$708+ Cheap flights to Midway

— MDW
12 Oct — 19 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

Tue 3/1110:40 -
2 stops24h 20m
Sun 8/1109:29 -
2 stops30h 01m
Deal found 7/9$2,254
Thu 17/909:15 -
2 stops24h 18m
Wed 30/913:19 -
2 stops26h 31m
Deal found 8/9$2,255
Mon 5/1010:15 -
2 stops24h 18m
Mon 19/1013:27 -
2 stops26h 23m
Deal found 9/9$2,257
Fri 23/1010:15 -
2 stops22h 32m
Fri 30/1010:59 -
2 stops28h 31m
Deal found 8/9$2,407
Mon 5/1010:15 -
2 stops24h 18m
Sun 18/1010:59 -
2 stops28h 51m
Deal found 8/9$2,584
Fri 25/909:15 -
2 stops28h 29m
Mon 5/1009:29 -
2 stops30h 21m
Deal found 9/9$2,660
Fri 25/1210:40 -
2 stops23h 44m
Sat 9/113:00 -
2 stops26h 30m
Deal found 10/9$2,667
Thu 8/1010:15 -
2 stops23h 45m
Wed 21/1013:27 -
2 stops26h 23m
Deal found 9/9$2,683
Thu 5/1110:40 -
2 stops23h 07m
Mon 9/1113:05 -
2 stops26h 25m
Deal found 7/9$2,741
Tue 27/1009:40 -
2 stops24h 20m
Tue 3/1112:27 -
2 stops27h 03m
Deal found 11/9$2,743
Mon 26/1009:40 -
2 stops23h 07m
Mon 2/1111:38 -
2 stops27h 52m
Deal found 10/9$2,750
Thu 1/1009:15 -
2 stops24h 18m
Mon 26/1012:27 -
2 stops27h 03m
Deal found 11/9$2,901

Find flight deals to Midway Airport

Return from

$1,293

One-way from

$708

Popular in

May

Cheapest in

October

Average price

$1,760
Air Canada
  • Air Canada
  • 28/10-24/11
  • 3 total stops
  • 55h 39m total
  • Sydney to Chicago
Search Deals
21/10-31/12
  • 21/10-31/12
  • 3 total stops
  • 49h 28m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($153 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($49 potential savings vs. average return price).
Search Deals
Average for return flights in September 2026
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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 21/10

14:15-23:43

3 stops49h 28m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$708

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 5/10

12:15-17:46

3 stops45h 31m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,438

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 22/10

18:50-12:17

2 stops33h 27m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,644

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 1/3

11:30-05:55

2 stops35h 25m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,688

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 8/10

10:15-18:00

2 stops23h 45m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,748

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 8/10

16:10-12:17

3 stops36h 07m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,780
Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 31/12

10:40-17:24

2 stops23h 44m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,827

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sun 27/12

11:15-19:02

2 stops48h 47m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$2,158

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 3/11

10:40-18:00

2 stops24h 20m

Chicago Midway

Sun 8/11

09:29-08:30

2 stops30h 01m

$2,254

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 3/11

10:40-16:47

2 stops23h 07m

Chicago Midway

Mon 9/11

12:30-08:30

2 stops27h 00m

$2,254

Flights are sorted by cheapest return flights first.

Deals found on 8/9

Showing 1-10 of 21 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 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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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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