Australia
AUD

$621+ Cheap flights to Midway

— MDW
6 Nov — 13 Nov1
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

Mon 5/1010:15 -
2 stops24h 04m
Mon 19/1013:27 -
2 stops26h 23m
Deal found 2/10$1,061
Tue 17/1110:40 -
2 stops22h 59m
Tue 24/1110:34 -
2 stops28h 56m
Deal found 3/10$1,062
Tue 3/1110:40 -
2 stops23h 07m
Tue 10/1111:27 -
2 stops28h 03m
Deal found 4/10$1,063
Mon 2/1114:05 -
1 stop38h 17m
Mon 9/1112:20 -
2 stops49h 05m
Deal found 5/10$2,997
Mon 26/1008:45 -
2 stops42h 37m
Mon 2/1112:20 -
1 stop25h 35m
Deal found 6/10$3,127
Tue 3/1114:05 -
1 stop38h 17m
Tue 10/1112:27 -
2 stops48h 58m
Deal found 4/10$3,152
Thu 8/1013:00 -
1 stop39h 17m
Wed 21/1006:21 -
2 stops33h 09m
Deal found 5/10$3,282
Wed 4/1121:25 -
2 stops31h 00m
Wed 11/1112:27 -
1 stop25h 28m
Deal found 6/10$3,395
Fri 20/1110:40 -
2 stops22h 59m
Fri 27/1112:05 -
2 stops27h 25m
Deal found 6/10$3,559
Fri 20/1114:05 -
1 stop34h 32m
Fri 27/1108:51 -
1 stop29h 04m
Deal found 6/10$3,615
Mon 9/1114:05 -
1 stop38h 17m
Sun 22/1109:09 -
2 stops28h 16m
Deal found 6/10$3,636

Find flight deals to Midway Airport

Return from

$1,062

One-way from

$621

Popular in

May

Cheapest in

October

Average price

$1,479
Delta
  • Delta
  • 17/11-24/11
  • 4 total stops
  • 47h 47m total
  • Sydney to Chicago
Search Deals
Delta
  • Delta
  • 26/11-31/12
  • 2 total stops
  • 29h 14m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($163 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 October 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

Fri 16/10

10:15-08:44

2 stops38h 29m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$707

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 17/10

10:15-09:32

2 stops39h 17m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$707
Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 22/1

10:40-16:50

2 stops23h 10m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$707

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 17/11

10:40-16:39

2 stops22h 59m

Chicago Midway

Tue 24/11

10:34-08:30

2 stops28h 56m

$1,062

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 4/11

10:40-18:00

2 stops24h 20m

Chicago Midway

Wed 11/11

12:30-08:30

2 stops27h 00m

$1,063

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 3/11

10:40-16:47

2 stops23h 07m

Chicago Midway

Tue 10/11

11:27-08:30

2 stops28h 03m

$1,063

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 18/11

10:40-18:04

2 stops24h 24m

Chicago Midway

Wed 25/11

13:05-08:30

2 stops26h 25m

$1,063

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 5/4

09:15-08:49

2 stops38h 34m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,541

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 1/4

10:15-08:49

2 stops38h 34m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,541

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 31/3

10:15-08:49

2 stops38h 34m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,541

Flights are sorted by cheapest return flights first.

Deals found on 5/10

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 22 hours 59 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 $313, while return flights cost around $232.

  • How much is a return flight to Midway?

    A return flight to Midway will typically cost around $246, however they can be found for as little as $232.

  • 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 7 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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