$702+ 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 25/8. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
29 Aug — 5 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 30 July 2026.

Thu 10/917:50
SYD
-
MDW
2 stops33h 09m
Multiple Airlines
Thu 17/906:25
MDW
-
SYD
2 stops34h 05m
Multiple Airlines
Deal found 27/7$2,081
Mon 24/812:00
SYD
-
MDW
1 stop23h 31m
Multiple Airlines
Sun 13/912:54
MDW
-
SYD
1 stop27h 01m
Multiple Airlines
Deal found 29/7$2,164
Wed 9/1210:40
SYD
-
MDW
2 stops22h 59m
Delta
Thu 14/110:35
MDW
-
SYD
2 stops28h 55m
Delta
Deal found 26/7$2,498
Tue 24/1110:40
SYD
-
MDW
2 stops22h 59m
Delta
Mon 30/1112:30
MDW
-
SYD
2 stops27h 00m
Delta
Deal found 28/7$2,530
Thu 8/1010:15
SYD
-
MDW
2 stops23h 45m
Delta
Thu 15/1009:29
MDW
-
SYD
2 stops30h 21m
Delta
Deal found 27/7$2,535
Fri 25/909:15
SYD
-
MDW
2 stops24h 04m
Delta
Fri 2/1013:19
MDW
-
SYD
2 stops26h 31m
Delta
Deal found 29/7$2,607
Tue 8/1210:40
SYD
-
MDW
2 stops29h 16m
Delta
Fri 22/113:00
MDW
-
SYD
2 stops26h 30m
Delta
Deal found 25/7$2,663
Sun 27/909:15
SYD
-
MDW
2 stops24h 04m
Delta
Sat 3/1011:35
MDW
-
SYD
2 stops28h 15m
Delta
Deal found 28/7$2,698
Tue 8/909:15
SYD
-
MDW
2 stops24h 04m
Delta
Tue 22/913:19
MDW
-
SYD
2 stops26h 31m
Delta
Deal found 29/7$2,747
Wed 26/809:15
SYD
-
MDW
2 stops23h 46m
Delta
Wed 16/913:00
MDW
-
SYD
2 stops26h 50m
Delta
Deal found 29/7$2,757
Tue 8/909:15
SYD
-
MDW
2 stops24h 04m
Delta
Tue 15/914:00
MDW
-
SYD
2 stops25h 50m
Delta
Deal found 26/7$2,761

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 30 July 2026.

Return from

$1,213

One-way from

$702

Popular in

May

Cheapest in

October

Average price

$1,945
8/9-14/9
  • 8/9-14/9
  • 5 total stops
  • 70h 22m total
  • Sydney to Chicago
Search Deals
25/8
  • 25/8
  • 3 total stops
  • 36h 40m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($147 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($24 potential savings vs. average return price).
Search Deals
Average for return flights in July 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 30 July 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

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 24/8

12:00-20:31

1 stop23h 31m

Chicago Midway

Sun 13/9

12:54-06:55

1 stop27h 01m

$2,164

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 9/12

10:40-16:39

2 stops22h 59m

Chicago Midway

Thu 14/1

10:35-08:30

2 stops28h 55m

$2,498

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 24/11

10:40-16:39

2 stops22h 59m

Chicago Midway

Mon 30/11

12:30-08:30

2 stops27h 00m

$2,530

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 8/10

10:15-18:00

2 stops23h 45m

Chicago Midway

Thu 15/10

09:29-07:50

2 stops30h 21m

$2,535

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 8/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Tue 22/9

13:19-06:50

2 stops26h 31m

$2,747

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 3/9

09:15-18:01

2 stops23h 46m

Chicago Midway

Wed 16/9

13:00-06:50

2 stops26h 50m

$2,761
Fastest return journey

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 8/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Tue 15/9

14:00-06:50

2 stops25h 50m

$2,761

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 9/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Wed 16/9

13:00-06:50

2 stops26h 50m

$2,766

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 17/8

12:00-17:22

1 stop20h 22m

Chicago Midway

Mon 31/8

21:26-06:25

2 stops41h 59m

$2,806

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 10/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Thu 17/9

13:19-06:50

2 stops26h 31m

$2,815

Flights are sorted by cheapest return flights first.

Deals found on 27/7

Showing 1-10 of 18 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 22 hours 59 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.

  • What is the cheapest airport to fly to in Midway?

    Chicago Midway is currently the cheapest airport to fly to in Midway. One-way flights to Chicago Midway typically cost $156, while return flights cost around $453.

  • How much is a return flight to Midway?

    A return flight to Midway will typically cost around $473, however they can be found for as little as $453.

  • Where does the fastest flight to Midway depart from?

    For those looking to save time traveling to Midway, Sydney Kingsford Smith offers the quickest one-way flight (22 hours 59 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

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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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