 am

2 stops26h 02m

$1,647

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 12/26

10:40 am-4:20 pm

2 stops22h 40m

Chicago Midway

Fri 1/2

9:50 am-8:30 am

2 stops29h 40m

$1,648

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 12/30

2:15 pm-10:22 pm

2 stops25h 07m

Chicago Midway

Sat 1/10

9:34 am-6:50 am

2 stops28h 16m

$2,002

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 12/12

10:40 am-6:18 pm

2 stops24h 38m

Chicago Midway

Sat 1/10

9:34 am-6:50 am

2 stops28h 16m

$2,063

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 12/15

10:40 am-11:47 pm

2 stops30h 07m

Chicago Midway

Thu 1/15

1:28 pm-8:30 am

2 stops26h 02m

$2,112

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 12/14

10:40 am-11:47 pm

2 stops30h 07m

Chicago Midway

Fri 1/2

9:50 am-8:30 am

2 stops29h 40m

$2,274

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 19 results
1
2

Compare providers for flights from Sydney to Midway

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 Sydney to Midway in November.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 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 Sydney-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Sydney-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Sydney-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Sydney-Chicago Midway Airport 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 Sydney-Chicago Midway Airport 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 Sydney to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Sydney 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 Sydney to Midway. 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 from for flights from Sydney to Chicago Midway?

    Sydney Kingsford Smith (SYD) is the airport you will fly out of if you book a flight from Sydney to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Kingsford Smith; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Sydney airport to Chicago Midway. It is only a 4.6 mi journey to Kingsford Smith (SYD) from Sydney’s city center.

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

    Departing from Sydney to Chicago Midway Airport will take you 23h 52m. The distance between Sydney and Chicago Midway Airport is about 9234 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Sydney 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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