$1,119+ 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 15/1. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
30 Jan — 6 Feb1
1 adult
1 adult, Economy, 0 bags

Flights to Midway in 2025

Enter your travel dates to find the best prices.

Best flights to Midway Airport
Discover carefully curated flight deals to Midway Airport that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 31 December 2025.

Mon 19/110:40SYD - MDW
2 stops23h 49mDelta
Mon 2/213:26MDW - SYD
2 stops26h 04mDelta
Deal found 30/12$1,734
Fri 12/609:15SYD - MDW
2 stops24h 16mDelta
Sun 12/714:00MDW - SYD
2 stops25h 35mDelta
Deal found 29/12$2,152
Sat 2/509:15SYD - MDW
2 stops24h 30mDelta
Sun 10/513:05MDW - SYD
2 stops26h 30mDelta
Deal found 31/12$2,152
Sun 19/409:15SYD - MDW
2 stops24h 30mDelta
Sun 26/413:10MDW - SYD
2 stops26h 25mDelta
Deal found 31/12$2,152
Fri 1/509:15SYD - MDW
2 stops23h 39mDelta
Wed 20/513:05MDW - SYD
2 stops26h 30mDelta
Deal found 29/12$2,158
Sat 9/509:15SYD - MDW
2 stops27h 30mDelta
Sat 23/514:00MDW - SYD
2 stops25h 35mDelta
Deal found 31/12$2,228
Thu 5/210:40SYD - MDW
2 stops24h 15mDelta
Wed 18/213:49MDW - SYD
2 stops25h 41mDelta
Deal found 30/12$2,378
Thu 12/210:40SYD - MDW
2 stops24h 05mDelta
Thu 19/212:45MDW - SYD
2 stops25h 05mDelta
Deal found 29/12$2,458
Sat 14/214:15SYD - MDW
2 stops25h 16mDelta
Sat 21/213:28MDW - SYD
2 stops26h 02mDelta
Deal found 31/12$2,530

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 31 December 2025.

Return from

$1,522

One-way from

$1,405

Popular in

December

Cheapest in

March

Average price

$2,051
Air Canada
  • Air Canada
  • 5/2-18/2
  • 3 total stops
  • 52h 57m total
  • Sydney to Chicago
Search Deals
13/2
  • 13/2
  • 2 total stops
  • 32h 09m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($351 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($55 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 31 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

Mon 19/1

10:40-17:29

2 stops23h 49m

Chicago Midway

Mon 2/2

13:26-08:30

2 stops26h 04m

$1,734

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 12/6

09:15-18:31

2 stops24h 16m

Chicago Midway

Sun 12/7

14:00-06:35

2 stops25h 35m

$2,152

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 2/5

09:15-18:45

2 stops24h 30m

Chicago Midway

Sun 10/5

13:05-06:35

2 stops26h 30m

$2,152

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 19/4

09:15-18:45

2 stops24h 30m

Chicago Midway

Sun 26/4

13:10-06:35

2 stops26h 25m

$2,152

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 1/5

09:15-17:54

2 stops23h 39m

Chicago Midway

Wed 20/5

13:05-06:35

2 stops26h 30m

$2,158

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 9/5

09:15-21:45

2 stops27h 30m

Chicago Midway

Sat 23/5

14:00-06:35

2 stops25h 35m

$2,228

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 5/2

10:40-17:55

2 stops24h 15m

Chicago Midway

Wed 18/2

13:49-08:30

2 stops25h 41m

$2,378

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 12/2

10:40-17:45

2 stops24h 05m

Chicago Midway

Thu 19/2

12:45-06:50

2 stops25h 05m

$2,458

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 14/2

14:15-22:31

2 stops25h 16m

Chicago Midway

Sat 21/2

13:28-08:30

2 stops26h 02m

$2,530

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 15/1

17:45-11:47

2 stops35h 02m

$1,119

Flights are sorted by cheapest return flights first.

Deals found on 31/12

Showing 1-10 of 14 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 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, Sydney Kingsford Smith offers the quickest one-way flight (22 hours 40 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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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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