$1,206+ Cheap flights to Midway

— MDW
23 Oct — 30 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 8/1010:30 -
2 stops29h 13m
Sat 24/1006:21 -
2 stops34h 19m
Deal found 19/9$1,937
Fri 9/1010:10 -
2 stops28h 12m
Sat 24/1006:21 -
2 stops32h 04m
Deal found 18/9$1,958
Tue 10/1110:40 -
2 stops24h 24m
Tue 17/1113:31 -
2 stops25h 59m
Deal found 18/9$2,449
Fri 4/1210:40 -
2 stops24h 21m
Sun 13/1209:37 -
2 stops29h 53m
Deal found 19/9$2,523
Sun 22/1110:40 -
2 stops22h 59m
Sat 28/1113:31 -
2 stops25h 59m
Deal found 19/9$2,731
Mon 2/1110:40 -
2 stops23h 07m
Mon 9/1113:05 -
2 stops26h 25m
Deal found 18/9$2,744
Tue 3/1110:40 -
2 stops23h 07m
Tue 10/1111:27 -
2 stops28h 03m
Deal found 19/9$2,748
Mon 19/1010:15 -
2 stops22h 32m
Mon 26/1013:27 -
2 stops25h 53m
Deal found 20/9$2,751
Wed 2/1210:40 -
2 stops23h 10m
Wed 13/109:30 -
2 stops30h 00m
Deal found 22/9$2,772
Thu 5/1110:40 -
2 stops23h 07m
Thu 12/1113:05 -
2 stops26h 25m
Deal found 23/9$2,820

Find flight deals to Midway Airport

Return from

$1,276

One-way from

$1,206

Popular in

May

Cheapest in

October

Average price

$1,774
2/11-9/11
  • 2/11-9/11
  • 6 total stops
  • 69h 18m total
  • Sydney to Chicago
Search Deals
3/11-31/12
  • 3/11-31/12
  • 3 total stops
  • 38h 22m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($156 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

Tue 3/11

14:00-11:22

3 stops38h 22m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,206

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 6/11

14:00-11:25

3 stops38h 25m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,262

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 30/11

09:00-11:33

3 stops43h 33m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,660

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 17/12

09:00-12:59

3 stops44h 59m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,850

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

$1,960

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 15/12

10:40-09:37

2 stops39h 57m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,960

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 19/12

10:40-11:01

2 stops41h 21m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$2,058

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sun 20/12

10:40-09:13

2 stops39h 33m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$2,058
Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 1/12

14:05-09:26

1 stop36h 21m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$2,109

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 10/11

10:40-18:04

2 stops24h 24m

Chicago Midway

Tue 17/11

13:31-08:30

2 stops25h 59m

$2,449

Flights are sorted by cheapest return flights first.

Deals found on 21/9

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 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 $152, while return flights cost around $368.

  • How much is a return flight to Midway?

    A return flight to Midway will typically cost around $382, however they can be found for as little as $368.

  • 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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