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Cheap flights from Chicago Midway Airport to Sydney from $1,003

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 15/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SYD
14 Jul — 21 Jul1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Midway to Sydney

Enter your travel dates to find the best prices.

Cheapest flights from Midway to Sydney
Explore the most affordable flight options available from Midway to Sydney. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 14 Juni 2026.

Mi 5/812:46
MDW
-
SYD
2 stops27h 04m
Delta
So 30/809:15
SYD
-
MDW
2 stops23h 46m
Delta
Deal found 12/6$2,287
Mo 27/706:05
MDW
-
SYD
2 stops33h 50m
Multiple Airlines
Mo 3/812:00
SYD
-
MDW
1 stop20h 22m
Multiple Airlines
Deal found 12/6$2,363
Mo 24/813:27
MDW
-
SYD
2 stops26h 23m
Delta
Mi 2/909:15
SYD
-
MDW
2 stops28h 21m
Delta
Deal found 9/6$2,394
Mo 27/713:49
MDW
-
SYD
2 stops26h 01m
Delta
Mo 3/809:15
SYD
-
MDW
2 stops23h 46m
Delta
Deal found 12/6$2,499
Sa 25/709:54
MDW
-
SYD
2 stops29h 56m
Delta
Sa 1/809:15
SYD
-
MDW
2 stops23h 37m
Delta
Deal found 10/6$2,501
Mi 9/1213:05
MDW
-
SYD
2 stops26h 25m
Delta
Mo 11/110:40
SYD
-
MDW
2 stops24h 57m
Delta
Deal found 13/6$2,582
Di 1/1213:05
MDW
-
SYD
2 stops26h 25m
Delta
So 13/1210:40
SYD
-
MDW
2 stops24h 57m
Delta
Deal found 10/6$2,583
Mi 26/813:27
MDW
-
SYD
2 stops26h 23m
Delta
Di 8/909:15
SYD
-
MDW
2 stops24h 04m
Delta
Deal found 14/6$2,653
So 21/613:49
MDW
-
SYD
2 stops26h 01m
Delta
Di 7/709:15
SYD
-
MDW
2 stops24h 03m
Delta
Deal found 12/6$2,695

Find flight deals from Midway to Sydney

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Sydney (SYD). 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 14 Juni 2026.

Round-trip from

$2,287

One-way from

$1,003

Popular in

December

Cheapest in

February

Average price

$1,963
Delta
  • Delta
  • 5/8-30/8
  • 4 total stops
  • 50h 50m total
  • Chicago to Sydney
Search Deals
15/9
  • 15/9
  • 3 total stops
  • 44h 45m total
  • Chicago to Sydney
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($89 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($39 potential savings vs. average return price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from Midway to Sydney 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 14 Juni 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Sydney that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight
Fastest return journey

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Di 1/9

13:51-06:50

2 stops25h 59m

Sydney Kingsford Smith

Di 8/9

09:15-18:05

2 stops23h 50m

$2,287

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sa 15/8

13:51-06:50

2 stops25h 59m

Sydney Kingsford Smith

Sa 22/8

09:15-18:33

2 stops24h 18m

$2,287

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mi 14/10

13:05-07:50

2 stops26h 45m

Sydney Kingsford Smith

Mo 26/10

09:40-16:50

2 stops23h 10m

$2,288

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mi 14/10

13:05-07:50

2 stops26h 45m

Sydney Kingsford Smith

Mi 28/10

09:40-16:50

2 stops23h 10m

$2,288

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Do 10/9

13:00-06:50

2 stops26h 50m

Sydney Kingsford Smith

Do 17/9

09:15-18:11

2 stops23h 56m

$2,288

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sa 22/8

13:27-06:50

2 stops26h 23m

Sydney Kingsford Smith

Fr 4/9

09:15-22:36

2 stops28h 21m

$2,288

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Di 28/7

06:00-06:50

2 stops33h 50m

Sydney Kingsford Smith

Di 4/8

09:15-09:17

2 stops39h 02m

$2,499
Cheapest one-way

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Di 15/9

07:25-19:10

3 stops44h 45m

$1,003

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sa 22/8

15:02-07:30

3 stops49h 28m

$1,040

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

So 13/9

07:25-06:55

2 stops32h 30m

$1,061

Flights are sorted by cheapest return flights first.

Deals found on 11/6

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

Best time to book a flight from Midway to Sydney

Have a flexible travel schedule? Discover the best time to fly to Sydney from Midway 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 Midway to Sydney. 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 into for flights to Sydney from Chicago Midway?

    Sydney Kingsford Smith (SYD) is the airport you will fly into if you book a flight from Chicago Midway to Sydney. You should not have trouble finding flights to Kingsford Smith from Chicago Midway; the airport handles an average of 0 inbound flights from Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the Sydney airport from Chicago Midway. It is only a 7.5 km journey from Kingsford Smith (SYD) to Sydney’s city centre.

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

    Airlines like Delta fly from Chicago Midway Airport to Sydney in about 25h 59m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 14861 km.

  • Can I find deals for flights from Midway to Sydney that include hotel bookings?

    Yes. In addition to deals on Midway to Sydney flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Midway to Sydney?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Sydney.

  • Can I find deals for business class flights from Midway to Sydney?

    Yes. Cheapflights offers flight deals from Midway to Sydney 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

Travelling to a place near Sydney?

Book flights to Sydney if you plan to visit one of these locations
Parramatta
Wollongong
Penrith
Katoomba
Cronulla
Manly
Terrigal
Lithgow
Randwick
Bondi Beach
Leura
Coogee

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Midway to Sydney

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

Cheapflights makes it easy to find Midway to Sydney flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Midway to Sydney.

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

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

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

Yes! Start tracking prices for Midway to Sydney flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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