Find flights
When to book
FAQs

Cheap flights from Chicago Midway Airport to Sydney from $761

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 28/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SYD
10 May — 17 May1
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 10 April 2026.

Tue 21/406:10
MDW
-
SYD
2 stops33h 55m
Multiple Airlines
Sun 10/517:50
SYD
-
MDW
2 stops32h 19m
Multiple Airlines
Deal found 6/4$1,882
Tue 28/406:10
MDW
-
SYD
2 stops33h 55m
Multiple Airlines
Sun 17/509:10
SYD
-
MDW
2 stops44h 02m
Multiple Airlines
Deal found 8/4$1,912
Tue 5/506:00
MDW
-
SYD
2 stops34h 05m
Multiple Airlines
Sun 31/517:50
SYD
-
MDW
2 stops35h 22m
Multiple Airlines
Deal found 7/4$1,919
Tue 5/506:00
MDW
-
SYD
2 stops34h 05m
Multiple Airlines
Sun 17/517:50
SYD
-
MDW
2 stops35h 22m
Multiple Airlines
Deal found 10/4$1,979
Sun 24/506:00
MDW
-
SYD
3 stops38h 50m
Multiple Airlines
Sun 31/513:15
SYD
-
MDW
3 stops39h 57m
Multiple Airlines
Deal found 6/4$2,057
Thu 23/408:26
MDW
-
SYD
2 stops32h 04m
Multiple Airlines
Sun 10/509:10
SYD
-
MDW
2 stops40h 59m
Multiple Airlines
Deal found 10/4$2,086
Tue 1/913:00
MDW
-
SYD
2 stops26h 50m
Delta
Tue 8/909:15
SYD
-
MDW
2 stops24h 16m
Delta
Deal found 7/4$2,282
Thu 24/910:35
MDW
-
SYD
2 stops29h 15m
Delta
Tue 6/1010:15
SYD
-
MDW
2 stops22h 35m
Delta
Deal found 10/4$2,286
Sat 26/1217:25
MDW
-
SYD
2 stops46h 05m
Delta
Wed 6/110:40
SYD
-
MDW
2 stops39h 09m
Delta
Deal found 6/4$2,312
Tue 12/506:00
MDW
-
SYD
2 stops34h 05m
Multiple Airlines
Thu 28/509:10
SYD
-
MDW
2 stops40h 59m
Multiple Airlines
Deal found 7/4$2,322
Mon 1/610:59
MDW
-
SYD
2 stops28h 51m
Delta
Mon 15/609:15
SYD
-
MDW
2 stops24h 03m
Delta
Deal found 6/4$2,343

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 10 April 2026.

Round-trip from

$1,882

One-way from

$761

Popular in

July

Cheapest in

February

Average price

$2,058
21/4-10/5
  • 21/4-10/5
  • 4 total stops
  • 66h 14m total
  • Chicago to Sydney
Search Deals
28/5
  • 28/5
  • 2 total stops
  • 40h 03m total
  • Chicago to Sydney
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($127 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($41 potential savings vs. average return price).
Search Deals
Average for round-trip flights in April 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 10 April 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 1/6

10:59-06:50

2 stops28h 51m

Sydney Kingsford Smith

Mon 15/6

09:15-18:18

2 stops24h 03m

$2,282

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 29/6

12:45-06:50

2 stops27h 05m

Sydney Kingsford Smith

Mon 13/7

09:15-18:18

2 stops24h 03m

$2,282

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 29/7

13:16-06:50

2 stops26h 34m

Sydney Kingsford Smith

Tue 11/8

09:15-18:05

2 stops23h 50m

$2,282

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 8/8

13:16-06:50

2 stops26h 34m

Sydney Kingsford Smith

Sat 22/8

09:15-18:05

2 stops23h 50m

$2,282

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 31/5

09:22-06:50

2 stops30h 28m

Sydney Kingsford Smith

Tue 16/6

09:15-18:18

2 stops24h 03m

$2,282

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 13/7

09:49-06:50

2 stops30h 01m

Sydney Kingsford Smith

Wed 29/7

09:15-22:15

2 stops28h 00m

$2,282

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 4/7

13:16-06:50

2 stops26h 34m

Sydney Kingsford Smith

Fri 31/7

09:15-18:25

2 stops24h 10m

$2,286
Fastest return journey

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 1/8

13:16-06:50

2 stops26h 34m

Sydney Kingsford Smith

Sat 8/8

09:15-18:02

2 stops23h 47m

$2,286

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 2/5

06:00-07:05

2 stops34h 05m

Sydney Kingsford Smith

Mon 11/5

17:50-11:09

2 stops32h 19m

$2,346

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 6/5

12:52-06:50

2 stops26h 58m

Sydney Kingsford Smith

Wed 13/5

09:15-17:56

2 stops23h 41m

$2,404

Flights are sorted by cheapest return flights first.

Deals found on 5/4

Showing 1-10 of 18 resultsSorted by cheapest first
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 28h 51m. 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
Terrigal
Katoomba
Lithgow
Cronulla
Manly
Bondi Beach
Coogee
Leura
Randwick

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.