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Cheap flights from Chicago Midway Airport to Sydney from $833

MDW — SYD
11 Oct — 18 Oct1
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

Mon 14/906:25 -
2 stops33h 40m
Mon 21/909:10 -
2 stops29h 34m
Deal found 6/9$2,007
Sun 13/906:25 -
2 stops33h 40m
Mon 16/1111:10 -
2 stops29h 37m
Deal found 7/9$2,025
Fri 23/1006:15 -
2 stops32h 10m
Thu 5/1111:10 -
2 stops29h 37m
Deal found 9/9$2,031
Sat 26/906:25 -
2 stops33h 40m
Sat 17/1010:10 -
2 stops29h 33m
Deal found 10/9$2,092
Sun 18/1013:12 -
2 stops26h 53m
Sun 1/1111:10 -
2 stops29h 37m
Deal found 9/9$2,127
Wed 30/906:25 -
2 stops33h 40m
Wed 21/1010:10 -
2 stops29h 33m
Deal found 7/9$2,219
Wed 25/1118:05 -
2 stops33h 10m
Sun 6/1221:45 -
2 stops49h 10m
Deal found 6/9$2,242
Sun 1/1109:29 -
2 stops30h 01m
Sun 8/1110:40 -
2 stops24h 20m
Deal found 10/9$2,246
Tue 29/1211:47 -
2 stops27h 43m
Sat 23/110:40 -
2 stops28h 30m
Deal found 10/9$2,249
Tue 15/913:00 -
2 stops26h 50m
Mon 21/909:15 -
2 stops24h 04m
Deal found 10/9$2,251

Find flight deals from Midway to Sydney

Round-trip from

$2,031

One-way from

$833

Popular in

December

Cheapest in

June

Average price

$2,233
23/10-5/11
  • 23/10-5/11
  • 4 total stops
  • 61h 47m total
  • Chicago to Sydney
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24/10-31/12
  • 24/10-31/12
  • 2 total stops
  • 46h 55m total
  • Chicago to Sydney
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($113 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($28 potential savings vs. average return price).
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Average for round-trip flights in September 2026
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Cheapflights Fare Finder

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

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Route

Depart

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Price

Cheapest return flight

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Sat 24/10

06:21-20:45

3 stops46h 24m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$942

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Tue 17/11

06:16-19:45

3 stops44h 29m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$1,129

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Wed 2/12

21:23-20:15

3 stops53h 52m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$1,234

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Tue 3/11

11:39-08:30

2 stops27h 51m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$1,284

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Mon 2/11

11:38-08:30

2 stops27h 52m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$1,284
Fastest return journey

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Wed 28/10

12:27-07:30

2 stops27h 03m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$1,284

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Fri 6/11

10:12-08:30

2 stops29h 18m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$1,285

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Mon 5/10

09:29-07:50

2 stops30h 21m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$1,429

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Fri 1/1

09:58-08:30

2 stops29h 32m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$1,796

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Thu 7/1

06:00-08:30

2 stops33h 30m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$1,797

Flights are sorted by cheapest return flights first.

Deals found on 9/9

Showing 1-10 of 22 resultsSorted by cheapest first
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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

Related info for your journey

  • 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 27h 48m. 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
Manly
Katoomba
Lithgow
Cronulla
Terrigal
Leura
Randwick
Bondi Beach
Coogee

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Midway to Sydney

O'Hare Intl to Sydney flights

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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.

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