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Cheap flights from Chicago Midway Airport to Sydney from $884

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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SYD
29 Aug — 5 Sep1
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 30 July 2026.

Sun 18/1009:29
MDW
-
SYD
2 stops30h 21m
Delta
Sat 24/1010:15
SYD
-
MDW
2 stops28h 18m
Delta
Deal found 26/7$1,763
Sat 7/1110:01
MDW
-
SYD
2 stops29h 29m
Delta
Fri 13/1110:40
SYD
-
MDW
2 stops22h 59m
Delta
Deal found 25/7$1,835
Tue 25/806:05
MDW
-
SYD
3 stops46h 05m
Multiple Airlines
Tue 1/911:45
SYD
-
MDW
3 stops38h 10m
Multiple Airlines
Deal found 26/7$1,927
Thu 20/806:05
MDW
-
SYD
3 stops46h 05m
Multiple Airlines
Sat 29/811:45
SYD
-
MDW
3 stops38h 10m
Multiple Airlines
Deal found 27/7$1,943
Tue 4/806:05
MDW
-
SYD
2 stops34h 00m
Multiple Airlines
Wed 19/809:10
SYD
-
MDW
2 stops40h 45m
Multiple Airlines
Deal found 27/7$1,996
Tue 4/806:05
MDW
-
SYD
2 stops34h 00m
Multiple Airlines
Sun 16/809:10
SYD
-
MDW
2 stops39h 41m
Multiple Airlines
Deal found 27/7$2,079
Tue 11/811:06
MDW
-
SYD
2 stops28h 59m
Multiple Airlines
Sun 23/809:10
SYD
-
MDW
2 stops26h 21m
Multiple Airlines
Deal found 27/7$2,097
Wed 18/1109:30
MDW
-
SYD
2 stops30h 00m
Delta
Mon 7/1210:40
SYD
-
MDW
2 stops22h 59m
Delta
Deal found 26/7$2,112
Tue 1/910:54
MDW
-
SYD
2 stops28h 56m
Delta
Tue 8/909:15
SYD
-
MDW
2 stops24h 04m
Delta
Deal found 26/7$2,114
Sat 22/813:51
MDW
-
SYD
2 stops25h 59m
Delta
Fri 4/909:15
SYD
-
MDW
2 stops24h 18m
Delta
Deal found 25/7$2,186
Mon 21/913:19
MDW
-
SYD
2 stops26h 31m
Delta
Wed 7/1010:15
SYD
-
MDW
2 stops23h 45m
Delta
Deal found 27/7$2,297
Tue 29/1211:20
MDW
-
SYD
2 stops28h 10m
Delta
Wed 3/210:40
SYD
-
MDW
2 stops24h 57m
Delta
Deal found 26/7$2,304

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 30 July 2026.

Round-trip from

$1,763

One-way from

$884

Popular in

September

Cheapest in

February

Average price

$2,222
Delta
  • Delta
  • 13/8-25/8
  • 4 total stops
  • 50h 43m total
  • Chicago to Sydney
Search Deals
11/8
  • 11/8
  • 3 total stops
  • 37h 29m total
  • Chicago to Sydney
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($216 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($37 potential savings vs. average return price).
Search Deals
Average for round-trip flights in July 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 30 July 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

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 13/8

13:25-06:50

2 stops26h 25m

Sydney Kingsford Smith

Tue 25/8

09:15-18:33

2 stops24h 18m

$1,763

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Fri 11/9

17:03-06:50

2 stops22h 47m

Sydney Kingsford Smith

Sun 20/9

09:15-22:44

2 stops28h 29m

$1,763

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 1/9

10:54-06:50

2 stops28h 56m

Sydney Kingsford Smith

Tue 8/9

09:15-18:19

2 stops24h 04m

$2,114

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 22/8

13:51-06:50

2 stops25h 59m

Sydney Kingsford Smith

Fri 4/9

09:15-18:33

2 stops24h 18m

$2,186

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 26/9

09:29-06:50

2 stops30h 21m

Sydney Kingsford Smith

Sat 17/10

10:15-16:47

2 stops22h 32m

$2,320

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 29/10

10:01-07:30

2 stops29h 29m

Sydney Kingsford Smith

Sat 14/11

10:40-16:39

2 stops22h 59m

$2,320

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 7/11

13:27-08:30

2 stops26h 03m

Sydney Kingsford Smith

Sat 14/11

10:40-16:39

2 stops22h 59m

$2,320

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 9/9

17:37-06:50

2 stops22h 13m

Sydney Kingsford Smith

Wed 16/9

09:15-22:44

2 stops28h 29m

$2,449
Fastest return journey

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Fri 11/9

17:03-06:50

2 stops22h 47m

Sydney Kingsford Smith

Fri 18/9

09:15-18:33

2 stops24h 18m

$2,535

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 12/9

17:37-06:50

2 stops22h 13m

Sydney Kingsford Smith

Sat 19/9

09:15-22:44

2 stops28h 29m

$2,535

Flights are sorted by cheapest return flights first.

Deals found on 28/7

Showing 1-10 of 20 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
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 26h 25m. 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
Manly
Lithgow
Cronulla
Randwick
Terrigal
Leura
Bondi Beach
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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