$1,131+ 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 14/11. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
7 Dec — 14 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals to Midway Airport

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 7 November 2025.

Tue 9/1210:40SYD - MDW
2 stops30h 07mDelta
Sun 14/1209:59MDW - SYD
2 stops29h 31mDelta
Deal found 5/11$2,137
Wed 10/1210:40SYD - MDW
2 stops30h 07mDelta
Mon 15/1209:34MDW - SYD
2 stops29h 56mDelta
Deal found 6/11$2,522
Tue 25/1110:40SYD - MDW
2 stops22h 58mDelta
Tue 30/1212:45MDW - SYD
2 stops25h 05mDelta
Deal found 6/11$2,525
Sun 23/1110:40SYD - MDW
2 stops24h 28mDelta
Sun 30/1113:47MDW - SYD
2 stops25h 43mDelta
Deal found 5/11$2,602
Tue 25/1119:15SYD - MDW
2 stops44h 02mMultiple Airlines
Tue 30/1208:00MDW - SYD
1 stop29h 55mMultiple Airlines
Deal found 6/11$2,918
Sat 6/1210:40SYD - MDW
2 stops30h 07mDelta
Sat 13/1209:59MDW - SYD
2 stops29h 31mDelta
Deal found 6/11$3,072
Sun 14/1210:40SYD - MDW
2 stops22h 38mDelta
Fri 2/106:00MDW - SYD
2 stops33h 30mDelta
Deal found 5/11$3,189
Mon 22/1214:15SYD - MDW
2 stops25h 07mDelta
Mon 29/1206:00MDW - SYD
2 stops33h 30mDelta
Deal found 6/11$3,723
Fri 12/1210:40SYD - MDW
2 stops24h 38mDelta
Sun 28/1211:48MDW - SYD
2 stops26h 02mDelta
Deal found 5/11$4,073
Sat 20/1210:40SYD - MDW
2 stops28h 42mDelta
Sat 27/1211:48MDW - SYD
2 stops26h 02mDelta
Deal found 5/11$4,236

Flights to Midway in 2025

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 7 November 2025.

Return from

$1,562

One-way from

$1,131

Popular in

December

Cheapest in

March

Average price

$1,777
Air New Zealand
  • Air New Zealand
  • 26/11-11/12
  • 4 total stops
  • 59h 07m total
  • Sydney to Chicago
Search Deals
14/11
  • 14/11
  • 3 total stops
  • 47h 04m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($413 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($66 potential savings vs. average return price).
Search Deals
Average for return flights in November 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 7 November 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

Tue 9/12

10:40-23:47

2 stops30h 07m

Chicago Midway

Sun 14/12

09:59-08:30

2 stops29h 31m

$2,137

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 10/12

10:40-23:47

2 stops30h 07m

Chicago Midway

Mon 15/12

09:34-08:30

2 stops29h 56m

$2,522

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 25/11

10:40-16:38

2 stops22h 58m

Chicago Midway

Tue 30/12

12:45-06:50

2 stops25h 05m

$2,525

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 23/4

09:25-18:31

2 stops24h 06m

Chicago Midway

Wed 29/4

10:35-06:35

2 stops29h 00m

$2,541

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 23/11

10:40-18:08

2 stops24h 28m

Chicago Midway

Sun 30/11

13:47-08:30

2 stops25h 43m

$2,602

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 24/4

09:25-18:05

2 stops23h 40m

Chicago Midway

Thu 30/4

13:00-06:35

2 stops26h 35m

$2,693

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 25/4

09:25-18:05

2 stops23h 40m

Chicago Midway

Fri 1/5

14:00-06:35

2 stops25h 35m

$2,693

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 25/11

19:15-22:17

2 stops44h 02m

Chicago Midway

Tue 30/12

08:00-06:55

1 stop29h 55m

$2,918

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 6/12

10:40-23:47

2 stops30h 07m

Chicago Midway

Sat 13/12

09:59-08:30

2 stops29h 31m

$3,072

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 14/12

10:40-16:18

2 stops22h 38m

Chicago Midway

Fri 2/1

06:00-08:30

2 stops33h 30m

$3,189

Flights are sorted by cheapest return flights first.

Deals found on 6/11

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 22 hours 58 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 58 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.

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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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