$1,100+ 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 22/11. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
14 Dec — 21 Dec1
1 adult
1 adult, Economy, 0 bags

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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 14 November 2025.

Sun 28/1210:40SYD - MDW
2 stops22h 40mDelta
Sun 4/109:50MDW - SYD
2 stops28h 00mDelta
Deal found 13/11$2,442
Thu 13/1110:40SYD - MDW
2 stops24h 38mDelta
Wed 26/1113:15MDW - SYD
2 stops26h 15mDelta
Deal found 12/11$2,513
Mon 17/1110:40SYD - MDW
2 stops24h 38mDelta
Sun 30/1109:34MDW - SYD
2 stops29h 56mDelta
Deal found 13/11$2,516
Fri 14/1110:40SYD - MDW
2 stops24h 38mDelta
Thu 27/1110:47MDW - SYD
2 stops28h 43mDelta
Deal found 12/11$2,663
Fri 14/1110:40SYD - MDW
2 stops24h 28mDelta
Fri 21/1112:47MDW - SYD
2 stops26h 43mDelta
Deal found 13/11$2,666
Thu 13/1108:30SYD - MDW
2 stops29h 14mMultiple Airlines
Wed 26/1105:30MDW - SYD
1 stop32h 25mMultiple Airlines
Deal found 12/11$2,869
Tue 30/1214:15SYD - MDW
2 stops25h 07mDelta
Sat 10/109:34MDW - SYD
2 stops28h 16mDelta
Deal found 12/11$3,055
Fri 12/1210:40SYD - MDW
2 stops24h 38mDelta
Sat 10/109:34MDW - SYD
2 stops28h 16mDelta
Deal found 12/11$3,148
Sun 14/1210:40SYD - MDW
2 stops30h 07mDelta
Fri 2/109:50MDW - SYD
2 stops29h 40mDelta
Deal found 12/11$3,470
Thu 25/1214:15SYD - MDW
2 stops25h 07mDelta
Fri 23/112:48MDW - SYD
2 stops26h 42mDelta
Deal found 13/11$4,558

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 14 November 2025.

Return from

$1,491

One-way from

$1,100

Popular in

December

Cheapest in

March

Average price

$1,762
Air New Zealand
  • Air New Zealand
  • 2/2-8/2
  • 4 total stops
  • 52h 42m total
  • Sydney to Chicago
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22/11
  • 22/11
  • 2 total stops
  • 35h 13m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($369 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($60 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 14 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

Thu 19/2

14:15-22:44

2 stops25h 29m

Chicago Midway

Mon 2/3

09:34-08:30

2 stops29h 56m

$2,290

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 28/12

10:40-16:20

2 stops22h 40m

Chicago Midway

Sun 4/1

09:50-06:50

2 stops28h 00m

$2,442

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

$2,513

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 2/2

10:40-17:55

2 stops24h 15m

Chicago Midway

Sun 8/2

13:28-08:30

2 stops26h 02m

$2,513

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 30/12

14:15-22:22

2 stops25h 07m

Chicago Midway

Sat 10/1

09:34-06:50

2 stops28h 16m

$3,055

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 12/12

10:40-18:18

2 stops24h 38m

Chicago Midway

Sat 10/1

09:34-06:50

2 stops28h 16m

$3,148

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 14/12

10:40-23:47

2 stops30h 07m

Chicago Midway

Fri 2/1

09:50-08:30

2 stops29h 40m

$3,470

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 25/12

14:15-22:22

2 stops25h 07m

Chicago Midway

Fri 23/1

12:48-08:30

2 stops26h 42m

$4,558

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 13/12

10:40-18:18

2 stops24h 38m

Chicago Midway

Wed 24/12

09:29-08:30

2 stops30h 01m

$12,781

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 22/11

06:00-00:13

2 stops35h 13m

$1,100

Flights are sorted by cheapest return flights first.

Deals found on 13/11

Showing 1-10 of 18 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, Brisbane offers the quickest one-way flight (22 hours 39 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?

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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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