HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Sydney

$582+ Cheap flights from Midway (MDW) to Sydney (SYD)

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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SYD
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Sydney with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 20, 2025.

This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:48 amMDW - SYD
2 stops26h 02mDelta
Sun 2/110:40 amSYD - MDW
2 stops28h 06mDelta
Deal found 10/19$1,465
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/71:14 pmMDW - SYD
2 stops26h 16mDelta
Sat 12/2710:40 amSYD - MDW
2 stops23h 39mDelta
Deal found 10/18$1,515
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amMDW - SYD
2 stops33h 30mDelta
Fri 1/3010:40 amSYD - MDW
2 stops28h 06mDelta
Deal found 10/18$1,516
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/91:14 pmMDW - SYD
2 stops26h 16mDelta
Fri 12/1910:40 amSYD - MDW
2 stops30h 07mDelta
Deal found 10/18$1,590
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:00 amMDW - SYD
2 stops33h 30mDelta
Wed 1/2810:40 amSYD - MDW
2 stops24h 54mDelta
Deal found 10/20$1,615
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/29:59 amMDW - SYD
2 stops29h 31mDelta
Tue 12/910:40 amSYD - MDW
2 stops30h 09mDelta
Deal found 10/18$1,616
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2910:47 amMDW - SYD
2 stops28h 43mDelta
Fri 12/1910:40 amSYD - MDW
2 stops22h 51mDelta
Deal found 10/19$1,715
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:00 amMDW - SYD
2 stops33h 30mDelta
Fri 11/2110:40 amSYD - MDW
2 stops30h 00mDelta
Deal found 10/17$1,716
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/211:48 pmMDW - SYD
2 stops25h 47mDelta
Tue 12/210:40 amSYD - MDW
2 stops24h 38mDelta
Deal found 10/18$1,765
This Kiwi.com deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1412:30 pmMDW - SYD
2 stops49h 55mMultiple Airlines
Fri 11/212:05 pmSYD - MDW
1 stop28h 00mMultiple Airlines
Deal found 10/17$1,782
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/239:29 amMDW - SYD
2 stops28h 21mDelta
Mon 1/122:15 pmSYD - MDW
2 stops24h 31mDelta
Deal found 10/19$1,815

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 October 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$1,465
(Delta)

One-way from

$582
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$907
Provider with most accurate pricing for Chicago Midway-Sydney Kingsford Smith flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Sydney Kingsford Smith flights.
Search Deals
From Chicago Midway to Sydney Kingsford Smith
Search Deals
One-way flight from Chicago Midway to Sydney Kingsford Smith
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($197 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize 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 2,558,603 searches. Data last updated October 20, 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

Tue 12/30

9:50 am-6:50 am

2 stops28h 00m

Sydney Kingsford Smith

Tue 2/3

2:15 pm-9:46 pm

2 stops24h 31m

$1,465

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 12/31

6:00 am-8:30 am

2 stops33h 30m

Sydney Kingsford Smith

Tue 1/20

2:15 pm-9:46 pm

2 stops24h 31m

$1,465

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 12/30

12:45 pm-6:50 am

2 stops25h 05m

Sydney Kingsford Smith

Wed 2/4

10:40 am-9:46 pm

2 stops28h 06m

$1,465

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 12/30

11:48 am-6:50 am

2 stops26h 02m

Sydney Kingsford Smith

Sun 2/1

10:40 am-9:46 pm

2 stops28h 06m

$1,465

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 12/7

12:50 pm-8:30 am

2 stops26h 40m

Sydney Kingsford Smith

Sun 12/21

10:40 am-4:24 pm

2 stops22h 44m

$1,465

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 12/31

6:00 am-8:30 am

2 stops33h 30m

Sydney Kingsford Smith

Fri 1/30

10:40 am-9:46 pm

2 stops28h 06m

$1,515

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Fri 1/16

9:30 am-8:30 am

2 stops30h 00m

Sydney Kingsford Smith

Tue 2/10

10:40 am-9:46 pm

2 stops28h 06m

$1,516

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Fri 1/16

9:30 am-8:30 am

2 stops30h 00m

Sydney Kingsford Smith

Thu 2/5

2:15 pm-9:46 pm

2 stops24h 31m

$1,565

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 12/9

1:14 pm-8:30 am

2 stops26h 16m

Sydney Kingsford Smith

Fri 12/19

10:40 am-11:47 pm

2 stops30h 07m

$1,590

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 11/15

1:37 pm-7:25 am

3 stops48h 48m

$582

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

Showing 1-10 of 19 results
1
2

Compare providers for flights from Midway to Sydney

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Sydney in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Sydney flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Sydney flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Sydney flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Sydney flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Sydney flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 round-trip 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?

    For a flight from Chicago Midway to Sydney, you will be flying into Kingsford Smith. Sydney Kingsford Smith (SYD) is just 4.6 mi from the center of the city. Kingsford Smith is the only Sydney airport and it handles 0 inbound flights from Chicago Midway per day. 0 airlines have flights to Sydney Kingsford Smith from Chicago Midway on a regular basis.

  • How long is the flight from Chicago Midway Airport to Sydney?

    Departing from Chicago Midway Airport to Sydney will take you 28h. The distance between Chicago Midway Airport and Sydney is about 9234 mi.

  • 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 vacation 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

Traveling to a place near Sydney?

Book flights to Sydney if you plan to visit one of these locations
Parramatta
Wollongong
Manly
Coogee

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
O'Hare Intl to Coolangatta flights

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.