$1,304+ 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 30/7. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
13 Jun — 20 Jun1
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 14 May 2026.

Mon 7/909:15
SYD
-
MDW
2 stops24h 16m
Delta
Sat 19/914:00
MDW
-
SYD
2 stops25h 50m
Delta
Deal found 10/5$1,522
Tue 26/513:15
SYD
-
MDW
3 stops36h 54m
Multiple Airlines
Fri 29/506:00
MDW
-
SYD
3 stops38h 50m
Multiple Airlines
Deal found 12/5$1,571
Tue 2/613:15
SYD
-
MDW
3 stops36h 54m
Multiple Airlines
Fri 19/606:00
MDW
-
SYD
3 stops38h 50m
Multiple Airlines
Deal found 13/5$1,694
Fri 5/613:15
SYD
-
MDW
3 stops36h 49m
Multiple Airlines
Fri 19/606:00
MDW
-
SYD
3 stops49h 10m
Multiple Airlines
Deal found 13/5$1,763
Mon 27/709:15
SYD
-
MDW
2 stops38h 22m
Delta
Mon 21/913:05
MDW
-
SYD
2 stops26h 45m
Delta
Deal found 12/5$1,909
Wed 9/1210:40
SYD
-
MDW
2 stops23h 10m
Delta
Wed 13/112:30
MDW
-
SYD
2 stops27h 00m
Delta
Deal found 10/5$1,948
Thu 25/609:30
SYD
-
MDW
2 stops27h 41m
Multiple Airlines
Sat 11/706:00
MDW
-
SYD
2 stops34h 00m
Multiple Airlines
Deal found 12/5$2,343
Thu 21/509:15
SYD
-
MDW
2 stops23h 41m
Delta
Wed 3/612:53
MDW
-
SYD
2 stops26h 57m
Delta
Deal found 13/5$2,365

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 14 May 2026.

Return from

$1,425

One-way from

$1,304

Popular in

December

Cheapest in

August

Average price

$1,609
American Airlines
  • American Airlines
  • 8/9-21/9
  • 3 total stops
  • 46h 46m total
  • Sydney to Chicago
Search Deals
30/7
  • 30/7
  • 1 total stop
  • 41h 27m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($48 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($19 potential savings vs. average return price).
Search Deals
Average for return flights in May 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 14 May 2026.
Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest return flight
Fastest return journey

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 4/6

09:15-17:56

2 stops23h 41m

Chicago Midway

Wed 12/8

13:52-06:50

2 stops25h 58m

$2,365

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 1/10

09:15-21:46

2 stops27h 31m

Chicago Midway

Fri 9/10

12:30-07:50

2 stops27h 20m

$2,367

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 18/6

09:15-18:31

2 stops24h 16m

Chicago Midway

Tue 7/7

12:41-06:50

2 stops27h 09m

$2,372

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 8/6

09:15-18:18

2 stops24h 03m

Chicago Midway

Tue 7/7

13:18-06:50

2 stops26h 32m

$2,372

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 21/6

09:15-18:18

2 stops24h 03m

Chicago Midway

Sun 19/7

09:49-06:50

2 stops30h 01m

$2,435

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 3/6

09:15-18:33

2 stops24h 18m

Chicago Midway

Sat 13/6

13:49-06:50

2 stops26h 01m

$2,439

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 14/6

09:15-18:31

2 stops24h 16m

Chicago Midway

Mon 20/7

09:19-06:50

2 stops30h 31m

$2,439
Cheapest one-way

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 30/7

12:00-14:27

1 stop41h 27m

$1,304

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 15/7

09:15-22:15

2 stops28h 00m

$1,479

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 26/6

18:35-15:15

3 stops59h 40m

$1,504

Flights are sorted by cheapest return flights first.

Deals found on 14/5

Showing 1-10 of 15 resultsSorted by cheapest first
1
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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 41 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 25 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

Browse thousands of different options on Cheapflights for your next trip

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Search flights to Midway by cabin class

Find flights to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class flights to Chicago Midway Airport
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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights to Midway?

Cheapflights helps you search for flights to Midway via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

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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