$965+ Cheap flights to Midway

— MDW
10 Dec — 17 Dec1
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 12/1110:40 -
2 stops22h 59m
Wed 25/1113:05 -
2 stops26h 25m
Deal found 6/11$3,006
Thu 19/1112:15 -
2 stops34h 40m
Wed 2/1215:45 -
2 stops33h 10m
Deal found 6/11$3,780
Wed 23/1214:05 -
2 stops26h 56m
Wed 30/1206:01 -
1 stop31h 54m
Deal found 8/11$3,950
Thu 19/1114:05 -
1 stop34h 18m
Wed 2/1210:21 -
1 stop27h 34m
Deal found 6/11$3,979
Thu 12/1114:05 -
1 stop38h 20m
Wed 25/1108:28 -
1 stop29h 27m
Deal found 6/11$4,034
Sat 5/1214:05 -
2 stops46h 37m
Sat 12/1210:40 -
1 stop27h 15m
Deal found 7/11$4,534
Thu 26/1112:15 -
2 stops34h 45m
Thu 3/1215:45 -
2 stops36h 30m
Deal found 9/11$4,537
Fri 18/1214:05 -
2 stops26h 56m
Fri 1/106:01 -
1 stop31h 54m
Deal found 10/11$4,830

Find flight deals to Midway Airport

Return from

$1,410

One-way from

$965

Popular in

May

Cheapest in

October

Average price

$1,760
Air Canada
  • Air Canada
  • 21/1-28/1
  • 3 total stops
  • 46h 52m total
  • Sydney to Chicago
Search Deals
5/3-31/12
  • 5/3-31/12
  • 3 total stops
  • 39h 13m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($158 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($50 potential savings vs. average return price).
Search Deals
Average for return flights in November 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

Thu 4/3

21:40-16:47

3 stops36h 07m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,321

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 29/3

10:30-23:46

2 stops53h 16m

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 4/3

13:35-22:45

2 stops26h 10m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,567

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 13/4

09:15-22:10

2 stops27h 55m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,575

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 26/11

10:40-22:54

2 stops29h 14m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,879

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 25/11

10:40-22:54

2 stops29h 14m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,886
Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 4/12

10:40-18:01

2 stops24h 21m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,914

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sun 18/4

09:15-18:37

2 stops24h 22m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$2,102

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 10/12

14:05-10:05

1 stop37h 00m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$2,144

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 21/12

10:40-11:01

2 stops41h 21m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$2,189

Flights are sorted by cheapest return flights first.

Deals found on 6/11

Showing 1-10 of 22 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 26 hours 56 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.

  • What is the cheapest airport to fly to in Midway?

    Chicago Midway is currently the cheapest airport to fly to in Midway. One-way flights to Chicago Midway typically cost $227, while return flights cost around $234.

  • How much is a return flight to Midway?

    A return flight to Midway will typically cost around $249, however they can be found for as little as $234.

  • 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 (26 hours 37 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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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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