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Cheap flights from Chicago Midway Airport to Sydney from $1,107

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 30/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SYD
15 Jan — 22 Jan1
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 16 December 2025.

Fri 26/1206:00MDW - SYD
2 stops33h 30mDelta
Wed 21/110:40SYD - MDW
2 stops23h 49mDelta
Deal found 15/12$2,735
Thu 25/1209:29MDW - SYD
2 stops30h 01mDelta
Sun 11/110:40SYD - MDW
2 stops23h 57mDelta
Deal found 15/12$3,076
Wed 24/1209:29MDW - SYD
2 stops30h 01mDelta
Tue 6/110:40SYD - MDW
2 stops24h 52mDelta
Deal found 13/12$3,339
Thu 25/1209:50MDW - SYD
2 stops29h 40mDelta
Tue 6/110:40SYD - MDW
2 stops24h 52mDelta
Deal found 14/12$3,414
Tue 23/1209:50MDW - SYD
2 stops28h 00mDelta
Tue 6/110:40SYD - MDW
2 stops24h 52mDelta
Deal found 15/12$3,423
Wed 24/1209:50MDW - SYD
2 stops29h 40mDelta
Wed 28/110:40SYD - MDW
2 stops23h 49mDelta
Deal found 15/12$3,519
Wed 24/1209:29MDW - SYD
2 stops30h 01mDelta
Wed 31/1210:40SYD - MDW
2 stops28h 42mDelta
Deal found 14/12$3,586
Wed 24/1209:50MDW - SYD
2 stops29h 40mDelta
Mon 12/110:40SYD - MDW
2 stops23h 54mDelta
Deal found 15/12$3,784
Mon 15/1213:50MDW - SYD
2 stops25h 40mDelta
Mon 19/110:40SYD - MDW
2 stops24h 15mDelta
Deal found 15/12$3,864
Tue 16/1213:50MDW - SYD
2 stops25h 40mDelta
Wed 31/1210:40SYD - MDW
2 stops28h 42mDelta
Deal found 16/12$3,939

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 16 December 2025.

Round-trip from

$1,742

One-way from

$1,107

Popular in

December

Cheapest in

August

Average price

$2,088
Delta
  • Delta
  • 1/2-15/2
  • 4 total stops
  • 53h 26m total
  • Chicago to Sydney
Search Deals
30/1
  • 30/1
  • 2 total stops
  • 44h 54m total
  • Chicago to Sydney
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($416 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($91 potential savings vs. average return price).
Search Deals
Average for round-trip flights in December 2025
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 16 December 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

Sun 1/2

13:26-06:50

2 stops24h 24m

Sydney Kingsford Smith

Sun 15/2

10:40-22:42

2 stops29h 02m

$1,742

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 9/2

13:51-08:30

2 stops25h 39m

Sydney Kingsford Smith

Mon 16/2

10:40-17:45

2 stops24h 05m

$1,757

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 28/1

13:26-08:30

2 stops26h 04m

Sydney Kingsford Smith

Mon 9/2

10:40-17:29

2 stops23h 49m

$1,757

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 1/2

12:48-08:30

2 stops26h 42m

Sydney Kingsford Smith

Wed 18/2

10:40-17:37

2 stops23h 57m

$1,757

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 31/3

12:47-07:35

2 stops26h 48m

Sydney Kingsford Smith

Wed 15/4

09:15-18:05

2 stops23h 50m

$1,757

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 8/2

13:26-06:50

2 stops24h 24m

Sydney Kingsford Smith

Tue 10/3

09:40-16:53

2 stops23h 13m

$1,757

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 10/2

13:26-08:30

2 stops26h 04m

Sydney Kingsford Smith

Tue 3/3

10:40-17:45

2 stops24h 05m

$1,757

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 15/3

12:47-07:25

2 stops26h 38m

Sydney Kingsford Smith

Sun 29/3

10:15-17:55

2 stops23h 40m

$1,757

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 28/1

09:33-08:30

2 stops29h 57m

Sydney Kingsford Smith

Wed 4/2

10:40-17:29

2 stops23h 49m

$1,757

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 10/2

13:26-06:50

2 stops24h 24m

Sydney Kingsford Smith

Tue 17/2

14:15-22:44

2 stops25h 29m

$1,757

Flights are sorted by cheapest return flights first.

Deals found on 14/12

Showing 1-10 of 18 results
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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 24h 24m. 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
Katoomba
Penrith
Terrigal
Manly
Randwick
Lithgow
Coogee
Leura
Cronulla
Bondi Beach

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

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.

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