$215+ 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 20/1. 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
30 Jan — 6 Feb1
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 31 December 2025.

Cheapest airline

Qantas Airways

Good one-way deal

$102 or less
On average, Qantas Airways currently has the cheapest one-way flight from Chicago Midway (avg. price of $1,295).
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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 31 December 2025.

Mon 9/209:45MDW - SYD
2 stops28h 40mMultiple Airlines
Wed 18/211:20SYD - MDW
2 stops41h 07mMultiple Airlines
Deal found 30/12$1,710
Wed 28/113:26MDW - BNE
2 stops26h 54mDelta
Sun 8/210:40BNE - MDW
2 stops27h 42mDelta
Deal found 28/12$1,737
Wed 28/113:26MDW - SYD
2 stops26h 04mDelta
Wed 4/210:40SYD - MDW
2 stops28h 42mDelta
Deal found 30/12$1,744
Mon 30/313:10MDW - SYD
2 stops26h 25mDelta
Sat 18/409:15SYD - MDW
2 stops23h 39mDelta
Deal found 30/12$1,819
Sun 1/207:30MDW - SYD
2 stops32h 30mMultiple Airlines
Sun 8/211:20SYD - MDW
2 stops27h 59mMultiple Airlines
Deal found 30/12$1,868
Thu 29/113:49MDW - SYD
2 stops25h 41mDelta
Thu 5/210:40SYD - MDW
2 stops23h 49mDelta
Deal found 30/12$1,893
Sun 22/206:00MDW - SYD
2 stops34h 00mMultiple Airlines
Tue 10/311:20SYD - MDW
2 stops46h 53mMultiple Airlines
Deal found 30/12$2,053
Sat 28/213:28MDW - SYD
2 stops26h 02mDelta
Fri 6/310:40SYD - MDW
2 stops24h 05mDelta
Deal found 30/12$2,132
Wed 11/312:47MDW - MEL
2 stops26h 13mDelta
Sun 22/309:10MEL - MDW
2 stops24h 44mDelta
Deal found 29/12$2,192
Mon 29/614:00MDW - SYD
2 stops25h 35mDelta
Mon 13/709:15SYD - MDW
2 stops24h 16mDelta
Deal found 29/12$2,192
Sat 28/209:15MDW - SYD
2 stops29h 10mMultiple Airlines
Sat 7/311:20SYD - MDW
2 stops28h 21mMultiple Airlines
Deal found 30/12$2,241
Fri 8/513:05MDW - MEL
2 stops27h 45mDelta
Sun 17/510:00MEL - MDW
2 stops23h 31mDelta
Deal found 29/12$2,266

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 31 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 9/2

09:45-07:25

2 stops28h 40m

Sydney Kingsford Smith

Wed 18/2

11:20-11:27

2 stops41h 07m

$1,710

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Wed 11/2

13:26-08:20

2 stops26h 54m

Brisbane

Wed 18/2

11:05-17:37

2 stops22h 32m

$1,737

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

$1,737

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 9/2

13:51-08:30

2 stops25h 39m

Sydney Kingsford Smith

Mon 16/2

10:40-17:37

2 stops23h 57m

$1,744

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 1/2

12:46-06:50

2 stops25h 04m

Sydney Kingsford Smith

Sun 8/2

10:40-22:22

2 stops28h 42m

$1,744

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 22/2

13:28-06:50

2 stops24h 22m

Sydney Kingsford Smith

Tue 10/3

09:40-18:40

2 stops25h 00m

$1,744

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 28/1

13:26-08:30

2 stops26h 04m

Sydney Kingsford Smith

Wed 4/2

10:40-22:22

2 stops28h 42m

$1,744

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 26/5

13:00-06:35

2 stops26h 35m

Sydney Kingsford Smith

Wed 10/6

09:15-18:31

2 stops24h 16m

$1,744

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 29/1

13:49-08:30

2 stops25h 41m

Sydney Kingsford Smith

Thu 5/2

10:40-17:29

2 stops23h 49m

$1,893

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Fri 1/5

12:55-06:35

2 stops26h 40m

Sydney Kingsford Smith

Fri 8/5

09:15-18:05

2 stops23h 50m

$1,893

Flights are sorted by cheapest return flights first.

Deals found on 30/12

Showing 1-10 of 49 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 (150 flights per day), Detroit (124 flights per day) and Orlando (106 flights per day).

Toronto
Toronto
From $102

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 $102. Explore other affordable destinations below.

Toronto
Toronto
From $102

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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 31 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 31 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 $102 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for $102 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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