$171+ 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 13/1. 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
23 Nov — 30 Nov1
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 24 October 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 $1,372).
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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 24 October 2025.

Wed 11/209:20MDW - MEL
2 stops29h 40mDelta
Wed 25/210:10MEL - MDW
2 stops24h 58mDelta
Deal found 22/10$2,252
Tue 30/1211:48MDW - SYD
2 stops26h 02mDelta
Tue 20/114:15SYD - MDW
2 stops24h 31mDelta
Deal found 23/10$2,252
Sat 21/318:45MDW - MEL
2 stops68h 15mDelta
Sun 5/410:00MEL - MDW
2 stops38h 56mDelta
Deal found 21/10$2,280
Fri 12/1206:00MDW - MEL
2 stops33h 00mDelta
Sun 11/110:10MEL - MDW
2 stops28h 36mDelta
Deal found 22/10$2,329
Wed 31/1206:00MDW - SYD
2 stops33h 30mDelta
Fri 30/110:40SYD - MDW
2 stops28h 06mDelta
Deal found 22/10$2,329
Thu 11/1210:36MDW - MEL
2 stops52h 24mDelta
Wed 14/110:10MEL - MDW
2 stops24h 58mDelta
Deal found 22/10$2,361
Wed 31/1206:00MDW - SYD
2 stops33h 30mDelta
Wed 21/110:40SYD - MDW
2 stops24h 54mDelta
Deal found 23/10$2,367
Thu 1/109:29MDW - SYD
2 stops30h 01mDelta
Sat 10/110:40SYD - MDW
2 stops24h 54mDelta
Deal found 22/10$2,406
Wed 10/1213:14MDW - SYD
2 stops26h 16mDelta
Sat 10/114:15SYD - MDW
2 stops35h 39mDelta
Deal found 21/10$2,444
Wed 10/1210:36MDW - MEL
2 stops28h 24mDelta
Wed 14/110:10MEL - MDW
2 stops28h 36mDelta
Deal found 22/10$2,483
Mon 29/1211:48MDW - SYD
2 stops27h 42mDelta
Mon 19/110:40SYD - MDW
2 stops24h 28mDelta
Deal found 23/10$2,483
Tue 9/1213:14MDW - SYD
2 stops26h 16mDelta
Fri 19/1210:40SYD - MDW
2 stops30h 07mDelta
Deal found 21/10$2,560

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

Fly to

Sydney

Route

Depart

Return

Price

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 11/2

09:20-08:00

2 stops29h 40m

Melbourne

Wed 25/2

10:10-18:08

2 stops24h 58m

$2,252

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 29/12

17:59-06:50

2 stops43h 51m

Sydney Kingsford Smith

Sun 18/1

10:40-18:08

2 stops24h 28m

$2,252

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 30/12

09:29-06:50

2 stops28h 21m

Sydney Kingsford Smith

Wed 21/1

10:40-18:08

2 stops24h 28m

$2,252

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 30/12

09:50-06:50

2 stops28h 00m

Sydney Kingsford Smith

Mon 19/1

10:40-18:08

2 stops24h 28m

$2,252

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 30/12

11:48-06:50

2 stops26h 02m

Sydney Kingsford Smith

Tue 20/1

14:15-21:46

2 stops24h 31m

$2,252

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Sat 21/3

18:45-07:00

2 stops68h 15m

Melbourne

Sun 5/4

10:00-09:56

2 stops38h 56m

$2,280

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Tue 20/1

17:25-08:00

2 stops45h 35m

Melbourne

Fri 30/1

10:10-21:46

2 stops28h 36m

$2,329

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Fri 12/12

06:00-08:00

2 stops33h 00m

Melbourne

Sun 11/1

10:10-21:46

2 stops28h 36m

$2,329

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Fri 12/12

06:00-08:00

2 stops33h 00m

Melbourne

Wed 14/1

10:10-08:50

2 stops39h 40m

$2,329

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 2/4

09:20-07:35

2 stops30h 15m

Sydney Kingsford Smith

Sun 12/4

09:25-18:34

2 stops24h 09m

$2,329

Flights are sorted by cheapest return flights first.

Deals found on 23/10

Showing 1-10 of 60 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 (160 flights per day), Atlanta (131 flights per day) and Orlando (108 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 24 October 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 24 October 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, Las Vegas, Dallas/Fort Worth 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 $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.

  • 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 $1,619 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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