$756+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
22 Aug — 29 Aug1
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 23 July 2026.

Wed 9/913:15
SYD
-
MDW
3 stops36h 43m
Multiple Airlines
Sun 13/907:25
MDW
-
SYD
3 stops37h 25m
Multiple Airlines
Deal found 20/7$1,318
Thu 6/813:15
SYD
-
MDW
3 stops35h 36m
Multiple Airlines
Wed 19/806:05
MDW
-
SYD
3 stops38h 45m
Multiple Airlines
Deal found 20/7$1,476
Thu 6/809:10
SYD
-
MDW
2 stops26h 22m
Multiple Airlines
Sun 23/806:05
MDW
-
SYD
2 stops34h 00m
Multiple Airlines
Deal found 21/7$2,027
Tue 4/812:00
SYD
-
MDW
1 stop19h 51m
Multiple Airlines
Tue 11/817:46
MDW
-
SYD
2 stops27h 04m
Multiple Airlines
Deal found 19/7$2,351
Mon 14/909:15
SYD
-
MDW
2 stops24h 04m
Delta
Tue 6/1013:00
MDW
-
SYD
2 stops26h 50m
Delta
Deal found 18/7$2,441
Thu 10/909:15
SYD
-
MDW
2 stops24h 04m
Delta
Wed 23/913:00
MDW
-
SYD
2 stops26h 50m
Delta
Deal found 20/7$2,442
Thu 1/1009:15
SYD
-
MDW
2 stops24h 04m
Delta
Fri 9/1009:59
MDW
-
SYD
2 stops29h 51m
Delta
Deal found 20/7$2,517
Sun 1/1110:40
SYD
-
MDW
2 stops24h 25m
Delta
Sun 8/1112:28
MDW
-
SYD
2 stops27h 02m
Delta
Deal found 22/7$2,555
Sat 26/1210:40
SYD
-
MDW
2 stops23h 10m
Delta
Tue 12/113:00
MDW
-
SYD
2 stops24h 50m
Delta
Deal found 18/7$2,644
Wed 9/909:15
SYD
-
MDW
2 stops24h 04m
Delta
Sun 13/913:19
MDW
-
SYD
2 stops26h 31m
Delta
Deal found 20/7$2,747

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 23 July 2026.

Return from

$1,318

One-way from

$756

Popular in

May

Cheapest in

October

Average price

$1,895
9/9-13/9
  • 9/9-13/9
  • 6 total stops
  • 74h 08m total
  • Sydney to Chicago
Search Deals
7/9
  • 7/9
  • 3 total stops
  • 36h 40m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($145 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 23 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

Wed 9/9

13:15-10:58

3 stops36h 43m

Chicago Midway

Sun 13/9

07:25-11:50

3 stops37h 25m

$1,318

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 6/8

13:15-09:51

3 stops35h 36m

Chicago Midway

Wed 19/8

06:05-11:50

3 stops38h 45m

$1,476

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 14/10

10:15-18:05

2 stops23h 50m

Chicago Midway

Wed 21/10

13:00-07:50

2 stops26h 50m

$2,442

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 10/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Wed 23/9

13:00-06:50

2 stops26h 50m

$2,442
Fastest return journey

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 18/11

10:40-16:50

2 stops23h 10m

Chicago Midway

Wed 25/11

13:00-08:30

2 stops26h 30m

$2,442

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 1/10

09:15-18:19

2 stops24h 04m

Chicago Midway

Fri 9/10

09:59-07:50

2 stops29h 51m

$2,517

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 1/11

10:40-19:05

2 stops24h 25m

Chicago Midway

Sun 8/11

12:28-08:30

2 stops27h 02m

$2,555

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 27/12

10:40-22:10

2 stops28h 30m

Chicago Midway

Wed 13/1

13:00-08:30

2 stops26h 30m

$2,644

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 9/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Sun 13/9

13:19-06:50

2 stops26h 31m

$2,747

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

$2,820

Flights are sorted by cheapest return flights first.

Deals found on 20/7

Showing 1-10 of 16 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 23 hours 10 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 $155, while return flights cost around $450.

  • How much is a return flight to Midway?

    A return flight to Midway will typically cost around $470, however they can be found for as little as $450.

  • 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 5 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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Search flights to Midway by cabin class

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Fly with Cheapflights

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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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