$177+ 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 8/12. 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
7 Dec — 14 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 7 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 $1,337).
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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 7 November 2025.

Mon 26/106:00MDW - SYD
2 stops32h 25mMultiple Airlines
Mon 2/211:20SYD - MDW
2 stops29h 05mMultiple Airlines
Deal found 4/11$1,762
Mon 1/1213:15MDW - SYD
2 stops26h 15mDelta
Mon 8/1210:40SYD - MDW
2 stops22h 54mDelta
Deal found 5/11$1,951
Sun 19/414:00MDW - SYD
2 stops25h 35mDelta
Sat 2/509:25SYD - MDW
2 stops24h 06mDelta
Deal found 4/11$2,028
Thu 4/1213:14MDW - SYD
2 stops26h 16mDelta
Thu 11/1210:40SYD - MDW
2 stops22h 38mDelta
Deal found 4/11$2,105
Wed 29/413:00MDW - MEL
2 stops27h 40mDelta
Sun 31/510:00MEL - MDW
2 stops23h 31mDelta
Deal found 6/11$2,254
Tue 20/106:00MDW - SYD
2 stops33h 30mDelta
Mon 2/210:40SYD - MDW
2 stops23h 52mDelta
Deal found 6/11$2,254
Wed 18/212:46MDW - SYD
2 stops26h 44mDelta
Mon 2/310:40SYD - MDW
2 stops24h 05mDelta
Deal found 5/11$2,256
Sun 1/219:16MDW - BNE
2 stops45h 04mDelta
Sun 22/210:40BNE - MDW
2 stops23h 05mDelta
Deal found 6/11$2,264
Sun 1/319:17MDW - BNE
2 stops45h 03mDelta
Sun 15/309:40BNE - MDW
2 stops23h 54mDelta
Deal found 6/11$2,285
Thu 20/1106:05MDW - SYD
2 stops33h 55mMultiple Airlines
Thu 27/1111:20SYD - MDW
2 stops28h 23mMultiple Airlines
Deal found 7/11$2,301
Wed 11/212:48MDW - SYD
2 stops26h 42mDelta
Thu 26/210:40SYD - MDW
2 stops24h 57mDelta
Deal found 6/11$2,331
Sat 31/113:28MDW - SYD
2 stops26h 02mDelta
Sun 8/210:40SYD - MDW
2 stops28h 46mDelta
Deal found 5/11$2,333

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 7 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

Mon 1/12

13:15-08:30

2 stops26h 15m

Sydney Kingsford Smith

Mon 8/12

10:40-16:34

2 stops22h 54m

$1,951

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 19/4

14:00-06:35

2 stops25h 35m

Sydney Kingsford Smith

Sat 2/5

09:25-18:31

2 stops24h 06m

$2,028

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 29/4

13:00-07:40

2 stops27h 40m

Melbourne

Sun 31/5

10:00-18:31

2 stops23h 31m

$2,254

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 20/1

06:00-08:30

2 stops33h 30m

Sydney Kingsford Smith

Mon 2/2

10:40-17:32

2 stops23h 52m

$2,254

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 8/3

09:30-06:05

2 stops28h 35m

Sydney Kingsford Smith

Sun 22/3

09:40-18:34

2 stops24h 54m

$2,256

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 22/4

14:00-06:35

2 stops25h 35m

Sydney Kingsford Smith

Tue 5/5

09:25-21:45

2 stops27h 20m

$2,256

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Sun 1/2

19:16-08:20

2 stops45h 04m

Brisbane

Sun 22/2

10:40-17:45

2 stops23h 05m

$2,264

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Sun 1/3

19:17-08:20

2 stops45h 03m

Brisbane

Sun 15/3

09:40-18:34

2 stops23h 54m

$2,285

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 20/11

06:05-09:00

2 stops33h 55m

Sydney Kingsford Smith

Thu 27/11

11:20-22:43

2 stops28h 23m

$2,301

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 11/2

12:48-08:30

2 stops26h 42m

Sydney Kingsford Smith

Thu 26/2

10:40-18:37

2 stops24h 57m

$2,331

Flights are sorted by cheapest return flights first.

Deals found on 5/11

Showing 1-10 of 46 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 Orlando (148 flights per day), Detroit (110 flights per day) and Atlanta (94 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 7 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 7 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, Las Vegas. 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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