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Cheap flights from Sydney to Chicago Midway Airport from $1,175

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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
28 Nov — 5 Dec1
1 adult
1 adult, Economy, 0 bags

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 29 October 2025.

Round-trip from

$2,142

One-way from

$1,175

Popular in

December

Cheapest in

March

Average price

$1,710
Delta
  • Delta
  • 25/12-24/1
  • 4 total stops
  • 51h 24m total
  • Sydney to Chicago
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3/11
  • 3/11
  • 2 total stops
  • 52h 40m total
  • Sydney to Chicago
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Highest demand for flights based on searches. 21% potential increase in price ($648 potential increase over avg. return price).
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Cheapest flight prices on average. 4% potential price decrease ($107 potential savings vs. average return price).
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Average for round-trip flights in October 2025
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Find flight deals from Sydney to Midway

Enter your travel dates to find the best prices.

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 29 October 2025.

Thu 25/1210:40SYD - MDW
2 stops28h 42mDelta
Sat 24/110:46MDW - SYD
2 stops27h 04mDelta
Deal found 27/10$2,282
Sun 23/1110:40SYD - MDW
2 stops24h 38mDelta
Sun 30/1109:41MDW - SYD
2 stops29h 49mDelta
Deal found 25/10$2,427
Tue 25/1110:40SYD - MDW
2 stops24h 38mDelta
Thu 29/113:28MDW - SYD
2 stops24h 22mDelta
Deal found 26/10$2,430
Tue 25/1114:05SYD - MDW
1 stop27h 08mMultiple Airlines
Thu 29/106:00MDW - SYD
2 stops32h 25mMultiple Airlines
Deal found 26/10$2,456
Mon 3/1110:40SYD - MDW
2 stops22h 34mDelta
Mon 17/1110:47MDW - SYD
2 stops28h 43mDelta
Deal found 26/10$2,505
Thu 30/1009:40SYD - MDW
2 stops22h 29mDelta
Thu 26/309:30MDW - SYD
2 stops28h 35mDelta
Deal found 27/10$2,579
Sat 1/1109:40SYD - MDW
2 stops24h 15mDelta
Sat 8/1109:20MDW - SYD
2 stops30h 10mDelta
Deal found 26/10$2,654
Thu 11/1210:40SYD - MDW
2 stops30h 07mDelta
Thu 18/1213:14MDW - SYD
2 stops26h 16mDelta
Deal found 27/10$2,731
Wed 17/1210:40SYD - MDW
2 stops22h 54mDelta
Sun 4/111:48MDW - SYD
2 stops26h 02mDelta
Deal found 28/10$2,852
Mon 3/1114:05SYD - MDW
1 stop20h 44mMultiple Airlines
Mon 17/1112:30MDW - SYD
2 stops25h 25mMultiple Airlines
Deal found 26/10$3,133
Thu 18/1210:40SYD - MDW
2 stops30h 07mDelta
Mon 29/1212:45MDW - SYD
2 stops26h 45mDelta
Deal found 26/10$3,548

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 29 October 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

Thu 25/12

10:40-17:19

2 stops23h 39m

Chicago Midway

Sat 24/1

11:45-08:30

2 stops27h 45m

$2,142

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 17/1

14:15-22:09

2 stops24h 54m

Chicago Midway

Sat 24/1

11:45-06:50

2 stops26h 05m

$2,217

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 20/1

10:40-17:55

2 stops24h 15m

Chicago Midway

Sun 25/1

13:28-06:50

2 stops24h 22m

$2,517

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 23/11

10:40-18:08

2 stops24h 28m

Chicago Midway

Sun 30/11

10:47-08:30

2 stops28h 43m

$2,579

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 27/1

14:15-22:26

2 stops25h 11m

Chicago Midway

Sat 31/1

13:28-08:30

2 stops26h 02m

$2,591

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 13/1

10:40-22:09

2 stops28h 29m

Chicago Midway

Sat 17/1

13:28-06:50

2 stops24h 22m

$2,591

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 17/12

10:40-16:34

2 stops22h 54m

Chicago Midway

Sun 4/1

11:48-06:50

2 stops26h 02m

$2,852

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 17/1

14:05-13:07

1 stop40h 02m

Chicago Midway

Sat 24/1

06:00-06:55

2 stops31h 55m

$2,867

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 14/12

10:40-23:47

2 stops30h 07m

Chicago Midway

Fri 2/1

09:50-08:30

2 stops29h 40m

$3,857

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 25/12

14:15-22:22

2 stops25h 07m

Chicago Midway

Mon 12/1

09:50-08:30

2 stops29h 40m

$3,872

Flights are sorted by cheapest return flights first.

Deals found on 26/10

Showing 1-10 of 17 results
1
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 23h 39m. Delta provides one of the quickest options available for as low as $2,142. 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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