$148+ 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 29/1. 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
16 Jan — 23 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 17 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 $1,308).
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 17 December 2025.

Wed 28/113:26MDW - BNE
2 stops26h 54mDelta
Sun 8/210:40BNE - MDW
2 stops27h 42mDelta
Deal found 16/12$1,752
Wed 11/313:09MDW - MEL
2 stops25h 51mDelta
Sun 22/309:10MEL - MDW
2 stops29h 19mDelta
Deal found 16/12$1,760
Tue 10/213:26MDW - SYD
2 stops24h 24mDelta
Tue 17/214:15SYD - MDW
2 stops25h 29mDelta
Deal found 15/12$1,760
Tue 10/219:16MDW - BNE
2 stops45h 04mDelta
Sun 22/210:40BNE - MDW
2 stops23h 05mDelta
Deal found 15/12$1,774
Sun 18/119:16MDW - BNE
2 stops45h 04mDelta
Wed 28/111:05BNE - MDW
2 stops22h 24mDelta
Deal found 15/12$1,777
Thu 12/318:35MDW - MEL
2 stops44h 25mDelta
Sun 22/309:10MEL - MDW
2 stops25h 30mDelta
Deal found 15/12$1,835
Wed 11/209:33MDW - SYD
2 stops29h 57mDelta
Thu 26/210:40SYD - MDW
2 stops24h 05mDelta
Deal found 15/12$1,835
Sun 1/209:33MDW - SYD
2 stops29h 57mDelta
Sun 22/210:40SYD - MDW
2 stops29h 02mDelta
Deal found 15/12$1,909
Sat 14/313:09MDW - SYD
2 stops24h 56mDelta
Fri 3/410:15SYD - MDW
2 stops23h 40mDelta
Deal found 16/12$1,911
Thu 5/209:53MDW - SYD
2 stops29h 37mDelta
Sun 22/210:40SYD - MDW
2 stops29h 02mDelta
Deal found 14/12$1,984
Thu 5/315:00MDW - MEL
2 stops28h 25mMultiple Airlines
Sat 14/316:05MEL - MDW
1 stop20h 11mMultiple Airlines
Deal found 15/12$2,586
Fri 26/1209:50MDW - MEL
2 stops29h 10mDelta
Wed 21/110:10MEL - MDW
2 stops24h 19mDelta
Deal found 15/12$2,739

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 17 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

Sun 1/2

13:26-06:50

2 stops24h 24m

Sydney Kingsford Smith

Sun 15/2

10:40-22:42

2 stops29h 02m

$1,745

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Wed 28/1

13:49-08:20

2 stops26h 31m

Brisbane

Wed 4/2

11:05-22:22

2 stops27h 17m

$1,752

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Wed 28/1

12:48-08:20

2 stops27h 32m

Brisbane

Sun 8/2

10:40-22:22

2 stops27h 42m

$1,752

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 11/3

13:09-07:00

2 stops25h 51m

Melbourne

Sun 22/3

09:10-22:29

2 stops29h 19m

$1,760

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Sun 1/2

18:14-08:00

2 stops44h 46m

Melbourne

Sun 22/2

10:10-22:42

2 stops29h 32m

$1,760

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 29/4

13:00-07:50

2 stops27h 50m

Melbourne

Sun 31/5

10:00-21:45

2 stops26h 45m

$1,760

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 9/2

13:51-08:30

2 stops25h 39m

Sydney Kingsford Smith

Mon 16/2

10:40-17:45

2 stops24h 05m

$1,760

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 28/1

13:26-08:30

2 stops26h 04m

Sydney Kingsford Smith

Mon 9/2

10:40-17:29

2 stops23h 49m

$1,760

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 1/2

12:48-08:30

2 stops26h 42m

Sydney Kingsford Smith

Wed 18/2

10:40-17:37

2 stops23h 57m

$1,760

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 31/3

12:47-07:35

2 stops26h 48m

Sydney Kingsford Smith

Wed 15/4

09:15-18:05

2 stops23h 50m

$1,760

Flights are sorted by cheapest return flights first.

Deals found on 16/12

Showing 1-10 of 45 results
1
2
3
...
5

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 (164 flights per day), Atlanta (145 flights per day) and Orlando (120 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 17 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 17 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.

  • Where are the cheapest places to fly to from Chicago Midway Airport?

    View the cheapest flight destinations from Chicago Midway Airport:
    Fly from Chicago to Sydney from $1,606 round trip

  • 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.