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Cheap flights from Sydney to Chicago Midway Airport from $1,282

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 23/7. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
7 Jun — 14 Jun1
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 8 May 2026.

Tue 25/809:15
SYD
-
MDW
2 stops24h 18m
Delta
Thu 1/1013:00
MDW
-
SYD
2 stops26h 50m
Delta
Deal found 7/5$2,018
Thu 4/609:15
SYD
-
MDW
2 stops23h 41m
Delta
Wed 12/813:52
MDW
-
SYD
2 stops25h 58m
Delta
Deal found 6/5$2,349
Tue 2/609:15
SYD
-
MDW
2 stops24h 18m
Delta
Wed 10/613:49
MDW
-
SYD
2 stops26h 01m
Delta
Deal found 6/5$2,351
Thu 7/509:15
SYD
-
MDW
2 stops23h 41m
Delta
Wed 20/512:53
MDW
-
SYD
2 stops26h 57m
Delta
Deal found 5/5$2,355
Thu 11/609:15
SYD
-
MDW
2 stops24h 16m
Delta
Wed 22/713:49
MDW
-
SYD
2 stops26h 01m
Delta
Deal found 4/5$2,362
Thu 11/609:15
SYD
-
MDW
2 stops28h 02m
Delta
Tue 21/712:41
MDW
-
SYD
2 stops27h 09m
Delta
Deal found 4/5$2,364
Mon 11/509:15
SYD
-
MDW
2 stops24h 18m
Delta
Mon 18/513:22
MDW
-
SYD
2 stops26h 28m
Delta
Deal found 7/5$2,371
Mon 27/709:15
SYD
-
MDW
2 stops24h 03m
Delta
Wed 19/812:46
MDW
-
SYD
2 stops27h 04m
Delta
Deal found 7/5$2,407
Tue 25/809:15
SYD
-
MDW
2 stops24h 18m
Delta
Wed 30/913:05
MDW
-
SYD
2 stops26h 45m
Delta
Deal found 5/5$2,421
Fri 7/809:15
SYD
-
MDW
2 stops24h 18m
Delta
Sun 16/813:27
MDW
-
SYD
2 stops26h 23m
Delta
Deal found 7/5$2,429
Fri 12/609:15
SYD
-
MDW
2 stops24h 16m
Delta
Tue 21/711:05
MDW
-
SYD
2 stops28h 45m
Delta
Deal found 4/5$2,432
Thu 4/609:15
SYD
-
MDW
2 stops24h 18m
Delta
Thu 11/612:50
MDW
-
SYD
2 stops27h 00m
Delta
Deal found 7/5$2,442

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 8 May 2026.

Round-trip from

$2,018

One-way from

$1,282

Popular in

April

Cheapest in

August

Average price

$1,686
Delta
  • Delta
  • 25/8-1/10
  • 4 total stops
  • 51h 08m total
  • Sydney to Chicago
Search Deals
23/7
  • 23/7
  • 2 total stops
  • 25h 08m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($200 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($67 potential savings vs. average return price).
Search Deals
Average for round-trip flights in May 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 8 May 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 4/6

09:15-17:56

2 stops23h 41m

Chicago Midway

Wed 12/8

13:52-06:50

2 stops25h 58m

$2,349

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 11/6

09:15-18:18

2 stops24h 03m

Chicago Midway

Wed 22/7

13:49-06:50

2 stops26h 01m

$2,362

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 11/6

09:15-18:18

2 stops24h 03m

Chicago Midway

Mon 20/7

13:49-06:50

2 stops26h 01m

$2,362

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 27/7

09:15-18:18

2 stops24h 03m

Chicago Midway

Wed 19/8

12:46-06:50

2 stops27h 04m

$2,407

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 7/8

09:15-18:33

2 stops24h 18m

Chicago Midway

Sun 16/8

13:27-06:50

2 stops26h 23m

$2,429

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 13/6

09:15-18:11

2 stops23h 56m

Chicago Midway

Wed 22/7

13:18-06:50

2 stops26h 32m

$2,432

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 12/6

09:15-18:31

2 stops24h 16m

Chicago Midway

Tue 21/7

11:05-06:50

2 stops28h 45m

$2,432

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 4/6

09:15-18:33

2 stops24h 18m

Chicago Midway

Thu 11/6

12:50-06:50

2 stops27h 00m

$2,442

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 9/10

10:15-16:50

2 stops22h 35m

Chicago Midway

Tue 13/10

12:30-07:50

2 stops27h 20m

$2,464
Cheapest one-way

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 23/7

12:00-14:27

1 stop41h 27m

$1,295

Flights are sorted by cheapest return flights first.

Deals found on 5/5

Showing 1-10 of 17 resultsSorted by cheapest first
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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 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 $2,038.

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 $2,349. 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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