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Cheap flights from Chicago Midway Airport to Sydney from $788

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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SYD
31 May — 7 Jun1
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 1 May 2026.

Thu 7/515:07
MDW
-
SYD
2 stops29h 43m
Multiple Airlines
Tue 12/512:00
SYD
-
MDW
1 stop41h 12m
Multiple Airlines
Deal found 29/4$2,055
Wed 27/506:00
MDW
-
SYD
2 stops34h 05m
Multiple Airlines
Sun 7/609:10
SYD
-
MDW
2 stops40h 59m
Multiple Airlines
Deal found 28/4$2,111
Sat 16/515:07
MDW
-
SYD
2 stops29h 43m
Multiple Airlines
Wed 10/612:00
SYD
-
MDW
1 stop42h 15m
Multiple Airlines
Deal found 30/4$2,174
Wed 5/813:49
MDW
-
SYD
2 stops26h 01m
Delta
Sun 30/809:15
SYD
-
MDW
2 stops24h 16m
Delta
Deal found 28/4$2,453
Wed 26/813:00
MDW
-
SYD
2 stops26h 50m
Delta
Wed 2/909:15
SYD
-
MDW
2 stops24h 16m
Delta
Deal found 28/4$2,558
Sat 22/814:00
MDW
-
SYD
2 stops25h 50m
Delta
Fri 4/909:15
SYD
-
MDW
2 stops27h 31m
Delta
Deal found 28/4$2,568
Mon 17/813:00
MDW
-
SYD
2 stops26h 50m
Delta
Sat 5/909:15
SYD
-
MDW
2 stops24h 16m
Delta
Deal found 30/4$2,569
Thu 28/513:22
MDW
-
SYD
2 stops26h 28m
Delta
Mon 8/609:15
SYD
-
MDW
2 stops24h 16m
Delta
Deal found 28/4$2,682
Tue 9/612:45
MDW
-
SYD
2 stops27h 05m
Delta
Thu 25/609:15
SYD
-
MDW
2 stops24h 03m
Delta
Deal found 29/4$2,683
Fri 3/711:05
MDW
-
SYD
2 stops28h 45m
Delta
Sat 11/709:15
SYD
-
MDW
2 stops23h 37m
Delta
Deal found 26/4$2,742
Thu 30/406:00
MDW
-
SYD
2 stops34h 05m
Multiple Airlines
Wed 6/509:10
SYD
-
MDW
2 stops40h 59m
Multiple Airlines
Deal found 28/4$2,760

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 1 May 2026.

Round-trip from

$2,111

One-way from

$788

Popular in

July

Cheapest in

February

Average price

$2,021
27/5-7/6
  • 27/5-7/6
  • 4 total stops
  • 75h 04m total
  • Chicago to Sydney
Search Deals
6/6
  • 6/6
  • 3 total stops
  • 48h 03m total
  • Chicago to Sydney
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($118 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($38 potential savings vs. average return price).
Search Deals
Average for round-trip flights in May 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 1 May 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

Mon 29/6

09:54-06:50

2 stops29h 56m

Sydney Kingsford Smith

Tue 7/7

09:15-18:18

2 stops24h 03m

$2,453

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 8/7

12:41-06:50

2 stops27h 09m

Sydney Kingsford Smith

Sat 25/7

09:15-17:52

2 stops23h 37m

$2,453

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 6/7

09:54-06:50

2 stops29h 56m

Sydney Kingsford Smith

Mon 27/7

09:15-18:18

2 stops24h 03m

$2,454

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 1/6

12:53-06:50

2 stops26h 57m

Sydney Kingsford Smith

Mon 15/6

09:15-18:31

2 stops24h 16m

$2,682
Fastest return journey

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 24/5

13:22-06:50

2 stops26h 28m

Sydney Kingsford Smith

Thu 4/6

09:15-17:56

2 stops23h 41m

$2,682

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 28/5

12:53-06:50

2 stops26h 57m

Sydney Kingsford Smith

Mon 8/6

09:15-18:31

2 stops24h 16m

$2,682

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 9/6

12:45-06:50

2 stops27h 05m

Sydney Kingsford Smith

Tue 16/6

09:15-18:18

2 stops24h 03m

$2,682

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 11/6

13:49-06:50

2 stops26h 01m

Sydney Kingsford Smith

Thu 18/6

09:15-18:31

2 stops24h 16m

$2,682

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 23/5

13:59-06:50

2 stops25h 51m

Sydney Kingsford Smith

Sat 30/5

09:15-21:09

2 stops26h 54m

$2,682
Cheapest one-way

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 21/7

06:00-11:50

3 stops38h 50m

$824

Flights are sorted by cheapest return flights first.

Deals found on 28/4

Showing 1-10 of 18 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 29h 56m. 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
Terrigal
Lithgow
Cronulla
Manly
Bondi Beach
Leura
Randwick
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

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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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