$203+ 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 14/12. 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
25 Dec — 1 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 25 November 2025.

Cheapest airline

Qantas Airways

Good one-way deal

$105 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago Midway (avg. price of $1,345).
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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 25 November 2025.

Sun 18/113:28MDW - SYD
2 stops26h 02mDelta
Sun 1/210:40SYD - MDW
2 stops28h 42mDelta
Deal found 24/11$1,782
Mon 23/213:49MDW - BNE
2 stops26h 31mDelta
Wed 11/310:05BNE - MDW
2 stops23h 35mDelta
Deal found 23/11$1,796
Wed 29/410:35MDW - MEL
2 stops30h 05mDelta
Sun 31/510:00MEL - MDW
2 stops23h 31mDelta
Deal found 23/11$1,804
Tue 10/210:48MDW - SYD
2 stops27h 02mDelta
Tue 3/310:40SYD - MDW
2 stops24h 05mDelta
Deal found 24/11$1,804
Sun 15/217:00MDW - BNE
2 stops47h 20mDelta
Wed 4/311:05BNE - MDW
2 stops22h 32mDelta
Deal found 24/11$1,819
Wed 11/310:49MDW - MEL
2 stops28h 11mDelta
Fri 20/309:10MEL - MDW
2 stops25h 30mDelta
Deal found 23/11$1,881
Wed 11/213:26MDW - SYD
2 stops26h 04mDelta
Fri 27/210:40SYD - MDW
2 stops23h 57mDelta
Deal found 24/11$1,881
Fri 6/310:53MDW - MEL
2 stops28h 07mDelta
Fri 13/309:10MEL - MDW
2 stops25h 30mDelta
Deal found 24/11$1,958
Fri 23/110:48MDW - SYD
2 stops28h 42mDelta
Fri 30/110:40SYD - MDW
2 stops24h 56mDelta
Deal found 23/11$1,958
Sat 7/308:00MDW - MEL
2 stops35h 25mMultiple Airlines
Fri 13/316:05MEL - MDW
1 stop37h 54mMultiple Airlines
Deal found 24/11$2,130
Thu 15/109:50MDW - SYD
2 stops28h 00mDelta
Sun 25/110:40SYD - MDW
2 stops28h 42mDelta
Deal found 23/11$2,299
Fri 16/113:49MDW - SYD
2 stops25h 41mDelta
Fri 23/110:40SYD - MDW
2 stops23h 49mDelta
Deal found 23/11$2,377

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 25 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 18/1

13:28-08:30

2 stops26h 02m

Sydney Kingsford Smith

Sun 1/2

10:40-22:22

2 stops28h 42m

$1,782

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Mon 23/2

13:49-08:20

2 stops26h 31m

Brisbane

Wed 11/3

10:05-18:40

2 stops23h 35m

$1,796

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Mon 23/3

09:32-07:00

2 stops29h 28m

Melbourne

Wed 8/4

10:00-22:29

2 stops27h 29m

$1,804

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 29/4

10:35-07:40

2 stops30h 05m

Melbourne

Sun 31/5

10:00-18:31

2 stops23h 31m

$1,804

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 25/3

13:09-07:00

2 stops25h 51m

Melbourne

Wed 8/4

10:00-22:29

2 stops27h 29m

$1,804

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 8/2

11:45-08:30

2 stops27h 45m

Sydney Kingsford Smith

Tue 10/3

09:40-16:53

2 stops23h 13m

$1,804

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 10/2

13:26-08:30

2 stops26h 04m

Sydney Kingsford Smith

Tue 3/3

14:15-22:44

2 stops25h 29m

$1,804

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 10/2

13:26-06:50

2 stops24h 24m

Sydney Kingsford Smith

Tue 17/2

14:15-22:44

2 stops25h 29m

$1,804

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Sun 15/2

17:00-08:20

2 stops47h 20m

Brisbane

Wed 4/3

11:05-17:37

2 stops22h 32m

$1,819

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 11/3

10:49-07:00

2 stops28h 11m

Melbourne

Fri 20/3

09:10-18:40

2 stops25h 30m

$1,881

Flights are sorted by cheapest return flights first.

Deals found on 24/11

Showing 1-10 of 39 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 (141 flights per day), Detroit (124 flights per day) and Orlando (112 flights per day).

Toronto
Toronto
From $105

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 $105. Explore other affordable destinations below.

Toronto
Toronto
From $105

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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 25 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 25 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, Denver. 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 $105 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for $105 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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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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