$1,082+ 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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
13 Oct — 20 Oct1
1 adult
1 adult, Economy

Flights to Midway in 2025

Find the latest flights to Midway in 2025, 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 13 September 2025.

Return from

$1,309

One-way from

$1,082

Popular in

December

Cheapest in

February

Average price

$1,815
Air Canada
  • Air Canada
  • 1/11-15/11
  • 2 total stops
  • 45h 16m total
  • Sydney to Chicago
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10/12
  • 10/12
  • 3 total stops
  • 37h 47m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($678 potential increase over avg. return price).
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Cheapest flight prices on average. 4% potential price decrease ($112 potential savings vs. average return price).
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Average for return flights in September 2025
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Find flight deals to Midway Airport

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 13 September 2025.

Tue 30/909:25SYD - MDW
2 stops23h 10mDelta
Wed 12/1106:00MDW - SYD
2 stops33h 30mDelta
Deal found 11/9$1,500
Sun 26/1013:05SYD - MDW
1 stop26h 15mMultiple Airlines
Sun 2/1111:21MDW - SYD
1 stop26h 34mMultiple Airlines
Deal found 10/9$1,974
Sun 26/1010:25SYD - MDW
2 stops23h 18mDelta
Sun 2/1113:48MDW - SYD
2 stops25h 42mDelta
Deal found 11/9$2,226
Wed 8/1010:25SYD - MDW
2 stops24h 00mDelta
Tue 14/1013:08MDW - SYD
2 stops26h 27mDelta
Deal found 11/9$2,232
Mon 15/909:25SYD - MDW
2 stops24h 10mDelta
Wed 1/1013:08MDW - SYD
2 stops26h 27mDelta
Deal found 12/9$2,321
Fri 19/909:25SYD - MDW
2 stops27h 11mDelta
Fri 17/1009:35MDW - SYD
2 stops30h 00mDelta
Deal found 13/9$2,449
Sat 20/1210:40SYD - MDW
2 stops23h 39mDelta
Tue 30/1212:43MDW - SYD
2 stops26h 47mDelta
Deal found 12/9$2,478
Thu 18/909:25SYD - MDW
2 stops27h 11mDelta
Fri 17/1009:35MDW - SYD
2 stops30h 00mDelta
Deal found 12/9$2,517
Sat 11/1010:25SYD - MDW
2 stops24h 00mDelta
Sat 18/1011:10MDW - SYD
2 stops28h 25mDelta
Deal found 13/9$2,565
Mon 29/1210:40SYD - MDW
2 stops23h 39mDelta
Wed 28/106:00MDW - SYD
2 stops33h 30mDelta
Deal found 13/9$2,745

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 13 September 2025.
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

Tue 30/9

09:25-17:35

2 stops23h 10m

Chicago Midway

Wed 12/11

06:00-08:30

2 stops33h 30m

$1,500

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 28/10

09:40-18:25

2 stops24h 45m

Chicago Midway

Tue 4/11

10:40-08:30

2 stops28h 50m

$1,509

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 26/10

13:05-23:20

1 stop26h 15m

Chicago Midway

Sun 2/11

11:21-06:55

1 stop26h 34m

$1,974

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 26/10

10:25-17:43

2 stops23h 18m

Chicago Midway

Sun 2/11

13:48-08:30

2 stops25h 42m

$2,226

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 8/10

10:25-18:25

2 stops24h 00m

Chicago Midway

Tue 14/10

13:08-07:35

2 stops26h 27m

$2,232

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 21/12

10:40-16:15

2 stops22h 35m

Chicago Midway

Tue 30/12

09:54-06:50

2 stops27h 56m

$2,478

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 20/12

10:40-17:19

2 stops23h 39m

Chicago Midway

Tue 30/12

12:43-08:30

2 stops26h 47m

$2,478

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 11/10

10:25-18:25

2 stops24h 00m

Chicago Midway

Sat 18/10

11:10-07:35

2 stops28h 25m

$2,565

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 29/12

10:40-17:19

2 stops23h 39m

Chicago Midway

Wed 28/1

06:00-08:30

2 stops33h 30m

$2,745

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 10/12

17:45-14:32

3 stops37h 47m

$1,082

Flights are sorted by cheapest return flights first.

Deals found on 11/9

Showing 1-10 of 18 results
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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 35 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 (20 hours 47 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 Kitch is the closest property to Chicago Midway (0.0 km away from Chicago Midway).

See more FAQs

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

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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.

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