$1,173+ 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 22/1. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
8 Jan — 15 Jan1
1 adult
1 adult, Economy, 0 bags

Flights to Midway in 2025

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 9 December 2025.

Thu 25/1210:40SYD - MDW
2 stops28h 42mDelta
Thu 22/110:48MDW - SYD
2 stops27h 02mDelta
Deal found 8/12$1,807
Sun 14/1210:40SYD - MDW
2 stops30h 07mDelta
Fri 2/111:48MDW - SYD
2 stops27h 42mDelta
Deal found 8/12$3,313
Sat 20/1210:40SYD - MDW
2 stops28h 42mDelta
Sat 3/111:48MDW - SYD
2 stops27h 42mDelta
Deal found 7/12$3,957

Find flight deals to Midway Airport

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 9 December 2025.

Return from

$1,607

One-way from

$1,173

Popular in

December

Cheapest in

March

Average price

$2,207
Air Canada
  • Air Canada
  • 26/1-8/2
  • 4 total stops
  • 84h 06m total
  • Sydney to Chicago
Search Deals
22/1
  • 22/1
  • 3 total stops
  • 49h 34m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($365 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($68 potential savings vs. average return price).
Search Deals
Average for return flights in December 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 9 December 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

Thu 25/12

10:40-22:22

2 stops28h 42m

Chicago Midway

Thu 22/1

10:48-06:50

2 stops27h 02m

$1,807

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 27/2

10:40-18:37

2 stops24h 57m

Chicago Midway

Fri 13/3

14:03-07:30

2 stops25h 27m

$1,884

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 11/5

09:25-18:05

2 stops23h 40m

Chicago Midway

Mon 8/6

13:00-06:35

2 stops26h 35m

$2,076

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 2/6

09:25-18:05

2 stops23h 40m

Chicago Midway

Tue 4/8

14:00-06:35

2 stops25h 35m

$2,076

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 7/3

10:40-22:42

2 stops29h 02m

Chicago Midway

Sat 14/3

14:03-07:25

2 stops25h 22m

$2,225

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 21/1

10:40-17:29

2 stops23h 49m

Chicago Midway

Wed 28/1

09:50-08:30

2 stops29h 40m

$2,376

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 26/1

10:40-17:29

2 stops23h 49m

Chicago Midway

Sun 8/2

10:48-06:50

2 stops27h 02m

$2,376

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 27/1

10:40-17:29

2 stops23h 49m

Chicago Midway

Sun 1/2

13:26-08:30

2 stops26h 04m

$2,526

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 20/12

10:40-22:22

2 stops28h 42m

Chicago Midway

Sat 3/1

11:48-08:30

2 stops27h 42m

$3,957

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 6/1

14:15-22:07

2 stops24h 52m

Chicago Midway

Tue 13/1

13:28-06:50

2 stops24h 22m

$4,745

Flights are sorted by cheapest return flights first.

Deals found on 7/12

Showing 1-10 of 21 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 23 hours 40 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, Brisbane offers the quickest one-way flight (22 hours 50 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.

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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