Find flights
When to book
Airlines
FAQs

Cheap flights from Chicago Midway Airport to Sydney from $1,472

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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SYD
7 Aug — 14 Aug1
1 adult

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 2 August 2025.

Round-trip from

$2,272

One-way from

$1,320

Popular in

December

Cheapest in

August

Average price

$1,329
Delta
  • Delta
  • 6/10-19/10
  • 4 total stops
  • 49h 47m total
  • Chicago to Sydney
Search Deals
Delta
  • Delta
  • 5/11
  • 2 total stops
  • 26h 22m total
  • Chicago to Sydney
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($432 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($97 potential savings vs. average return price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 2 August 2025.

Mon 6/1013:48MDW - SYD
2 stops25h 47mDelta
Sun 19/1010:25SYD - MDW
2 stops24h 00mDelta
Deal found 31/7$2,272
Thu 28/815:52MDW - SYD
2 stops39h 18mMultiple Airlines
Thu 4/912:10SYD - MDW
1 stop40h 01mMultiple Airlines
Deal found 31/7$2,825

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 2 August 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

Mon 6/10

13:48-07:35

2 stops25h 47m

Sydney Kingsford Smith

Sun 19/10

10:25-18:25

2 stops24h 00m

$2,272

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 28/8

15:52-22:10

2 stops39h 18m

Sydney Kingsford Smith

Thu 4/9

12:10-13:11

1 stop40h 01m

$2,825

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 1/9

13:08-06:35

2 stops26h 27m

$1,472

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 26/8

17:20-20:10

2 stops35h 50m

$1,692

Flights are sorted by cheapest return flights first.

Deals found on 31/7

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.

Reviews of airlines servicing Sydney

Get insights into the airlines that provide service to Sydney. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Sydney. Reviews last updated 2 August 2025.
Read reviews from past customers who have flown with Delta from Chicago Midway Airport to Sydney. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very Good
7,983 reviews
Check prices

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very Good
7,983 reviews
Delta
8.0
Very Good
7,983 reviews
Check prices

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What is the cheapest airline to fly from Chicago Midway Airport to Sydney round-trip?

    Flying on Delta is currently your cheapest option to Sydney, with prices starting at $2,272.

  • 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
Coogee
Terrigal
Cronulla
Lithgow
Bondi Beach
Randwick
Leura

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.