$1,101+ Cheap flights to Midway

— MDW
25 Sep — 2 Oct1
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

Thu 8/1010:10 -
2 stops29h 33m
Wed 21/1006:15 -
2 stops33h 50m
Deal found 23/8$1,480
Wed 14/1010:10 -
2 stops29h 33m
Fri 30/1006:16 -
2 stops34h 44m
Deal found 23/8$1,515
Fri 2/1009:10 -
2 stops29h 34m
Thu 15/1013:12 -
2 stops26h 18m
Deal found 24/8$1,671
Sun 27/909:30 -
2 stops29h 14m
Mon 28/906:25 -
2 stops33h 35m
Deal found 25/8$1,814
Mon 24/809:10 -
2 stops26h 21m
Mon 7/906:05 -
2 stops34h 00m
Deal found 23/8$1,924
Wed 23/909:15 -
2 stops24h 04m
Wed 30/913:19 -
2 stops26h 31m
Deal found 26/8$2,256
Thu 17/909:15 -
2 stops24h 18m
Wed 14/1009:29 -
2 stops30h 21m
Deal found 25/8$2,257
Sat 10/1010:15 -
2 stops23h 45m
Mon 26/1013:27 -
2 stops26h 03m
Deal found 25/8$2,332
Thu 3/1210:40 -
2 stops23h 10m
Sun 13/1210:24 -
2 stops29h 06m
Deal found 23/8$2,444
Fri 4/1210:40 -
2 stops24h 21m
Sun 13/1210:24 -
2 stops29h 06m
Deal found 23/8$2,480

Find flight deals to Midway Airport

Return from

$1,314

One-way from

$1,101

Popular in

May

Cheapest in

October

Average price

$1,676
8/10-21/10
  • 8/10-21/10
  • 6 total stops
  • 91h 17m total
  • Sydney to Chicago
Search Deals
15/10
  • 15/10
  • 3 total stops
  • 49h 28m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($223 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($54 potential savings vs. average return price).
Search Deals
Average for return flights in August 2026
Search Deals

Cheapflights Fare Finder

 
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 Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 23/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Wed 30/9

13:19-06:50

2 stops26h 31m

$2,256

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 17/9

09:15-18:33

2 stops24h 18m

Chicago Midway

Wed 14/10

09:29-07:50

2 stops30h 21m

$2,257

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 14/10

10:15-18:00

2 stops23h 45m

Chicago Midway

Wed 28/10

13:27-07:30

2 stops26h 03m

$2,257

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 12/10

10:15-18:00

2 stops23h 45m

Chicago Midway

Sat 24/10

13:27-07:30

2 stops26h 03m

$2,514

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 8/10

10:15-16:47

2 stops22h 32m

Chicago Midway

Wed 21/10

10:59-07:50

2 stops28h 51m

$2,742
Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 7/10

10:15-16:47

2 stops22h 32m

Chicago Midway

Wed 14/10

13:27-07:50

2 stops26h 23m

$2,743

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 19/9

09:15-18:22

2 stops24h 07m

Chicago Midway

Sat 26/9

13:19-06:50

2 stops26h 31m

$2,888

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 22/12

14:15-22:22

2 stops25h 07m

Chicago Midway

Tue 12/1

12:30-06:50

2 stops25h 20m

$2,894
Cheapest one-way

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 16/10

14:15-23:43

3 stops49h 28m

$1,120

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 8/9

20:45-17:51

3 stops36h 06m

$1,391

Flights are sorted by cheapest return flights first.

Deals found on 25/8

Showing 1-10 of 20 resultsSorted by cheapest first
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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

Cheapflights Insights

Everything you need to know about your flight to Chicago Midway Airport

Rainfall in Midway 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

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 45 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 (23 hours 33 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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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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