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Cheap flights from Sydney to Chicago Midway Airport from $1,022

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.
SYD — MDW
1 Sep — 8 Sep1
1 adult

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 27 August 2025.

Round-trip from

$1,779

One-way from

$1,022

Popular in

December

Cheapest in

February

Average price

$1,606
10/10-17/10
  • 10/10-17/10
  • 4 total stops
  • 80h 54m total
  • Sydney to Chicago
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1/9
  • 1/9
  • 3 total stops
  • 29h 04m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($713 potential increase over avg. return price).
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Cheapest flight prices on average. 4% potential price decrease ($118 potential savings vs. average return price).
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Average for round-trip flights in August 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 27 August 2025.

Fri 10/1010:10SYD - MDW
2 stops45h 59mMultiple Airlines
Fri 17/1005:10MDW - SYD
2 stops34h 55mMultiple Airlines
Deal found 26/8$1,779
Thu 27/1110:40SYD - MDW
2 stops22h 59mDelta
Mon 8/1209:30MDW - SYD
2 stops30h 00mDelta
Deal found 26/8$2,075
Mon 3/1110:40SYD - MDW
2 stops28h 34mDelta
Wed 19/1109:41MDW - SYD
2 stops29h 49mDelta
Deal found 25/8$2,076
Mon 24/1110:40SYD - MDW
2 stops24h 38mDelta
Wed 31/1209:30MDW - SYD
2 stops30h 00mDelta
Deal found 25/8$2,078
Sat 1/1109:40SYD - MDW
2 stops24h 15mDelta
Mon 17/1110:47MDW - SYD
2 stops28h 43mDelta
Deal found 25/8$2,152
Tue 30/909:25SYD - MDW
2 stops24h 10mDelta
Wed 12/1112:47MDW - SYD
2 stops26h 43mDelta
Deal found 26/8$2,375
Mon 1/909:25SYD - MDW
2 stops23h 12mDelta
Tue 9/910:31MDW - SYD
2 stops29h 04mDelta
Deal found 26/8$2,525
Wed 3/909:25SYD - MDW
2 stops24h 12mDelta
Tue 16/912:43MDW - SYD
2 stops26h 52mDelta
Deal found 24/8$2,528
Mon 22/909:25SYD - MDW
2 stops24h 10mDelta
Mon 29/913:43MDW - SYD
2 stops25h 52mDelta
Deal found 24/8$2,643
Sat 20/1210:40SYD - MDW
2 stops22h 37mDelta
Wed 31/1206:00MDW - SYD
2 stops33h 30mDelta
Deal found 24/8$2,790
Mon 22/909:25SYD - MDW
2 stops23h 10mDelta
Sat 27/911:00MDW - SYD
2 stops28h 35mDelta
Deal found 25/8$2,868
Sun 14/1210:40SYD - MDW
2 stops24h 27mDelta
Tue 6/110:35MDW - SYD
2 stops28h 55mDelta
Deal found 24/8$2,941

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 27 August 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

Fri 10/10

10:10-16:09

2 stops45h 59m

Chicago Midway

Fri 17/10

05:10-08:05

2 stops34h 55m

$1,779

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 27/11

10:40-16:39

2 stops22h 59m

Chicago Midway

Mon 8/12

09:30-08:30

2 stops30h 00m

$2,075

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/11

10:40-22:14

2 stops28h 34m

Chicago Midway

Wed 19/11

09:41-08:30

2 stops29h 49m

$2,076

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 24/11

10:40-18:18

2 stops24h 38m

Chicago Midway

Wed 31/12

09:30-08:30

2 stops30h 00m

$2,078

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 1/11

09:40-17:55

2 stops24h 15m

Chicago Midway

Mon 17/11

10:47-08:30

2 stops28h 43m

$2,152

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 2/11

10:40-19:25

2 stops24h 45m

Chicago Midway

Tue 18/11

13:47-08:30

2 stops25h 43m

$2,152

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 30/9

09:25-18:35

2 stops24h 10m

Chicago Midway

Wed 12/11

12:47-08:30

2 stops26h 43m

$2,375

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 19/11

10:40-18:18

2 stops24h 38m

Chicago Midway

Mon 24/11

13:47-08:30

2 stops25h 43m

$2,528

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 22/9

09:25-18:35

2 stops24h 10m

Chicago Midway

Mon 29/9

13:43-06:35

2 stops25h 52m

$2,643

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 20/12

10:40-16:17

2 stops22h 37m

Chicago Midway

Wed 31/12

06:00-08:30

2 stops33h 30m

$2,790

Flights are sorted by cheapest return flights first.

Deals found on 26/8

Showing 1-10 of 24 results
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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 22h 59m. Delta provides one of the quickest options available for as low as $2,075. 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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