$1,045+ Cheap flights to Midway

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 27/4. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
23 Mar — 30 Mar1
1 adult
1 adult, Economy, 0 bags

Flights to Midway in 2026

Enter your travel dates to find the best prices.

Cheapest flights to Midway Airport
Explore the most affordable flight options available to Midway Airport. Find the lowest fares based on data from user searches, with prices last updated on 21 February 2026.

Tue 14/709:15
SYD
-
MDW
2 stops24h 16m
Delta
Tue 21/713:00
MDW
-
SYD
2 stops26h 50m
Delta
Deal found 18/2$1,506
Wed 4/310:40
SYD
-
MDW
2 stops23h 57m
Delta
Sun 15/313:10
MDW
-
SYD
2 stops24h 55m
Delta
Deal found 17/2$1,509
Fri 10/709:15
SYD
-
MDW
2 stops24h 16m
Delta
Sun 26/713:00
MDW
-
SYD
2 stops26h 50m
Delta
Deal found 18/2$1,555
Sat 7/310:40
SYD
-
MDW
2 stops28h 51m
Delta
Sat 14/319:20
MDW
-
SYD
2 stops42h 45m
Delta
Deal found 17/2$1,558
Thu 19/309:40
SYD
-
MDW
2 stops23h 42m
Delta
Tue 21/413:24
MDW
-
SYD
2 stops26h 26m
Delta
Deal found 21/2$1,724
Mon 1/609:15
SYD
-
MDW
2 stops23h 41m
Delta
Fri 31/714:00
MDW
-
SYD
2 stops25h 50m
Delta
Deal found 21/2$1,805
Sun 6/909:15
SYD
-
MDW
2 stops24h 16m
Delta
Sun 20/913:05
MDW
-
SYD
2 stops26h 45m
Delta
Deal found 17/2$2,012
Mon 23/210:40
SYD
-
MDW
2 stops23h 57m
Delta
Sun 8/313:10
MDW
-
SYD
2 stops26h 15m
Delta
Deal found 20/2$2,047
Mon 1/612:00
SYD
-
MDW
1 stop23h 06m
Multiple Airlines
Fri 31/721:11
MDW
-
SYD
2 stops47h 39m
Multiple Airlines
Deal found 18/2$2,223
Tue 7/409:15
SYD
-
MDW
2 stops23h 39m
Delta
Tue 14/410:41
MDW
-
SYD
2 stops29h 09m
Delta
Deal found 20/2$2,461

Find flight deals to Midway Airport

Find the latest flights to Midway in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 647,157 searches and data was last updated on 21 February 2026.

Return from

$1,354

One-way from

$1,045

Popular in

December

Cheapest in

April

Average price

$1,529
Air Canada
  • Air Canada
  • 10/3-25/3
  • 2 total stops
  • 45h 21m total
  • Sydney to Chicago
Search Deals
27/4
  • 27/4
  • 2 total stops
  • 42h 55m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($236 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($38 potential savings vs. average return price).
Search Deals
Average for return flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Locate flights to Midway that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 647,157 searches and data was last updated on 21 February 2026.
Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Fly from

Sydney

Route

Depart

Return

Price

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 19/3

13:15-22:31

2 stops25h 16m

Chicago Midway

Tue 21/4

14:12-06:50

2 stops25h 38m

$1,506

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 14/7

09:15-18:05

2 stops23h 50m

Chicago Midway

Wed 22/7

13:00-06:50

2 stops26h 50m

$1,506

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 15/7

09:15-18:05

2 stops23h 50m

Chicago Midway

Wed 22/7

13:00-06:50

2 stops26h 50m

$1,506

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 4/3

10:40-17:45

2 stops24h 05m

Chicago Midway

Sun 15/3

13:10-06:05

2 stops24h 55m

$1,506

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 5/3

10:40-17:45

2 stops24h 05m

Chicago Midway

Sun 15/3

13:10-06:05

2 stops24h 55m

$1,506

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 1/6

09:15-18:14

2 stops23h 59m

Chicago Midway

Fri 31/7

09:20-06:50

2 stops30h 30m

$1,555

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 10/7

09:15-18:31

2 stops24h 16m

Chicago Midway

Sun 26/7

13:00-06:50

2 stops26h 50m

$1,555

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 16/7

09:15-21:45

2 stops27h 30m

Chicago Midway

Thu 23/7

09:30-06:50

2 stops30h 20m

$1,555

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 7/3

10:40-22:31

2 stops28h 51m

Chicago Midway

Sat 14/3

19:20-06:05

2 stops42h 45m

$1,558

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 27/4

09:05-13:00

2 stops42h 55m

$1,045

Flights are sorted by cheapest return flights first.

Deals found on 20/2

Showing 1-10 of 17 results
1
2

Best time to book a flight to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway 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.

Cheapflights Insights

Everything you need to know about your flight to Chicago Midway Airport

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Midway ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Midway when rainfall is around 43.0 mm.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Midway, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

How long is the flight to Midway?

On average, a flight from Sydney to Midway takes 23 hours 39 minutes. Flights to Midway from other popular cities in Australia will vary in length. Below are a few examples of popular routes and their flight times.

FAQs about flying to Midway

  • Can I find cheaper flights to Midway if I am willing to have stopovers?

    Yes, flights with stopovers are often cheaper than direct flights. Keep an eye out for flight deals to Midway on Cheapflights that require 1 or 2 stops for potential cost savings.

  • Where does the fastest flight to Midway depart from?

    For those looking to save time traveling to Midway, Melbourne offers the quickest one-way flight (23 hours 31 minutes).

  • Does Chicago Midway have car hire?

    Yes. Those touching down at Chicago Midway can take advantage of the car hire services offered upon their arrival.

  • Are there hotels close to Chicago Midway?

    Yes. Chicago Midway has hotels nearby for those requiring accommodations. Midway Airport 2 Bedroom With Full Kitchen is the closest property to Chicago Midway (0.0 km away from Chicago Midway).

See more FAQs

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How does Cheapflights help users find flights to Midway?

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Why should you use Cheapflights to find cheap flight tickets to Midway?

Cheapflights simply makes it quick and affordable to book flights to Midway by bringing together all flight options from hundreds of airlines and agencies online — and we put them in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights to Midway with no change fees?

Certainly. Search results for flights to Midway shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights to Midway become cheaper?

Not ready to book yet? You can track prices for flights to Midway on Cheapflights with our Price Alerts feature and get notified when better prices are available.

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