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Cheap flights from Chicago Midway Airport to Sydney from $1,156

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 1/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SYD
30 nov — 7 dic1
1 adult
1 adult, Economy, 0 bags

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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 31 ottobre 2025.

gio 13/1109:00MDW - SYD
2 stops31h 00mMultiple Airlines
gio 20/1117:45SYD - MDW
2 stops37h 55mMultiple Airlines
Deal found 29/10$1,731
dom 7/1206:15MDW - SYD
2 stops33h 45mMultiple Airlines
dom 14/1217:45SYD - MDW
2 stops34h 23mMultiple Airlines
Deal found 29/10$1,736
sab 1/1113:11MDW - SYD
2 stops26h 19mDelta
dom 16/1110:40SYD - MDW
2 stops22h 58mDelta
Deal found 30/10$2,009
ven 14/1109:41MDW - SYD
2 stops29h 49mDelta
sab 22/1110:40SYD - MDW
2 stops24h 28mDelta
Deal found 30/10$2,085
dom 30/1113:47MDW - SYD
2 stops25h 43mDelta
dom 7/1210:40SYD - MDW
2 stops30h 07mDelta
Deal found 28/10$2,461
dom 30/1106:00MDW - SYD
2 stops33h 30mDelta
dom 14/1210:40SYD - MDW
2 stops30h 07mDelta
Deal found 30/10$2,462
sab 29/1109:34MDW - SYD
2 stops29h 56mDelta
dom 7/1210:40SYD - MDW
2 stops22h 38mDelta
Deal found 28/10$2,537
ven 28/1110:47MDW - SYD
2 stops28h 43mDelta
ven 5/1210:40SYD - MDW
2 stops24h 38mDelta
Deal found 29/10$2,613
sab 29/1109:41MDW - SYD
2 stops29h 49mDelta
sab 13/1210:40SYD - MDW
2 stops24h 38mDelta
Deal found 30/10$2,615
mer 12/1113:47MDW - SYD
2 stops25h 43mDelta
dom 14/1210:40SYD - MDW
2 stops30h 07mDelta
Deal found 30/10$2,691
mer 24/1206:00MDW - SYD
2 stops33h 30mDelta
lun 12/114:15SYD - MDW
2 stops24h 54mDelta
Deal found 29/10$2,720

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 31 ottobre 2025.

Round-trip from

$1,731

One-way from

$1,156

Popular in

December

Cheapest in

August

Average price

$1,381
13/11-20/11
  • 13/11-20/11
  • 4 total stops
  • 68h 55m total
  • Chicago to Sydney
Search Deals
1/2
  • 1/2
  • 3 total stops
  • 33h 45m total
  • Chicago to Sydney
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($486 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($88 potential savings vs. average return price).
Search Deals
Average for round-trip flights in October 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 31 ottobre 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

ven 14/11

09:41-08:30

2 stops29h 49m

Sydney Kingsford Smith

sab 22/11

10:40-18:08

2 stops24h 28m

$2,085

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

lun 19/1

13:28-08:30

2 stops26h 02m

Sydney Kingsford Smith

lun 2/2

10:40-18:36

2 stops24h 56m

$2,232

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

gio 15/1

13:28-06:50

2 stops24h 22m

Sydney Kingsford Smith

mar 10/2

10:40-17:32

2 stops23h 52m

$2,308

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

sab 29/11

09:34-08:30

2 stops29h 56m

Sydney Kingsford Smith

dom 7/12

10:40-16:18

2 stops22h 38m

$2,537

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

mer 3/12

12:50-08:30

2 stops26h 40m

Sydney Kingsford Smith

sab 13/12

10:40-18:18

2 stops24h 38m

$2,537

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

gio 1/1

11:48-08:30

2 stops27h 42m

Sydney Kingsford Smith

sab 10/1

10:40-16:31

2 stops22h 51m

$2,567

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

ven 28/11

09:34-08:30

2 stops29h 56m

Sydney Kingsford Smith

ven 5/12

10:40-18:18

2 stops24h 38m

$2,613

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

gio 27/11

09:34-08:30

2 stops29h 56m

Sydney Kingsford Smith

gio 4/12

10:40-16:18

2 stops22h 38m

$2,613

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

sab 29/11

13:47-08:30

2 stops25h 43m

Sydney Kingsford Smith

sab 13/12

10:40-23:47

2 stops30h 07m

$2,613

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

dom 16/11

13:15-08:30

2 stops26h 15m

Sydney Kingsford Smith

dom 7/12

10:40-16:18

2 stops22h 38m

$2,689

Flights are sorted by cheapest return flights first.

Deals found on 30/10

Showing 1-10 of 21 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 29h 49m. 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
Manly
Terrigal
Randwick
Lithgow
Coogee
Leura
Bondi Beach
Cronulla

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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