$132+ 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 23/5. 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
11 May — 18 May1
1 adult
1 adult, Economy, 0 bags

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 11 April 2026. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Mon 3/8

11:05-07:50

2 stops29h 45m

Melbourne

Wed 12/8

10:00-18:31

2 stops23h 31m

$2,276

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 1/6

10:59-06:50

2 stops28h 51m

Sydney Kingsford Smith

Mon 15/6

09:15-18:18

2 stops24h 03m

$2,276

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 29/6

12:45-06:50

2 stops27h 05m

Sydney Kingsford Smith

Mon 13/7

09:15-18:18

2 stops24h 03m

$2,276

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 29/7

13:16-06:50

2 stops26h 34m

Sydney Kingsford Smith

Tue 11/8

09:15-18:05

2 stops23h 50m

$2,276

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 13/7

09:49-06:50

2 stops30h 01m

Sydney Kingsford Smith

Wed 29/7

09:15-22:15

2 stops28h 00m

$2,276

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 16/8

13:05-06:50

2 stops26h 45m

Sydney Kingsford Smith

Wed 26/8

09:15-18:05

2 stops23h 50m

$2,278

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 1/9

13:05-06:50

2 stops26h 45m

Sydney Kingsford Smith

Thu 10/9

09:15-18:05

2 stops23h 50m

$2,278
Fastest return journey

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 23/9

14:00-07:50

2 stops26h 50m

Melbourne

Fri 2/10

10:00-18:31

2 stops23h 31m

$2,281

ChicagoMelbourne

MDW - MEL

MDWMEL

Chicago Midway

Wed 23/9

13:00-07:50

2 stops27h 50m

Melbourne

Sun 4/10

11:00-18:31

2 stops23h 31m

$2,281

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 22/9

13:05-06:50

2 stops26h 45m

Sydney Kingsford Smith

Sat 3/10

09:15-18:05

2 stops23h 50m

$2,281

Flights are sorted by cheapest return flights first.

Deals found on 8/4

Showing 1-10 of 42 resultsSorted by cheapest first
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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 (220 flights per day), Atlanta (162 flights per day) and Minneapolis (94 flights per day).

Toronto
Toronto
From $96

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 $96. Explore other affordable destinations below.

Toronto
Toronto
From $96

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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 11 April 2026.
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 11 April 2026.

  • 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 Los Angeles, Atlanta, Las Vegas. Atlanta, Las Vegas, Orlando Airport 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 $96 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for $96 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 $1,520 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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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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