$991+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
31 Jul — 7 Aug1
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 1 July 2026.

Mon 3/813:15
SYD
-
MDW
3 stops36h 52m
Multiple Airlines
Wed 19/806:05
MDW
-
SYD
3 stops38h 45m
Multiple Airlines
Deal found 29/6$1,336
Thu 13/809:10
SYD
-
MDW
2 stops26h 22m
Multiple Airlines
Thu 20/806:05
MDW
-
SYD
2 stops34h 25m
Multiple Airlines
Deal found 29/6$1,661
Sun 19/709:10
SYD
-
MDW
2 stops26h 22m
Multiple Airlines
Mon 3/806:05
MDW
-
SYD
2 stops34h 25m
Multiple Airlines
Deal found 28/6$1,781
Thu 23/709:10
SYD
-
MDW
2 stops26h 22m
Multiple Airlines
Wed 5/811:06
MDW
-
SYD
2 stops29h 24m
Multiple Airlines
Deal found 30/6$1,782
Thu 1/1009:15
SYD
-
MDW
2 stops24h 04m
Delta
Fri 9/1009:29
MDW
-
SYD
2 stops30h 21m
Delta
Deal found 29/6$1,987
Wed 11/1110:40
SYD
-
MDW
2 stops23h 10m
Delta
Sun 15/1112:30
MDW
-
SYD
2 stops27h 00m
Delta
Deal found 29/6$2,102
Mon 20/709:15
SYD
-
MDW
2 stops24h 03m
Delta
Sun 2/811:05
MDW
-
SYD
2 stops28h 45m
Delta
Deal found 27/6$2,377
Tue 11/809:15
SYD
-
MDW
2 stops24h 18m
Delta
Wed 19/813:25
MDW
-
SYD
2 stops26h 25m
Delta
Deal found 28/6$2,379

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 1 July 2026.

Return from

$1,336

One-way from

$991

Popular in

May

Cheapest in

August

Average price

$1,961
3/8-19/8
  • 3/8-19/8
  • 6 total stops
  • 75h 37m total
  • Sydney to Chicago
Search Deals
Delta
  • Delta
  • 7/9
  • 2 total stops
  • 24h 18m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($182 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($23 potential savings vs. average return price).
Search Deals
Average for return flights in July 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 1 July 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

Thu 23/7

09:10-20:32

2 stops26h 22m

Chicago Midway

Wed 5/8

11:06-07:30

2 stops29h 24m

$1,782

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 20/7

09:15-18:18

2 stops24h 03m

Chicago Midway

Sun 2/8

11:05-06:50

2 stops28h 45m

$2,377

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 11/8

09:15-18:33

2 stops24h 18m

Chicago Midway

Wed 19/8

13:25-06:50

2 stops26h 25m

$2,379

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 30/7

09:15-18:18

2 stops24h 03m

Chicago Midway

Thu 6/8

13:25-06:50

2 stops26h 25m

$2,448
Fastest return journey

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 12/8

09:15-18:01

2 stops23h 46m

Chicago Midway

Sat 22/8

13:51-06:50

2 stops25h 59m

$2,448

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/8

09:15-18:01

2 stops23h 46m

Chicago Midway

Wed 19/8

13:25-06:50

2 stops26h 25m

$2,748

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 5/8

09:15-18:01

2 stops23h 46m

Chicago Midway

Tue 11/8

13:25-06:50

2 stops26h 25m

$2,853

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 5/8

09:15-18:33

2 stops24h 18m

Chicago Midway

Mon 10/8

13:25-06:50

2 stops26h 25m

$2,853

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 25/7

09:15-18:07

2 stops23h 52m

Chicago Midway

Sat 1/8

13:18-06:50

2 stops26h 32m

$3,379

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 10/7

09:15-18:25

2 stops24h 10m

Chicago Midway

Sun 26/7

12:41-06:50

2 stops27h 09m

$3,379

Flights are sorted by cheapest return flights first.

Deals found on 30/6

Showing 1-10 of 18 resultsSorted by cheapest first
1
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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 10 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 (23 hours 10 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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Search flights to Midway by cabin class

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First Class flights to Chicago Midway Airport
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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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