$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 1/11. 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
17 Oct — 24 Oct1
1 adult
1 adult, Economy

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 September 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 $1,402).
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Price to beat on a one-way flight from Chicago Midway.
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Find flights from Midway

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 September 2025.

Mon 27/1012:03MDW - SYD
2 stops28h 57mMultiple Airlines
Sun 9/1114:05SYD - MDW
2 stops24h 58mMultiple Airlines
Deal found 15/9$1,548
Mon 20/1009:44MDW - SYD
2 stops30h 21mMultiple Airlines
Sun 2/1114:05SYD - MDW
2 stops24h 58mMultiple Airlines
Deal found 15/9$1,606
Thu 30/1006:30MDW - SYD
2 stops34h 30mMultiple Airlines
Thu 6/1111:20SYD - MDW
2 stops41h 10mMultiple Airlines
Deal found 15/9$2,114
Thu 20/1105:30MDW - SYD
2 stops38h 30mMultiple Airlines
Fri 12/1214:05SYD - MDW
1 stop24h 23mMultiple Airlines
Deal found 13/9$2,156
Mon 23/210:35MDW - BNE
2 stops29h 45mDelta
Wed 11/310:05BNE - MDW
2 stops23h 03mDelta
Deal found 16/9$2,192
Mon 8/1212:50MDW - MEL
2 stops26h 10mDelta
Sun 21/1210:10MEL - MDW
2 stops24h 09mDelta
Deal found 15/9$2,198
Sun 16/1113:47MDW - SYD
2 stops25h 43mDelta
Tue 9/1210:40SYD - MDW
2 stops29h 52mDelta
Deal found 13/9$2,198
Sun 1/313:00MDW - SYD
2 stops26h 30mDelta
Mon 16/309:40SYD - MDW
2 stops24h 28mDelta
Deal found 16/9$2,200
Tue 24/217:59MDW - BNE
2 stops46h 21mDelta
Wed 11/310:05BNE - MDW
2 stops23h 03mDelta
Deal found 15/9$2,207
Sat 22/1119:02MDW - SYD
2 stops44h 28mDelta
Sun 7/1210:40SYD - MDW
2 stops29h 52mDelta
Deal found 13/9$2,225
Wed 11/213:00MDW - SYD
2 stops26h 30mDelta
Thu 26/210:40SYD - MDW
2 stops24h 54mDelta
Deal found 15/9$2,273
Wed 11/209:30MDW - SYD
2 stops30h 00mDelta
Fri 27/210:40SYD - MDW
2 stops24h 28mDelta
Deal found 16/9$2,274

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 September 2025. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Sydney

Route

Depart

Return

Price

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Mon 23/2

10:35-08:20

2 stops29h 45m

Brisbane

Wed 11/3

10:05-18:08

2 stops23h 03m

$2,192

ChicagoBrisbane

MDW - BNE

MDWBNE

Chicago Midway

Wed 25/2

09:20-08:20

2 stops31h 00m

Brisbane

Wed 11/3

10:05-18:34

2 stops23h 29m

$2,192

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Mon 16/2

09:20-08:00

2 stops29h 40m

Melbourne

Sun 1/3

10:10-18:08

2 stops24h 58m

$2,198

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Mon 8/12

12:50-08:00

2 stops26h 10m

Melbourne

Sun 21/12

10:10-17:19

2 stops24h 09m

$2,198

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Mon 2/2

13:00-08:00

2 stops26h 00m

Melbourne

Sun 15/2

10:10-21:46

2 stops28h 36m

$2,198

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Mon 19/1

09:30-08:00

2 stops29h 30m

Melbourne

Sun 1/2

10:10-18:08

2 stops24h 58m

$2,198

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 18/1

10:35-06:50

2 stops27h 15m

Sydney Kingsford Smith

Tue 27/1

14:15-21:46

2 stops24h 31m

$2,198

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 10/11

13:47-08:30

2 stops25h 43m

Sydney Kingsford Smith

Wed 26/11

10:40-18:08

2 stops24h 28m

$2,198

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 4/3

13:00-08:00

2 stops26h 00m

Melbourne

Sun 15/3

09:10-18:34

2 stops25h 24m

$2,200

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Mon 26/1

10:35-08:00

2 stops28h 25m

Melbourne

Sun 8/2

10:10-21:46

2 stops28h 36m

$2,200

Flights are sorted by cheapest return flights first.

Deals found on 14/9

Showing 1-10 of 51 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 Detroit (230 flights per day), Atlanta (149 flights per day) and Minneapolis (114 flights per day).

Toronto
Toronto
From $68

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 $68

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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 17 September 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 September 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 Las Vegas, Atlanta, Orlando Airport. 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.

  • 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 $2,047 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.

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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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