$719+ 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 20/10. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
5 Sep — 12 Sep1
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 6 August 2026.

Tue 8/909:15 -
2 stops24h 04m
Tue 22/914:00 -
2 stops25h 50m
Deal found 1/8$2,167
Sat 29/809:15 -
2 stops23h 46m
Sat 5/910:56 -
2 stops28h 54m
Deal found 1/8$2,316
Fri 18/912:00 -
1 stop38h 59m
Fri 25/912:54 -
1 stop27h 01m
Deal found 4/8$2,357
Thu 24/909:15 -
2 stops28h 29m
Thu 15/1013:27 -
2 stops26h 23m
Deal found 2/8$2,528
Thu 1/1009:15 -
2 stops24h 04m
Fri 9/1009:29 -
2 stops30h 21m
Deal found 3/8$2,730
Tue 8/909:15 -
2 stops24h 04m
Fri 18/913:19 -
2 stops26h 31m
Deal found 5/8$2,798
Sat 19/909:15 -
2 stops28h 29m
Sun 27/909:29 -
2 stops30h 21m
Deal found 5/8$2,884

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 6 August 2026.

Return from

$1,195

One-way from

$710

Popular in

July

Cheapest in

August

Average price

$1,532
8/9-22/9
  • 8/9-22/9
  • 5 total stops
  • 88h 07m total
  • Sydney to Chicago
Search Deals
18/11
  • 18/11
  • 3 total stops
  • 37h 58m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($49 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($25 potential savings vs. average return price).
Search Deals
Average for return flights in August 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 6 August 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 Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 8/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Tue 22/9

14:00-06:50

2 stops25h 50m

$2,167

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 24/9

09:15-22:44

2 stops28h 29m

Chicago Midway

Thu 15/10

13:27-07:50

2 stops26h 23m

$2,528

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 1/10

09:15-18:19

2 stops24h 04m

Chicago Midway

Fri 9/10

09:29-07:50

2 stops30h 21m

$2,730

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 8/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Fri 18/9

13:19-06:50

2 stops26h 31m

$2,798

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 19/9

09:15-22:44

2 stops28h 29m

Chicago Midway

Sun 27/9

09:29-06:50

2 stops30h 21m

$2,884

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 26/9

09:15-17:59

2 stops23h 44m

Chicago Midway

Tue 6/10

13:27-07:50

2 stops26h 23m

$7,399

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 24/9

09:15-22:44

2 stops28h 29m

Chicago Midway

Sun 4/10

09:59-07:50

2 stops29h 51m

$7,635

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 25/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Mon 5/10

13:00-07:50

2 stops26h 50m

$7,985
Cheapest one-way

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sun 25/10

14:00-10:58

3 stops36h 58m

$840

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 5/9

07:40-20:31

2 stops51h 51m

$1,264

Flights are sorted by cheapest return flights first.

Deals found on 3/8

Showing 1-10 of 15 resultsSorted by cheapest first
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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 28 hours 29 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 4 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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