$228+ Cheap flights from Chicago Midway Airport

This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — SYD
27 Apr — 4 May1
1 adult
1 adult, Economy, 0 bags

Find flights from Midway within your budget

 
Find flights departing from Midway that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 28 March 2026. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Route

Depart

Return

Price

Cheapest return flight
Fastest return journey

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 14/5

13:22-06:50

2 stops26h 28m

Sydney Kingsford Smith

Wed 27/5

09:15-17:56

2 stops23h 41m

$2,197

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 20/4

09:14-07:05

2 stops30h 51m

Sydney Kingsford Smith

Thu 14/5

17:50-15:57

2 stops37h 07m

$2,303

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 20/5

12:53-07:50

2 stops27h 57m

Melbourne

Sun 31/5

10:00-21:09

2 stops26h 09m

$2,340

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Fri 22/5

12:53-07:50

2 stops27h 57m

Melbourne

Sun 7/6

10:00-18:31

2 stops23h 31m

$2,340

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 2/9

13:05-07:50

2 stops27h 45m

Melbourne

Wed 9/9

10:00-18:31

2 stops23h 31m

$2,340

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Mon 31/8

13:05-07:50

2 stops27h 45m

Melbourne

Wed 9/9

10:00-18:31

2 stops23h 31m

$2,340

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 1/9

13:00-06:50

2 stops26h 50m

Sydney Kingsford Smith

Tue 8/9

09:15-18:31

2 stops24h 16m

$2,340

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Fri 18/9

13:00-06:50

2 stops26h 50m

Sydney Kingsford Smith

Sun 4/10

10:15-18:05

2 stops23h 50m

$2,340

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 26/8

09:30-06:50

2 stops30h 20m

Sydney Kingsford Smith

Tue 8/9

09:15-18:05

2 stops23h 50m

$2,340

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Thu 20/8

18:45-07:50

2 stops46h 05m

Melbourne

Wed 2/9

10:00-18:31

2 stops23h 31m

$2,356

Flights are sorted by cheapest return flights first.

Deals found on 26/3

Showing 1-10 of 43 resultsSorted by cheapest first
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Best time to book a flight from Midway

Have a flexible travel schedule? Discover the best time to fly from Midway with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Midway

Get recent, data-driven insights about flights from Midway including ideal travel times, pricing trends, and more.

What are popular destinations to fly to from Chicago Midway Airport?

Chicago Midway Airport offers frequent flights to Detroit (176 flights per day), Atlanta (140 flights per day) and Orlando (110 flights per day).

Toronto
Toronto
From $99

What is the cheapest place to fly to from Chicago Midway Airport?

The cheapest city to fly to from Chicago Midway Airport is Toronto, with prices starting at $99. Explore other affordable destinations below.

Toronto
Toronto
From $99

Browse thousands of different options on Cheapflights for your next trip

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Alternate flight departure points to Midway

Consider leaving from one of these other departure points that are located a short distance from Midway. Flight origins were last updated on 28 March 2026.
Flights from St. Louis
Flights from O'Hare Intl
Flights from Evansville
Flights from Belleville
Flights from Bloomington
Flights from Peoria
Flights from Moline
Flights from Springfield

Related info for your journey

Access useful and relevant information related to your journey from Midway. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 28 March 2026.

  • What are the most popular destinations to fly to from Chicago Midway Airport?

    For the current month, the most popular flights from Chicago Midway Airport are Orlando Airport, Phoenix Sky Harbor Intl Airport, Las Vegas. Atlanta, Las Vegas, Orlando Airport are the most popular locations from Chicago Midway Airport year round.

  • What is the cheapest flight from Chicago Midway Airport to anywhere?

    Users have flown out of Chicago Midway Airport for as low as $99 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for $99 to fly from Chicago Midway Airport.

  • How does Cheapflights help users find flights from Midway?

    Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Midway. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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

    Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Midway for you. Better yet — we are completely free to use.

  • Can Cheapflights find flights from Midway with no change fees?

    Cheapflights does show flights with no change fees to all users. To see these options for flights from Midway, users can toggle the no change fees filter when performing a flight search.

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

    Of course! You can now track prices for flights from Midway and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Midway?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Midway. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Midway for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Midway with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Midway, users can toggle the no change fees filter when performing a flight search.

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

Of course! You can now track prices for flights from Midway and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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