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Midway

$625+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
mar. 13 — mar. 201
vie. 3/13
vie. 3/20
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 febrero 11, 2026.

This Delta deal was found by Cheapflights users on 2/9. 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.
mar. 10/610:15 am
SYD
-
MDW
2 stops27h 30m
Delta
lun. 10/121:00 pm
MDW
-
SYD
2 stops26h 50m
Delta
Deal found 2/9$1,097
This Delta deal was found by Cheapflights users on 2/7. 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.
vie. 3/279:40 am
SYD
-
MDW
2 stops25h 00m
Delta
sáb. 4/41:10 pm
MDW
-
SYD
2 stops26h 40m
Delta
Deal found 2/7$1,196
This Delta deal was found by Cheapflights users on 2/9. 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.
mié. 10/710:15 am
SYD
-
MDW
2 stops24h 22m
Delta
mar. 10/131:05 pm
MDW
-
SYD
2 stops26h 45m
Delta
Deal found 2/9$1,217
This Delta deal was found by Cheapflights users on 2/11. 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.
jue. 3/199:40 am
SYD
-
MDW
2 stops25h 00m
Delta
mar. 4/212:12 pm
MDW
-
SYD
2 stops25h 38m
Delta
Deal found 2/11$1,220
This Delta deal was found by Cheapflights users on 2/11. 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.
sáb. 3/149:40 am
SYD
-
MDW
2 stops28h 51m
Delta
sáb. 3/286:00 am
MDW
-
SYD
2 stops33h 50m
Delta
Deal found 2/11$1,326
This Delta deal was found by Cheapflights users on 2/7. 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.
vie. 7/109:15 am
SYD
-
MDW
2 stops24h 16m
Delta
dom. 7/262:00 pm
MDW
-
SYD
2 stops25h 50m
Delta
Deal found 2/7$1,353
This Delta deal was found by Cheapflights users on 2/8. 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.
lun. 6/159:15 am
SYD
-
MDW
2 stops24h 16m
Delta
sáb. 8/151:00 pm
MDW
-
SYD
2 stops26h 50m
Delta
Deal found 2/8$1,405
This Delta deal was found by Cheapflights users on 2/8. 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.
vie. 9/259:15 am
SYD
-
MDW
2 stops24h 16m
Delta
sáb. 10/31:00 pm
MDW
-
SYD
2 stops26h 50m
Delta
Deal found 2/8$1,412
This Delta deal was found by Cheapflights users on 2/9. 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.
mar. 6/29:15 am
SYD
-
MDW
2 stops23h 41m
Delta
mar. 8/41:05 pm
MDW
-
SYD
2 stops26h 45m
Delta
Deal found 2/9$1,451
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/52:00 pm
SYD
-
MDW
2 stops24h 12m
Multiple Airlines
mié. 3/1811:25 am
MDW
-
SYD
1 stop27h 30m
Multiple Airlines
Deal found 2/9$1,461

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 febrero 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$1,097
(Delta)

One-way from

$625
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$1,079
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. 14% potential increase in price ($172 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 febrero 11, 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

jue. 3/5

10:40 am-5:45 pm

2 stops24h 05m

Chicago Midway

mié. 3/18

12:47 pm-7:25 am

2 stops26h 38m

$1,097

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

jue. 3/19

1:15 pm-10:31 pm

2 stops25h 16m

Chicago Midway

mar. 4/21

1:23 pm-6:50 am

2 stops26h 27m

$1,097

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

mar. 3/10

1:15 pm-10:31 pm

2 stops25h 16m

Chicago Midway

mar. 3/17

1:10 pm-6:05 am

2 stops24h 55m

$1,097

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

vie. 3/27

9:40 am-6:40 pm

2 stops25h 00m

Chicago Midway

sáb. 4/4

1:10 pm-6:50 am

2 stops26h 40m

$1,196

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

mié. 3/25

9:40 am-10:31 pm

2 stops28h 51m

Chicago Midway

mié. 4/1

9:30 am-7:50 am

2 stops30h 20m

$1,217

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

vie. 7/10

9:15 am-6:31 pm

2 stops24h 16m

Chicago Midway

dom. 7/26

2:00 pm-6:50 am

2 stops25h 50m

$1,353

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

lun. 6/15

9:15 am-6:31 pm

2 stops24h 16m

Chicago Midway

sáb. 8/15

1:00 pm-6:50 am

2 stops26h 50m

$1,405

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

mar. 6/2

9:15 am-5:56 pm

2 stops23h 41m

Chicago Midway

mar. 8/4

1:05 pm-6:50 am

2 stops26h 45m

$1,451

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

mié. 6/3

9:15 am-5:56 pm

2 stops23h 41m

Chicago Midway

mar. 8/4

2:00 pm-6:50 am

2 stops25h 50m

$1,462

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

mar. 2/24

2:00 pm-7:07 pm

3 stops46h 07m

$627

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

Showing 1-10 of 21 results
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  • 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 24h 05m. 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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