$1,150+ 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 26/5. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
17 Apr — 24 Apr1
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 18 March 2026.

Wed 29/409:15
SYD
-
MDW
2 stops23h 43m
Delta
Wed 6/512:52
MDW
-
SYD
2 stops26h 58m
Delta
Deal found 15/3$2,120
Tue 28/409:15
SYD
-
MDW
2 stops23h 43m
Delta
Tue 5/513:24
MDW
-
SYD
2 stops26h 26m
Delta
Deal found 14/3$2,135
Tue 14/709:15
SYD
-
MDW
2 stops24h 16m
Delta
Tue 15/914:00
MDW
-
SYD
2 stops25h 50m
Delta
Deal found 13/3$2,151
Fri 1/512:00
SYD
-
MDW
1 stop24h 37m
Multiple Airlines
Fri 8/515:07
MDW
-
SYD
1 stop24h 48m
Multiple Airlines
Deal found 17/3$2,173
Thu 30/409:15
SYD
-
MDW
2 stops24h 21m
Delta
Thu 7/513:22
MDW
-
SYD
2 stops26h 28m
Delta
Deal found 16/3$2,192
Sat 16/509:15
SYD
-
MDW
2 stops24h 18m
Delta
Fri 5/612:53
MDW
-
SYD
2 stops26h 57m
Delta
Deal found 16/3$2,261
Fri 10/709:15
SYD
-
MDW
2 stops24h 16m
Delta
Sun 26/714:00
MDW
-
SYD
2 stops25h 50m
Delta
Deal found 15/3$2,265
Mon 13/709:15
SYD
-
MDW
2 stops38h 23m
Delta
Wed 26/813:05
MDW
-
SYD
2 stops50h 45m
Delta
Deal found 17/3$2,291
Mon 20/409:15
SYD
-
MDW
2 stops28h 13m
Delta
Sun 3/510:41
MDW
-
SYD
2 stops29h 09m
Delta
Deal found 15/3$2,303
Fri 3/709:15
SYD
-
MDW
2 stops38h 23m
Delta
Tue 21/710:35
MDW
-
SYD
2 stops53h 15m
Delta
Deal found 14/3$2,341

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 18 March 2026.

Return from

$1,272

One-way from

$1,245

Popular in

December

Cheapest in

August

Average price

$1,568
Air Canada
  • Air Canada
  • 20/4-30/4
  • 2 total stops
  • 45h 05m total
  • Sydney to Chicago
Search Deals
29/5
  • 29/5
  • 2 total stops
  • 56h 42m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($72 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($22 potential savings vs. average return price).
Search Deals
Average for return flights in March 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 18 March 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

Mon 4/5

09:15-17:58

2 stops23h 43m

Chicago Midway

Mon 18/5

13:22-06:50

2 stops26h 28m

$2,120
Fastest return journey

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 14/7

09:15-18:31

2 stops24h 16m

Chicago Midway

Tue 15/9

14:00-06:50

2 stops25h 50m

$2,151

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 10/7

09:15-18:31

2 stops24h 16m

Chicago Midway

Sun 26/7

14:00-06:50

2 stops25h 50m

$2,265

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 13/7

09:15-08:38

2 stops38h 23m

Chicago Midway

Wed 26/8

13:05-06:50

2 stops50h 45m

$2,291

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 3/7

09:15-08:38

2 stops38h 23m

Chicago Midway

Thu 23/7

18:45-06:50

2 stops45h 05m

$2,355

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 12/7

09:15-18:31

2 stops24h 16m

Chicago Midway

Wed 26/8

13:05-06:50

2 stops50h 45m

$2,371

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 17/7

09:15-18:05

2 stops23h 50m

Chicago Midway

Wed 26/8

13:05-06:50

2 stops50h 45m

$2,371

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 2/5

09:15-17:58

2 stops23h 43m

Chicago Midway

Sat 9/5

13:22-06:50

2 stops26h 28m

$2,374

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 1/7

09:15-08:38

2 stops38h 23m

Chicago Midway

Tue 21/7

14:00-06:50

2 stops25h 50m

$2,416

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 12/6

09:15-18:31

2 stops24h 16m

Chicago Midway

Sun 12/7

14:00-06:50

2 stops25h 50m

$2,492

Flights are sorted by cheapest return flights first.

Deals found on 13/3

Showing 1-10 of 18 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 43 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 (23 hours 31 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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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?

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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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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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