$764+ 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 15/10. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
6 Sep — 13 Sep1
1 adult

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 1 September 2025.

Return from

$1,484

One-way from

$764

Popular in

December

Cheapest in

February

Average price

$1,844
Qantas Airways
  • Qantas Airways
  • 16/10-23/10
  • 2 total stops
  • 43h 44m total
  • Sydney to Chicago
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15/10
  • 15/10
  • 3 total stops
  • 47h 16m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($701 potential increase over avg. return price).
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Cheapest flight prices on average. 4% potential price decrease ($115 potential savings vs. average return price).
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Average for return flights in September 2025
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Find flight deals to Midway Airport

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 September 2025.

Thu 25/1214:15SYD - MDW
2 stops25h 01mDelta
Thu 15/109:30MDW - SYD
2 stops28h 20mDelta
Deal found 31/8$2,149
Tue 14/1010:25SYD - MDW
2 stops24h 00mDelta
Tue 21/1010:35MDW - SYD
2 stops29h 00mDelta
Deal found 30/8$2,372
Tue 30/909:25SYD - MDW
2 stops27h 11mDelta
Wed 12/1112:47MDW - SYD
2 stops26h 43mDelta
Deal found 1/9$2,373
Thu 16/1010:25SYD - MDW
2 stops24h 00mDelta
Thu 23/1013:48MDW - SYD
2 stops25h 47mDelta
Deal found 31/8$2,448
Mon 8/909:25SYD - MDW
2 stops23h 12mDelta
Tue 23/910:35MDW - SYD
2 stops29h 00mDelta
Deal found 30/8$2,521
Wed 10/909:25SYD - MDW
2 stops23h 12mDelta
Mon 3/1113:08MDW - SYD
2 stops26h 22mDelta
Deal found 31/8$2,523
Sun 16/1110:40SYD - MDW
2 stops24h 28mDelta
Thu 20/1109:32MDW - SYD
2 stops29h 58mDelta
Deal found 31/8$2,673
Thu 9/1010:25SYD - MDW
2 stops27h 49mDelta
Mon 13/1013:08MDW - SYD
2 stops26h 27mDelta
Deal found 1/9$2,772
Fri 19/1210:40SYD - MDW
2 stops22h 56mDelta
Wed 7/109:20MDW - SYD
2 stops30h 10mDelta
Deal found 31/8$2,784
Thu 18/909:25SYD - MDW
2 stops23h 10mDelta
Thu 16/1009:20MDW - SYD
2 stops30h 15mDelta
Deal found 1/9$2,864
Thu 11/909:25SYD - MDW
2 stops24h 10mDelta
Mon 13/1013:08MDW - SYD
2 stops26h 27mDelta
Deal found 31/8$2,987
Sun 14/1210:40SYD - MDW
2 stops29h 52mDelta
Fri 2/111:48MDW - SYD
2 stops27h 42mDelta
Deal found 30/8$3,307

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 September 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 25/12

14:15-22:16

2 stops25h 01m

Chicago Midway

Thu 15/1

09:30-06:50

2 stops28h 20m

$2,149

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 14/10

10:25-17:43

2 stops23h 18m

Chicago Midway

Tue 21/10

10:35-07:35

2 stops29h 00m

$2,372

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 30/9

09:25-17:35

2 stops23h 10m

Chicago Midway

Wed 12/11

09:41-08:30

2 stops29h 49m

$2,372

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 15/10

10:25-18:25

2 stops24h 00m

Chicago Midway

Wed 22/10

13:08-07:35

2 stops26h 27m

$2,373

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 8/10

10:25-22:14

2 stops27h 49m

Chicago Midway

Wed 15/10

13:48-07:35

2 stops25h 47m

$2,373

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 16/10

10:25-18:25

2 stops24h 00m

Chicago Midway

Thu 23/10

13:48-07:35

2 stops25h 47m

$2,448

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 27/9

09:25-18:35

2 stops24h 10m

Chicago Midway

Sat 4/10

13:43-07:35

2 stops25h 52m

$2,521

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 16/10

10:25-18:25

2 stops24h 00m

Chicago Midway

Wed 22/10

12:48-07:35

2 stops26h 47m

$2,521

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 1/10

09:25-17:35

2 stops23h 10m

Chicago Midway

Tue 7/10

12:48-07:35

2 stops26h 47m

$2,523

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 15/10

17:20-00:36

3 stops47h 16m

$764

Flights are sorted by cheapest return flights first.

Deals found on 30/8

Showing 1-10 of 14 results
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 12 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 43 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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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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