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Cheap flights from Chicago Midway Airport to Sydney from $813

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 20/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SYD
16 Oct — 23 Oct1
1 adult
1 adult, Economy

Cheap 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 16 September 2025.

Round-trip from

$1,550

One-way from

$813

Popular in

December

Cheapest in

August

Average price

$1,499
27/10-9/11
  • 27/10-9/11
  • 4 total stops
  • 53h 55m total
  • Chicago to Sydney
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20/10
  • 20/10
  • 2 total stops
  • 30h 21m total
  • Chicago to Sydney
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($413 potential increase over avg. return price).
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Cheapest flight prices on average. 3% potential price decrease ($83 potential savings vs. average return price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Sydney

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 16 September 2025.

Mon 27/1012:03MDW - SYD
2 stops28h 57mMultiple Airlines
Sun 9/1114:05SYD - MDW
2 stops24h 58mMultiple Airlines
Deal found 15/9$1,550
Mon 20/1009:44MDW - SYD
2 stops30h 21mMultiple Airlines
Sun 2/1114:05SYD - MDW
2 stops24h 58mMultiple Airlines
Deal found 15/9$1,609
Thu 30/1006:30MDW - SYD
2 stops34h 30mMultiple Airlines
Thu 6/1111:20SYD - MDW
2 stops41h 10mMultiple Airlines
Deal found 15/9$2,118
Thu 20/1105:30MDW - SYD
2 stops38h 30mMultiple Airlines
Fri 12/1214:05SYD - MDW
1 stop24h 23mMultiple Airlines
Deal found 13/9$2,160
Sun 16/1113:47MDW - SYD
2 stops25h 43mDelta
Tue 9/1210:40SYD - MDW
2 stops29h 52mDelta
Deal found 13/9$2,202
Sat 22/1119:02MDW - SYD
2 stops44h 28mDelta
Sun 7/1210:40SYD - MDW
2 stops29h 52mDelta
Deal found 13/9$2,229
Wed 31/1211:48MDW - SYD
2 stops27h 42mDelta
Fri 30/110:40SYD - MDW
2 stops28h 06mDelta
Deal found 15/9$2,277
Thu 6/1113:08MDW - SYD
2 stops26h 22mDelta
Sat 22/1110:40SYD - MDW
2 stops29h 52mDelta
Deal found 15/9$2,352
Sun 16/1111:21MDW - SYD
2 stops27h 04mMultiple Airlines
Fri 12/1214:05SYD - MDW
1 stop24h 23mMultiple Airlines
Deal found 13/9$2,358
Tue 21/1013:48MDW - SYD
2 stops25h 47mDelta
Tue 2/1210:40SYD - MDW
2 stops24h 38mDelta
Deal found 15/9$2,427
Sat 1/1109:20MDW - SYD
2 stops30h 10mDelta
Sun 16/1110:40SYD - MDW
2 stops24h 38mDelta
Deal found 15/9$2,502
Thu 25/1210:08MDW - SYD
2 stops29h 22mDelta
Tue 6/114:15SYD - MDW
2 stops24h 31mDelta
Deal found 13/9$2,569

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 16 September 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Sydney that are best for you.

Fly from

Midway

Fly to

Sydney

Route

Depart

Return

Price

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 30/10

06:30-09:00

2 stops34h 30m

Sydney Kingsford Smith

Thu 6/11

11:20-11:30

2 stops41h 10m

$2,118

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 3/3

13:00-06:50

2 stops24h 50m

Sydney Kingsford Smith

Wed 11/3

09:40-18:34

2 stops24h 54m

$2,202

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 18/1

10:35-06:50

2 stops27h 15m

Sydney Kingsford Smith

Tue 27/1

14:15-21:46

2 stops24h 31m

$2,202

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 9/12

09:34-08:30

2 stops29h 56m

Sydney Kingsford Smith

Tue 23/12

10:40-17:19

2 stops23h 39m

$2,202

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 10/11

13:47-08:30

2 stops25h 43m

Sydney Kingsford Smith

Wed 26/11

10:40-18:08

2 stops24h 28m

$2,202

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 18/11

13:47-08:30

2 stops25h 43m

Sydney Kingsford Smith

Mon 8/12

10:40-23:32

2 stops29h 52m

$2,202

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 19/11

13:14-08:30

2 stops26h 16m

Sydney Kingsford Smith

Tue 9/12

10:40-23:32

2 stops29h 52m

$2,202

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 18/11

12:47-08:30

2 stops26h 43m

Sydney Kingsford Smith

Tue 9/12

10:40-23:32

2 stops29h 52m

$2,202

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 19/11

13:14-08:30

2 stops26h 16m

Sydney Kingsford Smith

Sun 7/12

10:40-23:32

2 stops29h 52m

$2,202

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 16/11

12:47-08:30

2 stops26h 43m

Sydney Kingsford Smith

Wed 10/12

10:40-16:36

2 stops22h 56m

$2,202

Flights are sorted by cheapest return flights first.

Deals found on 14/9

Showing 1-10 of 20 results
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 24h 50m. 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Sydney?

    Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Sydney (average of $129). Flying from Chicago Midway Airport to Sydney in October is currently the most expensive (average of $171). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Travelling to a place near Sydney?

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

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

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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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