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Midway

$658+ Cheap flights from Sydney (SYD) to Midway (MDW)

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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap 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 January 27, 2026.

This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/110:40 am
SYD
-
MDW
2 stops24h 15m
Delta
Sun 2/1511:45 am
MDW
-
SYD
2 stops26h 05m
Delta
Deal found 1/26$1,245
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/1610:40 am
SYD
-
MDW
2 stops25h 00m
Delta
Wed 3/49:34 am
MDW
-
SYD
2 stops29h 56m
Delta
Deal found 1/26$1,388
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/49:15 am
SYD
-
MDW
2 stops24h 16m
Delta
Tue 8/112:00 pm
MDW
-
SYD
2 stops25h 50m
Delta
Deal found 1/26$1,428
This Delta deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/269:15 am
SYD
-
MDW
2 stops38h 23m
Delta
Sat 7/186:45 pm
MDW
-
SYD
2 stops45h 05m
Delta
Deal found 1/27$1,484
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/129:15 am
SYD
-
MDW
2 stops24h 16m
Delta
Sun 7/121:00 pm
MDW
-
SYD
2 stops26h 50m
Delta
Deal found 1/26$1,583
This Delta deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/289:15 am
SYD
-
MDW
2 stops47h 50m
Delta
Sat 7/186:45 pm
MDW
-
SYD
2 stops45h 05m
Delta
Deal found 1/27$1,588
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/109:40 am
SYD
-
MDW
2 stops23h 42m
Delta
Tue 3/171:10 pm
MDW
-
SYD
2 stops26h 20m
Delta
Deal found 1/26$1,635
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/119:40 am
SYD
-
MDW
2 stops24h 14m
Delta
Wed 3/181:10 pm
MDW
-
SYD
2 stops26h 15m
Delta
Deal found 1/25$1,636
This Delta deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2410:40 am
SYD
-
MDW
2 stops25h 00m
Delta
Tue 3/31:29 pm
MDW
-
SYD
2 stops24h 21m
Delta
Deal found 1/27$1,640
This Delta deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:15 am
SYD
-
MDW
2 stops23h 50m
Delta
Sun 7/262:00 pm
MDW
-
SYD
2 stops25h 50m
Delta
Deal found 1/24$1,654

Find 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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$1,388
(Delta)

One-way from

$658
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$1,007
Provider with most accurate pricing for Sydney Kingsford Smith-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Sydney Kingsford Smith-Chicago Midway flights.
Search Deals
From Sydney Kingsford Smith to Chicago Midway
Search Deals
One-way flight from Sydney Kingsford Smith to Chicago Midway
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($195 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize 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 2,558,603 searches. Data last updated January 27, 2026.
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 2/16

10:40 am-6:40 pm

2 stops25h 00m

Chicago Midway

Wed 3/4

9:34 am-8:30 am

2 stops29h 56m

$1,388

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 6/26

9:15 am-8:38 am

2 stops38h 23m

Chicago Midway

Wed 7/15

1:00 pm-6:50 am

2 stops26h 50m

$1,484

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 6/26

9:15 am-8:38 am

2 stops38h 23m

Chicago Midway

Tue 7/14

1:00 pm-6:50 am

2 stops26h 50m

$1,484

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 6/26

9:15 am-9:51 am

2 stops39h 36m

Chicago Midway

Mon 7/13

1:00 pm-6:50 am

2 stops26h 50m

$1,484

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 6/12

9:15 am-6:31 pm

2 stops24h 16m

Chicago Midway

Sun 7/12

1:00 pm-6:50 am

2 stops26h 50m

$1,583

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 3/10

9:40 am-5:22 pm

2 stops23h 42m

Chicago Midway

Tue 3/17

1:10 pm-7:30 am

2 stops26h 20m

$1,635

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 3/11

9:40 am-5:54 pm

2 stops24h 14m

Chicago Midway

Wed 3/18

1:10 pm-7:25 am

2 stops26h 15m

$1,636

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 2/24

10:40 am-6:40 pm

2 stops25h 00m

Chicago Midway

Tue 3/3

1:29 pm-6:50 am

2 stops24h 21m

$1,640

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 7/10

9:15 am-6:05 pm

2 stops23h 50m

Chicago Midway

Sun 7/26

2:00 pm-6:50 am

2 stops25h 50m

$1,654

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 3/17

8:10 am-10:25 am

3 stops42h 15m

$658

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 18 results
1
2
  • Most accurate provider: When it comes to deals on Sydney-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Sydney-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Sydney-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Sydney-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Sydney-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 round-trip 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?

    Sydney Kingsford Smith (SYD) is the airport you will fly out of if you book a flight from Sydney to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Kingsford Smith; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Sydney airport to Chicago Midway. It is only a 4.6 mi journey to Kingsford Smith (SYD) from Sydney’s city center.

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

    Departing from Sydney to Chicago Midway Airport will take you 25h. The distance between Sydney and Chicago Midway Airport is about 9234 mi.

  • 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 vacation 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Sydney to Midway

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