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$885+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap 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 December 28, 2025.

This Delta deal was found by Cheapflights users on 12/28. 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 12/3010:40 amSYD - MDW
2 stops22h 40mDelta
Thu 3/510:49 amMDW - SYD
2 stops27h 01mDelta
Deal found 12/28$1,744

Find 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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$1,312
(Trip.com)

One-way from

$885
(Delta)

Popular in

December

Cheapest in

March

Average price

$1,371
Provider with most accurate pricing for Sydney Kingsford Smith-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Sydney Kingsford Smith-Chicago Midway flights.
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From Sydney Kingsford Smith to Chicago Midway
Search Deals
One-way flight from Sydney Kingsford Smith to Chicago Midway
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($235 potential increase over avg. RT price).
Search Deals
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 December 2025
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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 December 28, 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 2/9

11:20 am-10:19 pm

2 stops27h 59m

Chicago Midway

Mon 2/16

6:00 am-9:00 am

2 stops34h 00m

$1,312

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 6/3

9:15 am-6:31 pm

2 stops24h 16m

Chicago Midway

Mon 8/10

2:00 pm-6:35 am

2 stops25h 35m

$1,389

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 6/2

9:15 am-9:45 pm

2 stops27h 30m

Chicago Midway

Mon 8/10

2:00 pm-6:35 am

2 stops25h 35m

$1,389

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 5/28

9:15 am-9:45 pm

2 stops27h 30m

Chicago Midway

Mon 8/10

2:00 pm-6:35 am

2 stops25h 35m

$1,389

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 6/1

9:15 am-6:05 pm

2 stops23h 50m

Chicago Midway

Mon 8/10

2:00 pm-6:35 am

2 stops25h 35m

$1,389

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 4/20

9:15 am-6:45 pm

2 stops24h 30m

Chicago Midway

Wed 5/6

2:12 pm-6:35 am

2 stops25h 23m

$1,390

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 5/31

9:15 am-6:05 pm

2 stops23h 50m

Chicago Midway

Mon 8/10

1:05 pm-6:35 am

2 stops26h 30m

$1,439

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 6/12

9:15 am-6:31 pm

2 stops24h 16m

Chicago Midway

Sun 7/12

2:00 pm-6:35 am

2 stops25h 35m

$1,440

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 4/21

9:15 am-5:54 pm

2 stops23h 39m

Chicago Midway

Thu 5/7

1:05 pm-6:35 am

2 stops26h 30m

$1,440

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 1/16

10:40 am-10:07 pm

2 stops28h 27m

Chicago Midway

Fri 1/30

1:26 pm-8:30 am

2 stops26h 04m

$1,454

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 16 results
1
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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 December.
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 24h 16m. 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
Merrillville
Hammond
Porter
Benton Harbor

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