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Cheap flights from Chicago Midway Airport to Sydney from $1,086

MDW — SYD
26 Nov — 3 Dec1
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

Fri 23/1013:27 -
2 stops26h 23m
Fri 30/1009:40 -
2 stops23h 07m
Deal found 22/10$1,856
Sat 7/1110:12 -
2 stops29h 18m
Fri 13/1110:40 -
2 stops22h 59m
Deal found 23/10$1,858
Thu 19/1106:08 -
2 stops31h 17m
Thu 26/1114:00 -
3 stops35h 12m
Deal found 22/10$2,135
Mon 26/1006:15 -
3 stops34h 20m
Sun 8/1107:30 -
3 stops33h 17m
Deal found 22/10$2,270
Thu 29/1006:16 -
2 stops32h 09m
Thu 5/1111:15 -
2 stops29h 32m
Deal found 22/10$2,330
Sun 8/1113:27 -
2 stops26h 03m
Wed 18/1110:40 -
2 stops22h 59m
Deal found 26/10$2,428
Tue 27/1012:27 -
1 stop26h 28m
Mon 16/1108:45 -
2 stops43h 37m
Deal found 26/10$2,962
Mon 9/1112:20 -
1 stop25h 35m
Wed 25/1115:15 -
2 stops57h 22m
Deal found 24/10$2,991
Mon 7/1215:45 -
2 stops35h 30m
Mon 14/1221:45 -
2 stops49h 10m
Deal found 23/10$3,365

Find flight deals from Midway to Sydney

Round-trip from

$1,856

One-way from

$1,086

Popular in

December

Cheapest in

February

Average price

$2,285
Delta
  • Delta
  • 7/11-13/11
  • 4 total stops
  • 52h 17m total
  • Chicago to Sydney
Search Deals
26/2-31/12
  • 26/2-31/12
  • 3 total stops
  • 59h 44m total
  • Chicago to Sydney
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($118 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($77 potential savings vs. average return price).
Search Deals
Average for round-trip flights in October 2026
Search Deals

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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Cheapest return flight

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Fri 26/2

06:01-10:45

3 stops59h 44m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$1,086

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Mon 28/12

13:11-06:35

2 stops48h 24m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$1,536

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Sun 1/11

12:20-07:15

2 stops49h 55m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$1,641

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Sun 17/1

13:18-17:30

3 stops59h 12m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$1,701

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Sat 7/11

10:12-08:30

2 stops29h 18m

Sydney Kingsford Smith

Fri 13/11

10:40-16:39

2 stops22h 59m

$1,858

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Wed 23/12

09:30-08:30

2 stops30h 00m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$2,416

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Wed 23/12

14:00-12:15

2 stops53h 15m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$2,528
Fastest return journey

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Sun 27/12

12:55-06:50

2 stops24h 55m

Sydney Kingsford Smith

Wed 31/12

00:00-08:00

Nonstop0h 00m

$2,689

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Wed 17/3

15:50-12:15

2 stops52h 25m

Sydney Kingsford Smith

Wed 31/3

22:10-06:05

2 stops47h 55m

$3,549

ChicagoSydney

MDW Chicago Midway - SYD Sydney Kingsford Smith

MDWSYD

Chicago Midway

Fri 2/4

18:20-11:45

2 stops49h 25m

Sydney Kingsford Smith

Fri 16/4

22:10-06:05

2 stops46h 55m

$3,749

Flights are sorted by cheapest return flights first.

Deals found on 22/10

Showing 1-10 of 17 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 29h 18m. 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
Cronulla
Lithgow
Terrigal
Katoomba
Randwick
Leura
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.

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

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