$145+ 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 17/4. 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
5 Apr — 12 Apr1
1 adult
1 adult, Economy, 0 bags

What to know about flights from Midway

Discover essential information about flights departing from Midway, including flight schedules, destinations, airlines operating at the Midway airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 6 March 2026.

Cheapest airline

Qantas Airways

Good one-way deal

$97 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago Midway (avg. price of $2,181).
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Price to beat on a one-way flight from Chicago Midway.
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Find flights from Midway

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Cheapest flights from Midway
Explore the most affordable flight options available from Midway. Find the lowest fares based on data from user searches, with prices last updated on 6 March 2026.

Thu 16/416:15
MDW
-
SYD
2 stops28h 35m
Multiple Airlines
Thu 23/412:00
SYD
-
MDW
1 stop25h 22m
Multiple Airlines
Deal found 1/3$1,954
Wed 27/521:11
MDW
-
SYD
2 stops47h 39m
Multiple Airlines
Mon 1/612:00
SYD
-
MDW
1 stop23h 06m
Multiple Airlines
Deal found 5/3$1,968
Thu 14/516:09
MDW
-
SYD
2 stops28h 41m
Multiple Airlines
Wed 27/512:00
SYD
-
MDW
1 stop23h 06m
Multiple Airlines
Deal found 6/3$2,043
Wed 20/513:22
MDW
-
MEL
2 stops27h 28m
Delta
Sun 31/510:00
MEL
-
MDW
2 stops23h 33m
Delta
Deal found 2/3$2,085
Sun 26/412:52
MDW
-
SYD
2 stops26h 58m
Delta
Sun 10/509:15
SYD
-
MDW
2 stops23h 41m
Delta
Deal found 2/3$2,085
Wed 18/311:19
MDW
-
SYD
2 stops28h 06m
Multiple Airlines
Thu 23/409:10
SYD
-
MDW
2 stops47h 44m
Multiple Airlines
Deal found 3/3$2,139
Wed 5/813:05
MDW
-
SYD
2 stops26h 45m
Delta
Sun 30/809:15
SYD
-
MDW
2 stops24h 16m
Delta
Deal found 4/3$2,154
Wed 29/412:52
MDW
-
MEL
2 stops27h 58m
Delta
Sun 31/510:00
MEL
-
MDW
2 stops23h 33m
Delta
Deal found 3/3$2,156
Mon 30/314:05
MDW
-
SYD
2 stops25h 45m
Delta
Sat 18/409:15
SYD
-
MDW
2 stops28h 13m
Delta
Deal found 2/3$2,156
Wed 1/412:47
MDW
-
MEL
2 stops28h 03m
Delta
Wed 8/410:00
MEL
-
MDW
2 stops37h 53m
Delta
Deal found 4/3$2,170
Fri 17/414:12
MDW
-
MEL
2 stops26h 38m
Delta
Fri 24/410:00
MEL
-
MDW
2 stops27h 28m
Delta
Deal found 5/3$2,297
Wed 15/714:00
MDW
-
MEL
2 stops26h 50m
Delta
Fri 31/710:00
MEL
-
MDW
2 stops26h 45m
Delta
Deal found 2/3$2,334

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 6 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

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 20/5

13:22-07:50

2 stops27h 28m

Melbourne

Sun 31/5

10:00-18:33

2 stops23h 33m

$2,085

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Tue 7/4

18:07-07:50

2 stops46h 43m

Melbourne

Wed 22/4

10:00-22:28

2 stops27h 28m

$2,085

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 6/4

10:45-06:50

2 stops29h 05m

Sydney Kingsford Smith

Mon 20/4

09:15-17:58

2 stops23h 43m

$2,085
Fastest return journey

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 29/6

14:00-06:50

2 stops25h 50m

Sydney Kingsford Smith

Mon 13/7

09:15-18:31

2 stops24h 16m

$2,085

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 29/4

12:52-07:50

2 stops27h 58m

Melbourne

Sun 31/5

10:00-21:09

2 stops26h 09m

$2,154

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 1/6

09:23-06:50

2 stops30h 27m

Sydney Kingsford Smith

Mon 15/6

09:15-18:05

2 stops23h 50m

$2,154

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 16/8

13:05-06:50

2 stops26h 45m

Sydney Kingsford Smith

Thu 3/9

09:15-18:05

2 stops23h 50m

$2,156

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 19/8

14:00-06:50

2 stops25h 50m

Sydney Kingsford Smith

Tue 1/9

09:15-18:31

2 stops24h 16m

$2,156

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 22/8

14:00-06:50

2 stops25h 50m

Sydney Kingsford Smith

Sat 5/9

09:15-21:46

2 stops27h 31m

$2,226

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 2/4

14:05-07:50

2 stops25h 45m

Sydney Kingsford Smith

Thu 16/4

09:15-18:36

2 stops24h 21m

$2,297

Flights are sorted by cheapest return flights first.

Deals found on 3/3

Showing 1-10 of 45 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 (96 flights per day), Atlanta (75 flights per day) and Minneapolis (42 flights per day).

Toronto
Toronto
From $97

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 $97. Explore other affordable destinations below.

Toronto
Toronto
From $97

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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 6 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 6 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, Las Vegas, Phoenix Sky Harbor Intl Airport. 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 $97 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for $97 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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