$149+ 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 23/1. 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
8 Jan — 15 Jan1
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 9 December 2025.

Cheapest airline

Qantas Airways

Good one-way deal

$103 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago Midway (avg. price of $1,309).
Search Deals
Price to beat on a one-way flight from Chicago Midway.
Search Deals

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 9 December 2025.

Sun 24/514:00MDW - SYD
2 stops25h 35mDelta
Mon 8/609:25SYD - MDW
2 stops23h 40mDelta
Deal found 7/12$1,741
Wed 28/113:49MDW - BNE
2 stops26h 31mDelta
Sun 8/210:40BNE - MDW
2 stops27h 42mDelta
Deal found 8/12$1,752
Wed 29/414:00MDW - MEL
2 stops26h 40mDelta
Sun 31/510:00MEL - MDW
2 stops26h 45mDelta
Deal found 7/12$1,759
Sun 18/113:28MDW - SYD
2 stops24h 22mDelta
Sun 1/210:40SYD - MDW
2 stops28h 42mDelta
Deal found 7/12$1,759
Sun 18/118:14MDW - BNE
2 stops46h 06mDelta
Sun 1/210:40BNE - MDW
2 stops23h 56mDelta
Deal found 7/12$1,774
Sat 23/514:00MDW - SYD
2 stops25h 35mDelta
Mon 8/609:25SYD - MDW
2 stops23h 40mDelta
Deal found 7/12$1,816
Fri 27/209:34MDW - MEL
2 stops29h 26mDelta
Sun 8/310:10MEL - MDW
2 stops28h 19mDelta
Deal found 6/12$1,834
Wed 11/213:26MDW - SYD
2 stops26h 04mDelta
Fri 27/210:40SYD - MDW
2 stops29h 02mDelta
Deal found 7/12$1,834
Thu 25/1206:12MDW - SYD
2 stops32h 13mMultiple Airlines
Sun 18/111:20SYD - MDW
2 stops41h 27mMultiple Airlines
Deal found 7/12$1,868
Fri 13/210:53MDW - BNE
2 stops29h 27mDelta
Fri 20/210:40BNE - MDW
2 stops22h 57mDelta
Deal found 6/12$1,902
Fri 3/413:09MDW - MEL
2 stops27h 31mDelta
Fri 10/410:00MEL - MDW
2 stops27h 29mDelta
Deal found 8/12$1,910
Sat 31/113:26MDW - SYD
2 stops24h 24mDelta
Thu 12/210:40SYD - MDW
2 stops23h 57mDelta
Deal found 7/12$1,910

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 9 December 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

Mon 25/5

14:00-06:35

2 stops25h 35m

Sydney Kingsford Smith

Mon 8/6

09:25-18:05

2 stops23h 40m

$1,741

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 27/5

13:05-06:35

2 stops26h 30m

Sydney Kingsford Smith

Mon 8/6

09:25-18:05

2 stops23h 40m

$1,741

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Wed 28/1

13:26-08:20

2 stops26h 54m

Brisbane

Sun 8/2

10:40-22:22

2 stops27h 42m

$1,752

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 29/4

14:00-07:40

2 stops26h 40m

Melbourne

Sun 31/5

10:00-21:45

2 stops26h 45m

$1,759

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 18/1

13:28-06:50

2 stops24h 22m

Sydney Kingsford Smith

Wed 4/2

10:40-17:29

2 stops23h 49m

$1,759

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 15/3

09:30-06:05

2 stops28h 35m

Sydney Kingsford Smith

Wed 25/3

09:40-16:53

2 stops23h 13m

$1,759

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 15/2

13:28-08:30

2 stops26h 02m

Sydney Kingsford Smith

Tue 24/2

10:40-17:37

2 stops23h 57m

$1,759

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 8/2

11:45-06:50

2 stops26h 05m

Sydney Kingsford Smith

Tue 10/3

13:15-22:29

2 stops25h 14m

$1,759

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 19/1

09:32-08:30

2 stops29h 58m

Sydney Kingsford Smith

Mon 2/2

10:40-17:29

2 stops23h 49m

$1,759

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 10/2

13:51-08:30

2 stops25h 39m

Sydney Kingsford Smith

Tue 3/3

10:40-17:45

2 stops24h 05m

$1,759

Flights are sorted by cheapest return flights first.

Deals found on 7/12

Showing 1-10 of 39 results
1
2
3
4

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 (198 flights per day), Atlanta (193 flights per day) and Orlando (164 flights per day).

Toronto
Toronto
From $103

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 $103. Explore other affordable destinations below.

Toronto
Toronto
From $103

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 9 December 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 9 December 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, Miami. 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 $103 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for $103 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.

See more FAQs

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.

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.