$1,149+ 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 16/11. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
16 Nov — 23 Nov1
1 adult
1 adult, Economy

Find flight deals to Midway Airport

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 17 October 2025.

Sat 1/1111:20SYD - MDW
2 stops41h 10mMultiple Airlines
Sun 16/1106:30MDW - SYD
2 stops33h 30mMultiple Airlines
Deal found 15/10$1,729
Fri 26/1210:40SYD - MDW
2 stops22h 44mDelta
Tue 3/214:00MDW - SYD
2 stops25h 30mDelta
Deal found 15/10$2,145
Wed 24/1210:40SYD - MDW
2 stops28h 42mDelta
Wed 4/209:30MDW - SYD
2 stops30h 00mDelta
Deal found 15/10$2,219
Wed 12/1110:40SYD - MDW
2 stops24h 38mDelta
Wed 19/1113:47MDW - SYD
2 stops25h 43mDelta
Deal found 15/10$2,368
Wed 24/1210:40SYD - MDW
2 stops28h 42mDelta
Thu 22/113:00MDW - SYD
2 stops24h 50mDelta
Deal found 15/10$2,445
Sun 16/1110:40SYD - MDW
2 stops22h 58mDelta
Sun 30/1109:41MDW - SYD
2 stops29h 49mDelta
Deal found 16/10$2,456
Mon 27/1009:40SYD - MDW
2 stops24h 03mDelta
Sun 9/1113:47MDW - SYD
2 stops25h 43mDelta
Deal found 16/10$2,531
Sat 1/1109:40SYD - MDW
2 stops24h 15mDelta
Wed 19/1109:34MDW - SYD
2 stops29h 56mDelta
Deal found 15/10$2,593
Mon 27/1013:05SYD - MDW
1 stop26h 15mMultiple Airlines
Sun 9/1112:30MDW - SYD
2 stops49h 55mMultiple Airlines
Deal found 16/10$2,596
Thu 25/1214:15SYD - MDW
2 stops25h 07mDelta
Thu 5/213:00MDW - SYD
2 stops24h 50mDelta
Deal found 15/10$2,617

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 17 October 2025.

Return from

$1,407

One-way from

$1,149

Popular in

December

Cheapest in

March

Average price

$1,729
1/11-16/11
  • 1/11-16/11
  • 4 total stops
  • 61h 30m total
  • Sydney to Chicago
Search Deals
16/11
  • 16/11
  • 3 total stops
  • 54h 58m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($434 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($75 potential savings vs. average return price).
Search Deals
Average for return flights in October 2025
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 17 October 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

Sat 1/11

11:20-12:30

2 stops41h 10m

Chicago Midway

Sun 16/11

06:30-09:00

2 stops33h 30m

$1,729

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 26/12

10:40-16:24

2 stops22h 44m

Chicago Midway

Tue 3/2

14:00-08:30

2 stops25h 30m

$2,145

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 26/12

10:40-17:19

2 stops47h 39m

Chicago Midway

Sun 1/2

13:05-06:50

2 stops24h 45m

$2,145

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 24/12

10:40-22:22

2 stops28h 42m

Chicago Midway

Tue 3/2

13:05-06:50

2 stops24h 45m

$2,219

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 26/12

10:40-16:24

2 stops22h 44m

Chicago Midway

Thu 5/2

13:00-06:50

2 stops24h 50m

$2,219

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 24/12

10:40-22:22

2 stops28h 42m

Chicago Midway

Wed 4/2

09:30-08:30

2 stops30h 00m

$2,219

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 26/12

10:40-16:24

2 stops22h 44m

Chicago Midway

Sat 7/2

13:00-06:50

2 stops24h 50m

$2,219

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 12/11

10:40-18:18

2 stops24h 38m

Chicago Midway

Wed 19/11

13:47-08:30

2 stops25h 43m

$2,368

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 16/11

10:40-16:38

2 stops22h 58m

Chicago Midway

Sun 30/11

09:41-08:30

2 stops29h 49m

$2,456

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/11

10:40-17:43

2 stops24h 03m

Chicago Midway

Mon 17/11

10:47-08:30

2 stops28h 43m

$2,524

Flights are sorted by cheapest return flights first.

Deals found on 16/10

Showing 1-10 of 19 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 58 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, Sydney Kingsford Smith offers the quickest one-way flight (22 hours 58 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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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.

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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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