HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$836+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Sydney to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 December 12, 2025.

This Delta deal was found by Cheapflights users on 12/10. 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 12/2610:40 amSYD - MDW
2 stops28h 42mDelta
Tue 1/61:28 pmMDW - SYD
2 stops24h 22mDelta
Deal found 12/10$1,724
This Delta deal was found by Cheapflights users on 12/10. 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 12/2810:40 amSYD - MDW
2 stops28h 42mDelta
Thu 1/811:21 amMDW - SYD
2 stops26h 29mDelta
Deal found 12/10$2,090
This Delta deal was found by Cheapflights users on 12/10. 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 12/1410:40 amSYD - MDW
2 stops22h 38mDelta
Fri 1/211:48 amMDW - SYD
2 stops27h 42mDelta
Deal found 12/10$2,196
This Delta deal was found by Cheapflights users on 12/11. 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.
Mon 12/1510:40 amSYD - MDW
2 stops30h 07mDelta
Thu 12/259:50 amMDW - SYD
2 stops28h 00mDelta
Deal found 12/11$2,249
This Delta deal was found by Cheapflights users on 12/11. 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.
Thu 12/252:15 pmSYD - MDW
2 stops25h 07mDelta
Thu 1/229:50 amMDW - SYD
2 stops29h 40mDelta
Deal found 12/11$2,515
This Korean Air deal was found by Cheapflights users on 12/10. 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 Korean Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/269:10 amSYD - MDW
2 stops30h 12mKorean Air
Thu 1/86:45 amMDW - SYD
2 stops31h 10mKorean Air
Deal found 12/10$13,087

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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$1,200
(Delta)

One-way from

$836
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$1,464
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. 19% potential increase in price ($242 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($45 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 12, 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

Tue 2/3

10:40 am-5:29 pm

2 stops23h 49m

Chicago Midway

Fri 2/20

1:49 pm-8:30 am

2 stops25h 41m

$1,200

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 2/2

10:40 am-5:55 pm

2 stops24h 15m

Chicago Midway

Thu 2/19

12:46 pm-6:50 am

2 stops25h 04m

$1,200

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 2/1

10:40 am-6:36 pm

2 stops24h 56m

Chicago Midway

Wed 2/18

1:28 pm-8:30 am

2 stops26h 02m

$1,200

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 5/28

9:25 am-6:05 pm

2 stops23h 40m

Chicago Midway

Sat 6/13

1:05 pm-6:35 am

2 stops26h 30m

$1,425

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 3/7

2:15 pm-10:42 pm

2 stops25h 27m

Chicago Midway

Sat 3/14

2:03 pm-7:25 am

2 stops25h 22m

$1,477

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 1/26

10:40 am-5:29 pm

2 stops23h 49m

Chicago Midway

Mon 2/2

12:48 pm-8:30 am

2 stops26h 42m

$1,577

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 1/24

2:15 pm-10:22 pm

2 stops25h 07m

Chicago Midway

Sat 1/31

1:26 pm-8:30 am

2 stops26h 04m

$1,674

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 12/27

10:40 am-5:19 pm

2 stops23h 39m

Chicago Midway

Wed 1/7

11:21 am-8:30 am

2 stops28h 09m

$1,724

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 12/26

10:40 am-10:22 pm

2 stops28h 42m

Chicago Midway

Tue 1/6

1:28 pm-6:50 am

2 stops24h 22m

$1,724

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 1/25

10:40 am-6:36 pm

2 stops24h 56m

Chicago Midway

Fri 1/30

10:48 am-8:30 am

2 stops28h 42m

$1,774

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 24 results
1
2
3

Compare providers for flights from Sydney to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Sydney to Midway in December.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Sydney-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Sydney-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 23h 49m. 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.