$1,235+ Cheap flights to Midway

— MDW
1 Nov — 8 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

Tue 10/1110:40 -
2 stops24h 24m
Tue 17/1113:31 -
2 stops25h 59m
Deal found 1/10$2,757
Thu 12/1110:40 -
2 stops22h 59m
Mon 30/1112:30 -
2 stops27h 00m
Deal found 27/9$2,782
Thu 29/1009:40 -
2 stops23h 07m
Thu 5/1112:27 -
2 stops27h 03m
Deal found 1/10$2,834
Fri 30/1009:40 -
2 stops24h 20m
Sat 7/1113:27 -
2 stops26h 03m
Deal found 30/9$2,920
Mon 5/1010:15 -
2 stops24h 04m
Mon 19/1012:49 -
2 stops27h 01m
Deal found 30/9$2,922
Tue 20/1010:15 -
2 stops22h 32m
Tue 27/1012:49 -
2 stops26h 31m
Deal found 28/9$2,932
Mon 5/1010:15 -
2 stops24h 04m
Tue 13/1012:27 -
2 stops27h 23m
Deal found 28/9$2,933
Sun 4/1010:15 -
2 stops24h 18m
Tue 13/1012:27 -
2 stops27h 23m
Deal found 30/9$2,996
Thu 1/1009:15 -
2 stops24h 18m
Fri 9/1013:27 -
2 stops26h 23m
Deal found 29/9$3,007
Thu 8/1010:15 -
2 stops22h 32m
Sat 24/1012:27 -
2 stops26h 53m
Deal found 28/9$3,009
Fri 23/1010:15 -
2 stops22h 32m
Thu 29/1012:49 -
2 stops26h 31m
Deal found 2/10$3,048
Tue 20/1021:45 -
2 stops54h 32m
Tue 27/1012:27 -
1 stop26h 28m
Deal found 28/9$3,289

Find flight deals to Midway Airport

Return from

$1,059

One-way from

$1,235

Popular in

May

Cheapest in

October

Average price

$1,487
American Airlines
  • American Airlines
  • 5/11-9/11
  • 3 total stops
  • 46h 20m total
  • Sydney to Chicago
Search Deals
5/12-31/12
  • 5/12-31/12
  • 3 total stops
  • 49h 55m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($155 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 20/11

06:25-13:33

3 stops48h 08m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,307

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 14/11

21:30-23:47

2 stops43h 17m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,359

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 3/12

10:40-08:55

2 stops39h 15m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,562

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sun 29/11

21:40-11:33

3 stops54h 53m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,603
Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 20/11

10:40-16:39

2 stops22h 59m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,662

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sun 6/12

10:40-18:01

2 stops48h 21m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,668

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 8/12

10:40-16:50

2 stops23h 10m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,685

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 12/11

10:40-18:04

2 stops24h 24m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$1,760

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 5/12

10:40-16:50

2 stops23h 10m

Chicago Midway

Wed 31/12

00:00-16:00

Nonstop0h 00m

$2,073

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

$2,757

Flights are sorted by cheapest return flights first.

Deals found on 27/9

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 24 hours 24 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 $156, while return flights cost around $378.

  • How much is a return flight to Midway?

    A return flight to Midway will typically cost around $391, however they can be found for as little as $378.

  • 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 0 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

Browse thousands of different options on Cheapflights for your next trip

Search flights to Midway by cabin class

First Class flights to Chicago Midway Airport
Business Class flights to Chicago Midway Airport
Prem Economy Class flights to Chicago Midway Airport
Economy Class flights to Chicago Midway Airport

Fly with Cheapflights

How does Cheapflights help users find flights to Midway?

Cheapflights helps you search for flights to Midway via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets to Midway?

Cheapflights simply makes it quick and affordable to book flights to Midway by bringing together all flight options from hundreds of airlines and agencies online — and we put them in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights to Midway with no change fees?

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.

Can Cheapflights notify me if prices for flights to Midway become cheaper?

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.