$179+ 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 8/1. 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
14 Dec — 21 Dec1
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 14 November 2025.

Cheapest airline

Qantas Airways

Good one-way deal

$104 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago Midway (avg. price of $1,326).
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Price to beat on a one-way flight from Chicago Midway.
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Find flights from Midway

Enter your travel dates to find the best prices.

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 14 November 2025.

Fri 5/1206:15MDW - SYD
2 stops32h 10mMultiple Airlines
Tue 9/1211:20SYD - MDW
2 stops38h 26mMultiple Airlines
Deal found 11/11$1,669
Sun 1/206:20MDW - SYD
2 stops32h 05mMultiple Airlines
Thu 12/211:20SYD - MDW
2 stops29h 05mMultiple Airlines
Deal found 12/11$1,885
Thu 12/206:00MDW - SYD
2 stops32h 25mMultiple Airlines
Fri 27/211:20SYD - MDW
2 stops29h 05mMultiple Airlines
Deal found 12/11$2,042
Wed 29/410:35MDW - MEL
2 stops30h 05mDelta
Sun 31/510:00MEL - MDW
2 stops23h 31mDelta
Deal found 13/11$2,237
Sun 1/213:28MDW - SYD
2 stops24h 22mDelta
Sun 15/210:40SYD - MDW
2 stops22h 36mDelta
Deal found 12/11$2,237
Sun 18/119:16MDW - MEL
2 stops43h 44mDelta
Fri 26/610:00MEL - MDW
2 stops26h 45mDelta
Deal found 13/11$2,313
Wed 11/210:46MDW - SYD
2 stops28h 44mDelta
Fri 27/210:40SYD - MDW
2 stops24h 05mDelta
Deal found 13/11$2,313
Fri 16/113:28MDW - MEL
2 stops25h 32mDelta
Fri 26/610:00MEL - MDW
2 stops23h 31mDelta
Deal found 13/11$2,390
Thu 1/111:48MDW - SYD
2 stops27h 42mDelta
Sat 31/114:15SYD - MDW
2 stops25h 11mDelta
Deal found 12/11$2,390
Tue 23/1217:59MDW - MEL
2 stops45h 01mDelta
Sun 4/110:10MEL - MDW
2 stops29h 12mDelta
Deal found 13/11$2,466
Wed 24/1215:29MDW - SYD
2 stops24h 01mDelta
Mon 12/110:40SYD - MDW
2 stops28h 29mDelta
Deal found 12/11$2,466
Thu 25/1209:50MDW - SYD
2 stops28h 00mDelta
Mon 12/110:40SYD - MDW
2 stops22h 51mDelta
Deal found 13/11$2,542

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 14 November 2025. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Sydney

Route

Depart

Return

Price

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 1/2

06:20-07:25

2 stops32h 05m

Sydney Kingsford Smith

Thu 12/2

11:20-23:25

2 stops29h 05m

$1,885

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Sun 18/1

17:31-08:00

2 stops45h 29m

Melbourne

Sun 28/6

10:00-21:45

2 stops26h 45m

$2,237

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Sun 18/1

19:16-08:00

2 stops43h 44m

Melbourne

Fri 26/6

10:00-21:45

2 stops26h 45m

$2,313

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 11/2

10:46-08:30

2 stops28h 44m

Sydney Kingsford Smith

Fri 27/2

10:40-17:45

2 stops24h 05m

$2,313

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 11/2

13:28-08:30

2 stops26h 02m

Sydney Kingsford Smith

Thu 26/2

14:15-22:44

2 stops25h 29m

$2,313

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Fri 16/1

13:28-08:00

2 stops25h 32m

Melbourne

Fri 26/6

10:00-18:31

2 stops23h 31m

$2,390

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Fri 30/1

13:49-08:30

2 stops25h 41m

Sydney Kingsford Smith

Fri 13/2

10:40-17:45

2 stops24h 05m

$2,390

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 31/1

13:28-08:30

2 stops26h 02m

Sydney Kingsford Smith

Sat 14/2

14:15-22:44

2 stops25h 29m

$2,390

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 4/4

13:00-06:35

2 stops26h 35m

Sydney Kingsford Smith

Sat 25/4

09:25-18:31

2 stops24h 06m

$2,390

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 24/12

09:50-08:00

2 stops29h 10m

Melbourne

Sun 11/1

10:10-18:32

2 stops25h 22m

$2,466

Flights are sorted by cheapest return flights first.

Deals found on 12/11

Showing 1-10 of 58 results
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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 Atlanta (177 flights per day), Detroit (156 flights per day) and Orlando (138 flights per day).

Toronto
Toronto
From $104

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 $104. Explore other affordable destinations below.

Toronto
Toronto
From $104

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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 14 November 2025.
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 14 November 2025.

  • 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 Atlanta, Orlando Airport, Dallas/Fort Worth Airport. Atlanta, Las Vegas, Cancún 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 $104 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for $104 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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