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Cheap flights from Sydney to Chicago Midway Airport from $763

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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
10 May — 17 May1
1 adult
1 adult, Economy, 0 bags

Cheap 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 10 April 2026.

Tue 19/509:15
SYD
-
MDW
2 stops23h 41m
Delta
Tue 26/513:22
MDW
-
SYD
2 stops26h 28m
Delta
Deal found 5/4$2,326
Tue 9/609:15
SYD
-
MDW
2 stops24h 16m
Delta
Tue 7/713:16
MDW
-
SYD
2 stops26h 34m
Delta
Deal found 6/4$2,360
Mon 25/509:15
SYD
-
MDW
2 stops23h 41m
Delta
Mon 1/609:23
MDW
-
SYD
2 stops30h 27m
Delta
Deal found 10/4$2,374
Mon 7/1210:40
SYD
-
MDW
2 stops24h 57m
Delta
Sun 10/113:00
MDW
-
SYD
2 stops26h 30m
Delta
Deal found 5/4$2,396
Wed 14/1010:15
SYD
-
MDW
2 stops22h 35m
Delta
Sat 24/1012:30
MDW
-
SYD
2 stops27h 00m
Delta
Deal found 5/4$2,418
Wed 9/1210:40
SYD
-
MDW
2 stops28h 05m
Delta
Sat 16/113:00
MDW
-
SYD
2 stops26h 30m
Delta
Deal found 8/4$2,431
Mon 4/509:15
SYD
-
MDW
2 stops28h 13m
Delta
Thu 21/509:22
MDW
-
SYD
2 stops30h 28m
Delta
Deal found 8/4$2,447
Sat 23/509:15
SYD
-
MDW
2 stops24h 18m
Delta
Sat 30/513:59
MDW
-
SYD
2 stops25h 51m
Delta
Deal found 7/4$2,468
Fri 10/709:15
SYD
-
MDW
2 stops24h 03m
Delta
Sun 26/713:49
MDW
-
SYD
2 stops26h 01m
Delta
Deal found 6/4$2,469

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 10 April 2026.

Round-trip from

$2,326

One-way from

$763

Popular in

April

Cheapest in

August

Average price

$2,257
Delta
  • Delta
  • 19/5-26/5
  • 4 total stops
  • 50h 09m total
  • Sydney to Chicago
Search Deals
3/9
  • 3/9
  • 3 total stops
  • 44h 47m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($188 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($72 potential savings vs. average return price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

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 10 April 2026.
Use the filters below to find and compare flights from Sydney to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight
Fastest return journey

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 28/5

09:15-17:56

2 stops23h 41m

Chicago Midway

Wed 10/6

13:49-06:50

2 stops26h 01m

$2,326

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 19/5

09:15-17:56

2 stops23h 41m

Chicago Midway

Tue 26/5

13:22-06:50

2 stops26h 28m

$2,326

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 9/6

09:15-18:31

2 stops24h 16m

Chicago Midway

Tue 7/7

13:16-06:50

2 stops26h 34m

$2,360

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 7/5

09:15-17:56

2 stops23h 41m

Chicago Midway

Wed 20/5

12:53-06:50

2 stops26h 57m

$2,374

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 25/5

09:15-17:56

2 stops23h 41m

Chicago Midway

Mon 1/6

09:23-06:50

2 stops30h 27m

$2,374

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 4/5

09:15-22:28

2 stops28h 13m

Chicago Midway

Thu 21/5

09:22-06:50

2 stops30h 28m

$2,447

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 23/5

09:15-17:56

2 stops23h 41m

Chicago Midway

Sat 30/5

13:22-06:50

2 stops26h 28m

$2,476

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 22/6

09:15-18:18

2 stops24h 03m

Chicago Midway

Sun 19/7

09:20-06:50

2 stops30h 30m

$2,541
Cheapest one-way

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 3/9

08:20-14:07

3 stops44h 47m

$763

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 24/6

19:20-15:15

3 stops58h 55m

$1,415

Flights are sorted by cheapest return flights first.

Deals found on 9/4

Showing 1-10 of 20 resultsSorted by cheapest first
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.

Cheapflights Insights

Everything you need to know about your flight from Sydney to Chicago Midway Airport

What’s the top stopover airport for flights from Sydney to Chicago Midway Airport?

Share of one-stop return flights from Sydney to Chicago Midway Airport chosen by Cheapflights users in the past 12 months, using the same stopover each way.

San Francisco (SFO) – chosen by Cheapflights users on 67% of one-stop itineraries from Sydney to Chicago Midway Airport on Cheapflights.

What’s the cheapest stopover airport for flights from Sydney to Chicago Midway Airport?

Average return fare for one-stop flights from Sydney to Chicago Midway Airport, chosen by Cheapflights users in the past 12 months, with the same stopover each way.

Hong Kong (HKG) is the most affordable one-stop option, with an average return flight price of $2,091.

What’s the fastest stopover option from Sydney to Chicago Midway Airport?

Shortest average travel time for one-stop one-way flights from Sydney to Chicago Midway Airport, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by stopover airport.

Flights via San Francisco (SFO) have the shortest average one-way travel time for one-stop routes: 19h 35m.

Which airport typically offers the quickest stopover for flights from Sydney to Chicago Midway Airport?

Average stopover duration for one-stop one-way flights from Sydney to Chicago Midway Airport, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via San Francisco (SFO) offer the fastest connection on this route, with an average stopover time of 1h 35m.

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 41m. Delta provides one of the quickest options available for as low as $2,326. 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

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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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