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Cheap flights from Sydney to Chicago Midway Airport from $715

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 15/10. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
17 Oct — 24 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Sydney to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Sydney (SYD) to Midway (MDW). 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 17 September 2025.

Round-trip from

$1,429

One-way from

$715

Popular in

December

Cheapest in

March

Average price

$1,720
13/10-20/10
  • 13/10-20/10
  • 4 total stops
  • 78h 23m total
  • Sydney to Chicago
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15/10
  • 15/10
  • 3 total stops
  • 38h 45m total
  • Sydney to Chicago
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Highest demand for flights based on searches. 22% potential increase in price ($666 potential increase over avg. return price).
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Cheapest flight prices on average. 4% potential price decrease ($106 potential savings vs. average return price).
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Average for round-trip flights in September 2025
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Find flight deals from Sydney to Midway

Cheapest flights from Sydney to Midway
Explore the most affordable flight options available from Sydney to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 17 September 2025.

Mon 13/1010:10SYD - MDW
2 stops43h 28mMultiple Airlines
Mon 20/1005:10MDW - SYD
2 stops34h 55mMultiple Airlines
Deal found 15/9$1,429
Thu 30/1011:20SYD - MDW
2 stops41h 17mMultiple Airlines
Thu 6/1106:25MDW - SYD
2 stops32h 00mMultiple Airlines
Deal found 15/9$1,447
Tue 30/909:25SYD - MDW
2 stops24h 10mDelta
Wed 12/1113:14MDW - SYD
2 stops26h 16mDelta
Deal found 15/9$1,504
Fri 31/1011:20SYD - MDW
2 stops41h 17mMultiple Airlines
Fri 7/1106:30MDW - SYD
2 stops33h 30mMultiple Airlines
Deal found 16/9$1,519
Sat 1/1111:20SYD - MDW
2 stops41h 10mMultiple Airlines
Sat 15/1106:15MDW - SYD
2 stops33h 45mMultiple Airlines
Deal found 16/9$1,609
Thu 30/1009:40SYD - MDW
2 stops22h 29mDelta
Thu 6/1110:40MDW - SYD
2 stops28h 50mDelta
Deal found 14/9$2,009
Sat 8/1110:40SYD - MDW
2 stops24h 45mDelta
Sat 22/1109:32MDW - SYD
2 stops29h 58mDelta
Deal found 15/9$2,215
Thu 18/909:25SYD - MDW
2 stops27h 11mDelta
Fri 17/1009:35MDW - SYD
2 stops30h 00mDelta
Deal found 15/9$2,366
Fri 12/1214:05SYD - MDW
1 stop24h 23mMultiple Airlines
Fri 23/106:00MDW - SYD
2 stops32h 25mMultiple Airlines
Deal found 14/9$2,399

Cheapflights Fare Finder

 
Customise your flight search to find flights from Sydney to Midway 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 17 September 2025.
Use the filters below to find and compare flights from Sydney to Chicago Midway Airport that are best for you.

Fly from

Sydney

Fly to

Midway

Route

Depart

Return

Price

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 13/10

10:10-13:38

2 stops43h 28m

Chicago Midway

Mon 20/10

05:10-08:05

2 stops34h 55m

$1,429

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 30/9

09:25-18:35

2 stops24h 10m

Chicago Midway

Wed 12/11

13:14-08:30

2 stops26h 16m

$1,504

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 31/10

11:20-12:37

2 stops41h 17m

Chicago Midway

Fri 7/11

06:30-09:00

2 stops33h 30m

$1,519

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 1/11

11:20-12:30

2 stops41h 10m

Chicago Midway

Sat 15/11

06:15-09:00

2 stops33h 45m

$1,609

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 30/10

09:40-16:09

2 stops22h 29m

Chicago Midway

Thu 6/11

10:40-08:30

2 stops28h 50m

$2,009

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 8/11

10:40-18:25

2 stops24h 45m

Chicago Midway

Sat 22/11

09:41-08:30

2 stops29h 49m

$2,218

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 12/12

14:05-21:28

1 stop24h 23m

Chicago Midway

Fri 23/1

06:00-07:25

2 stops32h 25m

$2,399

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 14/10

10:25-17:43

2 stops23h 18m

Chicago Midway

Thu 23/10

12:48-07:35

2 stops26h 47m

$2,592

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 15/10

17:20-16:05

3 stops38h 45m

$715

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 17/10

17:20-11:44

3 stops58h 24m

$829

Flights are sorted by cheapest return flights first.

Deals found on 15/9

Showing 1-10 of 15 results
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2

Best time to book a flight from Sydney to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Sydney 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 Sydney to Midway. 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 from for flights from Sydney to Chicago Midway?

    For a flight from Sydney to Chicago Midway, you will be flying from Kingsford Smith. Sydney Kingsford Smith (SYD) is just 7.5 km from the centre of the city. Kingsford Smith is the only Sydney airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Sydney Kingsford Smith on a regular basis.

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

    A quick flight from Sydney to Chicago Midway Airport can take about 24h 10m. Delta provides one of the quickest options available for as low as $1,504. There are 14861 km between Sydney and Chicago Midway Airport.

  • Can I find deals for flights from Sydney to Midway that include hotel bookings?

    Yes. In addition to deals on Sydney to Midway flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Sydney to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sydney to Midway.

  • Can I find deals for business class flights from Sydney to Midway?

    Yes. Cheapflights offers flight deals from Sydney to Midway 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Sydney to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Sydney to O'Hare Intl flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Sydney to Midway?

When you search for this flight from Sydney to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Sydney to Midway?

Cheapflights helps you find that perfect flight to Midway from Sydney by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Sydney to Midway with no change fees?

Yes! Cheapflights helps users easily find flights from Sydney to Midway with no change fees.

Can Cheapflights notify me if prices for flights from Sydney to Midway become cheaper?

Of course! You can now track prices for flights from Sydney to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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