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$514+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$1,400
(Delta)

One-way from

$514
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$1,039
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. 22% potential increase in price ($300 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($50 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/13. 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 12/2610:40 amSYD - MDW
2 stops23h 57mDelta
Fri 1/29:30 amMDW - SYD
2 stops30h 00mDelta
Deal found 8/13$1,449
This Delta deal was found by Cheapflights users on 8/14. 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 12/272:15 pmSYD - MDW
2 stops24h 50mDelta
Thu 1/159:30 amMDW - SYD
2 stops28h 20mDelta
Deal found 8/14$1,455
This Delta deal was found by Cheapflights users on 8/13. 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 8/259:25 amSYD - MDW
2 stops23h 12mDelta
Tue 9/99:30 amMDW - SYD
2 stops30h 05mDelta
Deal found 8/13$1,644
This Delta deal was found by Cheapflights users on 8/12. 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.
Wed 8/279:25 amSYD - MDW
2 stops23h 12mDelta
Wed 9/310:31 amMDW - SYD
2 stops29h 04mDelta
Deal found 8/12$1,645
This Delta deal was found by Cheapflights users on 8/13. 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 8/249:25 amSYD - MDW
2 stops23h 22mDelta
Tue 9/91:08 pmMDW - SYD
2 stops26h 27mDelta
Deal found 8/13$1,693
This Delta deal was found by Cheapflights users on 8/14. 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 8/299:25 amSYD - MDW
2 stops23h 12mDelta
Mon 9/11:08 pmMDW - SYD
2 stops26h 27mDelta
Deal found 8/14$1,694
This Delta deal was found by Cheapflights users on 8/13. 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.
Wed 8/279:25 amSYD - MDW
2 stops23h 12mDelta
Sat 8/3012:15 pmMDW - SYD
2 stops27h 20mDelta
Deal found 8/13$1,700
This Delta deal was found by Cheapflights users on 8/14. 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 12/272:15 pmSYD - MDW
2 stops24h 50mDelta
Wed 1/149:30 amMDW - SYD
2 stops30h 00mDelta
Deal found 8/14$1,716
This Delta deal was found by Cheapflights users on 8/13. 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 9/59:25 amSYD - MDW
2 stops23h 12mDelta
Thu 9/181:43 pmMDW - SYD
2 stops25h 52mDelta
Deal found 8/13$1,742
This Delta deal was found by Cheapflights users on 8/14. 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 stops28h 04mDelta
Thu 1/159:30 amMDW - SYD
2 stops30h 00mDelta
Deal found 8/14$1,913
This Delta deal was found by Cheapflights users on 8/14. 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 9/159:25 amSYD - MDW
2 stops23h 10mDelta
Wed 10/151:08 pmMDW - SYD
2 stops26h 27mDelta
Deal found 8/14$1,938

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 August 14, 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 1/12

10:40 am-6:08 pm

2 stops24h 28m

Chicago Midway

Thu 1/29

1:00 pm-6:50 am

2 stops24h 50m

$1,400

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 12/26

10:40 am-5:37 pm

2 stops23h 57m

Chicago Midway

Fri 1/2

9:30 am-8:30 am

2 stops30h 00m

$1,449

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 12/27

2:15 pm-10:05 pm

2 stops24h 50m

Chicago Midway

Thu 1/15

9:30 am-6:50 am

2 stops28h 20m

$1,455

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 10/15

10:25 am-6:25 pm

2 stops24h 00m

Chicago Midway

Tue 10/21

10:35 am-7:35 am

2 stops29h 00m

$1,644

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 10/23

10:25 am-1:08 pm

2 stops42h 43m

Chicago Midway

Mon 10/27

1:48 pm-7:30 am

2 stops25h 42m

$1,644

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 8/25

9:25 am-5:37 pm

2 stops23h 12m

Chicago Midway

Tue 9/9

9:30 am-6:35 am

2 stops30h 05m

$1,644

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 8/27

9:25 am-5:37 pm

2 stops23h 12m

Chicago Midway

Wed 9/3

10:31 am-6:35 am

2 stops29h 04m

$1,645

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 9/7

9:25 am-9:26 pm

2 stops27h 01m

Chicago Midway

Mon 9/15

1:08 pm-6:35 am

2 stops26h 27m

$1,693

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 8/24

9:25 am-5:47 pm

2 stops23h 22m

Chicago Midway

Tue 9/9

1:08 pm-6:35 am

2 stops26h 27m

$1,693

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 8/29

9:25 am-5:37 pm

2 stops23h 12m

Chicago Midway

Mon 9/1

1:08 pm-6:35 am

2 stops26h 27m

$1,694

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 18 results
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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.

  • 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.

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

    Currently, April is the cheapest month in which you can book a flight from Sydney to Chicago Midway Airport (average of $160). Flying from Sydney to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Chicago Midway Airport?

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

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