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$477+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$954
(Trip.com)

One-way from

$477
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$1,148
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 ($296 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($46 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This Trip.com deal was found by Cheapflights users on 9/15. 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 10/1310:10 amSYD - MDW
2 stops43h 28mMultiple Airlines
Mon 10/205:10 amMDW - SYD
2 stops34h 55mMultiple Airlines
Deal found 9/15$954
This Trip.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/3011:20 amSYD - MDW
2 stops41h 17mMultiple Airlines
Thu 11/66:25 amMDW - SYD
2 stops32h 00mMultiple Airlines
Deal found 9/15$966
This Delta deal was found by Cheapflights users on 9/15. 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 9/309:25 amSYD - MDW
2 stops24h 10mDelta
Wed 11/121:14 pmMDW - SYD
2 stops26h 16mDelta
Deal found 9/15$1,004
This Trip.com deal was found by Cheapflights users on 9/16. 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 10/3111:20 amSYD - MDW
2 stops41h 17mMultiple Airlines
Fri 11/76:30 amMDW - SYD
2 stops33h 30mMultiple Airlines
Deal found 9/16$1,014
This Trip.com deal was found by Cheapflights users on 9/16. 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.
Sat 11/111:20 amSYD - MDW
2 stops41h 10mMultiple Airlines
Sat 11/156:15 amMDW - SYD
2 stops33h 45mMultiple Airlines
Deal found 9/16$1,074
This Delta deal was found by Cheapflights users on 9/14. 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.
Wed 10/299:40 amSYD - MDW
2 stops28h 34mDelta
Wed 11/51:08 pmMDW - SYD
2 stops26h 22mDelta
Deal found 9/14$1,213
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 10/309:40 amSYD - MDW
2 stops22h 29mDelta
Thu 11/610:40 amMDW - SYD
2 stops28h 50mDelta
Deal found 9/14$1,341
This Delta deal was found by Cheapflights users on 9/15. 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 11/810:40 amSYD - MDW
2 stops24h 45mDelta
Sat 11/229:32 amMDW - SYD
2 stops29h 58mDelta
Deal found 9/15$1,478
This Delta deal was found by Cheapflights users on 9/14. 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.
Wed 10/810:25 amSYD - MDW
2 stops23h 18mDelta
Tue 10/149:35 amMDW - SYD
2 stops30h 00mDelta
Deal found 9/14$1,489
This Delta deal was found by Cheapflights users on 9/15. 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 9/189:25 amSYD - MDW
2 stops27h 11mDelta
Fri 10/179:35 amMDW - SYD
2 stops30h 00mDelta
Deal found 9/15$1,579

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 September 16, 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 10/13

10:10 am-1:38 pm

2 stops43h 28m

Chicago Midway

Mon 10/20

5:10 am-8:05 am

2 stops34h 55m

$954

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 9/30

9:25 am-5:35 pm

2 stops23h 10m

Chicago Midway

Wed 11/12

12:47 pm-8:30 am

2 stops26h 43m

$1,004

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 10/31

11:20 am-12:37 pm

2 stops41h 17m

Chicago Midway

Fri 11/7

6:30 am-9:00 am

2 stops33h 30m

$1,014

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 11/1

11:20 am-12:30 pm

2 stops41h 10m

Chicago Midway

Sat 11/15

6:15 am-9:00 am

2 stops33h 45m

$1,074

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 10/29

9:40 am-10:14 pm

2 stops28h 34m

Chicago Midway

Wed 11/5

1:08 pm-8:30 am

2 stops26h 22m

$1,213

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 10/30

9:40 am-4:09 pm

2 stops22h 29m

Chicago Midway

Thu 11/6

10:40 am-8:30 am

2 stops28h 50m

$1,341

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 11/8

10:40 am-6:25 pm

2 stops24h 45m

Chicago Midway

Sat 11/22

9:41 am-8:30 am

2 stops29h 49m

$1,480

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 10/8

10:25 am-5:43 pm

2 stops23h 18m

Chicago Midway

Tue 10/14

9:35 am-7:35 am

2 stops30h 00m

$1,489

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 12/12

2:05 pm-9:28 pm

1 stop24h 23m

Chicago Midway

Fri 1/23

6:00 am-7:25 am

2 stops32h 25m

$1,601

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 10/15

5:20 pm-4:05 pm

3 stops38h 45m

$477

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 16 results
1
2

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 10m. 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.

  • 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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