$1,000+ 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 13/5. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
29 Mar — 5 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 27 February 2026.

Thu 19/309:40
SYD
-
MDW
2 stops25h 00m
Delta
Tue 21/413:24
MDW
-
SYD
2 stops26h 26m
Delta
Deal found 24/2$1,714
Thu 5/310:40
SYD
-
MDW
2 stops24h 05m
Delta
Wed 18/313:10
MDW
-
SYD
2 stops26h 15m
Delta
Deal found 26/2$1,770
Sat 2/509:15
SYD
-
MDW
2 stops28h 13m
Delta
Tue 16/614:00
MDW
-
SYD
2 stops25h 50m
Delta
Deal found 27/2$1,788
Sun 1/310:40
SYD
-
MDW
2 stops24h 05m
Delta
Sat 28/313:10
MDW
-
SYD
2 stops26h 40m
Delta
Deal found 23/2$1,798
Fri 12/609:15
SYD
-
MDW
2 stops27h 30m
Delta
Sun 12/714:00
MDW
-
SYD
2 stops25h 50m
Delta
Deal found 25/2$1,995
Fri 17/412:00
SYD
-
MDW
1 stop24h 37m
Multiple Airlines
Thu 23/416:15
MDW
-
SYD
2 stops28h 35m
Multiple Airlines
Deal found 25/2$2,064
Fri 10/709:15
SYD
-
MDW
2 stops23h 50m
Delta
Sun 26/714:00
MDW
-
SYD
2 stops25h 50m
Delta
Deal found 25/2$2,124
Mon 1/609:15
SYD
-
MDW
2 stops24h 18m
Delta
Fri 31/713:00
MDW
-
SYD
2 stops26h 50m
Delta
Deal found 24/2$2,128
Sun 2/809:15
SYD
-
MDW
2 stops23h 50m
Delta
Sun 30/814:00
MDW
-
SYD
2 stops25h 50m
Delta
Deal found 23/2$2,133
Sun 12/709:15
SYD
-
MDW
2 stops24h 16m
Delta
Fri 31/713:05
MDW
-
SYD
2 stops26h 45m
Delta
Deal found 23/2$2,209

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 27 February 2026.

Return from

$1,563

One-way from

$1,000

Popular in

December

Cheapest in

April

Average price

$1,517
Air New Zealand
  • Air New Zealand
  • 10/3-17/3
  • 4 total stops
  • 54h 08m total
  • Sydney to Chicago
Search Deals
13/5
  • 13/5
  • 3 total stops
  • 50h 21m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($235 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($38 potential savings vs. average return price).
Search Deals
Average for return flights in February 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 27 February 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

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 1/6

09:15-17:56

2 stops23h 41m

Chicago Midway

Fri 31/7

09:20-06:50

2 stops30h 30m

$1,788

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 2/5

09:15-22:28

2 stops28h 13m

Chicago Midway

Tue 16/6

14:00-06:50

2 stops25h 50m

$1,788

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 10/7

09:15-18:05

2 stops23h 50m

Chicago Midway

Sun 26/7

14:00-06:50

2 stops25h 50m

$2,124

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 13/4

09:15-18:36

2 stops24h 21m

Chicago Midway

Mon 20/4

09:29-06:50

2 stops30h 21m

$2,144

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 12/7

09:15-18:31

2 stops24h 16m

Chicago Midway

Fri 31/7

13:05-06:50

2 stops26h 45m

$2,209

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 10/3

09:40-17:54

2 stops24h 14m

Chicago Midway

Tue 17/3

13:10-06:05

2 stops24h 55m

$2,497

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 17/4

09:15-17:58

2 stops23h 43m

Chicago Midway

Thu 23/4

09:29-06:50

2 stops30h 21m

$2,663

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 10/3

13:15-22:31

2 stops25h 16m

Chicago Midway

Fri 13/3

12:47-07:30

2 stops26h 43m

$2,888

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 12/4

09:15-18:40

2 stops24h 25m

Chicago Midway

Sun 19/4

09:29-06:50

2 stops30h 21m

$2,980

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 7/4

09:15-17:54

2 stops23h 39m

Chicago Midway

Mon 12/10

13:05-07:50

2 stops26h 45m

$2,989

Flights are sorted by cheapest return flights first.

Deals found on 25/2

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 50 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 (21 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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