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Cheap flights from Sydney to Chicago Midway Airport from $1,497

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 14/12. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
19 Dec — 26 Dec1
1 adult
1 adult, Economy, 0 bags

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 19 November 2025.

Round-trip from

$2,085

One-way from

$1,497

Popular in

December

Cheapest in

March

Average price

$1,778
Delta
  • Delta
  • 12/1-25/1
  • 4 total stops
  • 50h 56m total
  • Sydney to Chicago
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14/12
  • 14/12
  • 2 total stops
  • 39h 50m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($627 potential increase over avg. return price).
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Cheapest flight prices on average. 4% potential price decrease ($96 potential savings vs. average return price).
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Average for round-trip flights in November 2025
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Find flight deals from Sydney to Midway

Enter your travel dates to find the best prices.

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 19 November 2025.

Thu 25/1214:15SYD - MDW
2 stops35h 34mDelta
Mon 12/113:49MDW - SYD
2 stops25h 41mDelta
Deal found 18/11$2,379
Mon 29/1210:40SYD - MDW
2 stops23h 39mDelta
Tue 13/109:32MDW - SYD
2 stops28h 18mDelta
Deal found 16/11$2,388
Sun 28/1210:40SYD - MDW
2 stops28h 42mDelta
Sun 11/109:32MDW - SYD
2 stops28h 18mDelta
Deal found 18/11$2,455
Tue 30/1214:15SYD - MDW
2 stops37h 51mDelta
Fri 9/119:16MDW - SYD
2 stops42h 34mDelta
Deal found 16/11$2,464
Fri 26/1210:40SYD - MDW
2 stops23h 39mDelta
Fri 9/119:16MDW - SYD
2 stops42h 34mDelta
Deal found 18/11$2,530
Sun 28/1210:40SYD - MDW
2 stops22h 40mDelta
Thu 8/111:21MDW - SYD
2 stops26h 29mDelta
Deal found 16/11$2,539
Wed 24/1210:40SYD - MDW
2 stops39h 09mDelta
Sun 11/113:28MDW - SYD
2 stops24h 22mDelta
Deal found 18/11$2,704
Tue 30/1210:40SYD - MDW
2 stops22h 40mDelta
Thu 8/111:21MDW - SYD
2 stops26h 29mDelta
Deal found 18/11$2,856
Wed 31/1210:40SYD - MDW
2 stops41h 26mDelta
Fri 9/119:16MDW - SYD
2 stops42h 34mDelta
Deal found 16/11$2,866
Wed 31/1210:40SYD - MDW
2 stops39h 09mDelta
Tue 13/113:28MDW - SYD
2 stops24h 22mDelta
Deal found 18/11$2,996
Tue 30/1210:40SYD - MDW
2 stops22h 40mDelta
Sat 10/113:28MDW - SYD
2 stops24h 22mDelta
Deal found 16/11$3,083
Sun 21/1210:40SYD - MDW
2 stops22h 40mDelta
Sun 4/109:50MDW - SYD
2 stops29h 40mDelta
Deal found 18/11$3,092

Cheapflights Fare Finder

 
Customise 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 647,157 searches. Data last updated 19 November 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 12/1

10:40-17:34

2 stops23h 54m

Chicago Midway

Sun 25/1

10:48-06:50

2 stops27h 02m

$2,085

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 2/2

14:15-22:22

2 stops25h 07m

Chicago Midway

Thu 19/2

13:49-08:30

2 stops25h 41m

$2,161

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 1/3

10:40-17:45

2 stops24h 05m

Chicago Midway

Sun 15/3

13:05-06:05

2 stops25h 00m

$2,313

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 25/12

14:15-08:49

2 stops35h 34m

Chicago Midway

Mon 12/1

13:49-08:30

2 stops25h 41m

$2,379

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 25/12

14:15-08:49

2 stops35h 34m

Chicago Midway

Wed 14/1

13:49-08:30

2 stops25h 41m

$2,379

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 25/12

14:15-08:49

2 stops35h 34m

Chicago Midway

Wed 7/1

13:28-08:30

2 stops26h 02m

$2,379

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 29/12

10:40-17:19

2 stops23h 39m

Chicago Midway

Tue 6/1

09:32-06:50

2 stops28h 18m

$2,379

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 25/12

14:15-08:49

2 stops35h 34m

Chicago Midway

Tue 6/1

13:28-06:50

2 stops24h 22m

$2,379

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 30/12

14:15-11:06

2 stops37h 51m

Chicago Midway

Tue 13/1

11:21-06:50

2 stops26h 29m

$2,379

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 29/12

10:40-17:19

2 stops23h 39m

Chicago Midway

Wed 14/1

13:28-08:30

2 stops26h 02m

$2,379

Flights are sorted by cheapest return flights first.

Deals found on 17/11

Showing 1-10 of 17 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 return 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?

    For a flight from Sydney to Chicago Midway, you will be flying from Kingsford Smith. Sydney Kingsford Smith (SYD) is just 7.5 km from the centre of the city. Kingsford Smith is the only Sydney airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Sydney Kingsford Smith on a regular basis.

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

    A quick flight from Sydney to Chicago Midway Airport can take about 23h 54m. Delta provides one of the quickest options available for as low as $2,085. There are 14861 km between Sydney and Chicago Midway Airport.

  • 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 holiday 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Sydney to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Sydney to O'Hare Intl flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Sydney to Midway?

When you search for this flight from Sydney to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Sydney to Midway?

Cheapflights helps you find that perfect flight to Midway from Sydney by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Sydney to Midway with no change fees?

Yes! Cheapflights helps users easily find flights from Sydney to Midway with no change fees.

Can Cheapflights notify me if prices for flights from Sydney to Midway become cheaper?

Of course! You can now track prices for flights from Sydney to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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