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C$ 97+ Cheap flights from Chicago Midway Airport

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/3. 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 — YTZ
7 Mar — 14 Mar1
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 5 February 2026.

Cheapest airline

WestJet

Good round-trip deal

C$ 494 or less

Good one-way deal

C$ 121 or less
On average, WestJet currently has the cheapest one-way flight from Chicago Midway (avg. price of C$ 305).
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Price to beat on a round-trip flight from Chicago Midway.
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Price to beat on a one-way flight from Chicago Midway.
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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 5 February 2026.

Thu 26/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sun 1/32:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 5/2C$ 248
Thu 19/34:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Wed 25/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/2C$ 250
Fri 27/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sat 28/211:05 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/2C$ 252
Sun 24/510:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Thu 28/54:00 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/2C$ 259
Tue 26/55:35 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Thu 28/54:00 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/2C$ 264
Thu 23/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Mon 27/46:45 a.m.
YUL
-
MDW
1 stop4h 20m
Porter Airlines
Deal found 2/2C$ 268
Fri 3/44:15 p.m.
MDW
-
YUL
1 stop5h 30m
Porter Airlines
Mon 6/46:45 a.m.
YUL
-
MDW
1 stop4h 20m
Porter Airlines
Deal found 3/2C$ 270
Tue 14/411:00 a.m.
MDW
-
YUL
1 stop6h 15m
Porter Airlines
Sat 18/48:55 a.m.
YUL
-
MDW
1 stop3h 55m
Porter Airlines
Deal found 2/2C$ 271
Fri 29/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Mon 8/61:00 p.m.
YUL
-
MDW
1 stop4h 50m
Porter Airlines
Deal found 2/2C$ 276
Thu 16/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Sun 19/48:55 a.m.
YUL
-
MDW
1 stop7h 25m
Porter Airlines
Deal found 4/2C$ 280
Wed 8/44:15 p.m.
MDW
-
YUL
1 stop5h 30m
Porter Airlines
Sun 12/48:55 a.m.
YUL
-
MDW
1 stop7h 25m
Porter Airlines
Deal found 5/2C$ 282
Thu 9/44:15 p.m.
MDW
-
YUL
1 stop5h 30m
Porter Airlines
Sun 12/48:55 a.m.
YUL
-
MDW
1 stop7h 25m
Porter Airlines
Deal found 4/2C$ 285

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 5 February 2026. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Toronto Island

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 26/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

Toronto Island

Sun 1/3

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

C$ 249

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 24/5

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Thu 28/5

4:00 p.m.-4:50 p.m.

Nonstop1h 50m

C$ 259

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 24/5

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Wed 27/5

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 259

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 26/5

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Wed 27/5

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 264

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 26/5

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Thu 28/5

4:00 p.m.-4:50 p.m.

Nonstop1h 50m

C$ 264

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 25/5

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Fri 29/5

4:00 p.m.-4:50 p.m.

Nonstop1h 50m

C$ 264

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 26/5

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Fri 29/5

4:00 p.m.-4:50 p.m.

Nonstop1h 50m

C$ 264

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 14/4

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

Toronto Island

Fri 24/4

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

C$ 267

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 7/5

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Mon 11/5

4:00 p.m.-4:50 p.m.

Nonstop1h 50m

C$ 270

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Tue 14/4

11:00 a.m.-4:30 p.m.

1 stop4h 30m

Montreal Pierre Elliott Trudeau Intl

Sun 19/4

8:55 a.m.-3:20 p.m.

1 stop7h 25m

C$ 293

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

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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 round-trip 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 is the cheapest month to book a flight from Chicago Midway Airport?

Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport (average of C$ 123). Flying from Chicago Midway Airport in November will prove the most costly (average of C$ 395). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

What are popular destinations to fly to from Chicago Midway Airport?

From Chicago Midway Airport you can expect to find greater availability for the following destinations: Detroit (176 flights per day), Atlanta (161 flights per day) and Orlando (88 flights per day).

New York
New York
From C$ 132
Toronto
Toronto
From C$ 104
Zacatecas La Calera
Zacatecas La Calera
From C$ 494
Buffalo
Buffalo
From C$ 121

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 C$ 104. Explore other affordable destinations below.

Toronto
Toronto
From C$ 104
Buffalo
Buffalo
From C$ 121
New York
New York
From C$ 132
Zacatecas La Calera
Zacatecas La Calera
From C$ 494

Browse thousands of different options on Cheapflights for your next trip

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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 5 February 2026.
Flights from St. Louis
Flights from O'Hare Intl
Flights from Evansville
Flights from Belleville
Flights from Bloomington
Flights from Peoria
Flights from Champaign
Flights from Moline
Flights from Dubuque
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 5 February 2026.

  • What are the most popular destinations to fly to from Chicago Midway Airport?

    This month, the top selected destinations from Chicago Midway Airport are Tampa, Atlanta, Las Vegas. Throughout the year, Atlanta, Las Vegas, Orlando Airport are some of the top choices made by users flying from Chicago Midway Airport.

  • What is the cheapest flight from Chicago Midway Airport to anywhere?

    Users have flown out of Chicago Midway Airport for as low as C$ 104 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for C$ 285 to fly from Chicago Midway Airport.

  • What is the cheapest month to fly from Chicago Midway Airport?

    At the present moment the cheapest month to fly from Chicago Midway Airport is currently March; with November being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.

  • Where are the cheapest places to fly to from Chicago Midway Airport?

    Check out the cheapest flights from Chicago Midway Airport to embark to:
    Travel from Chicago to Montreal from C$ 238 round trip
    Travel from Chicago to Toronto from C$ 249 round trip
    Travel from Chicago to Calgary from C$ 394 round trip
    Travel from Chicago to Vancouver from C$ 401 round trip

  • How does Cheapflights help users find flights from Midway?

    Deals for flights from Midway are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose to your preference, such as price, airport, cabin class, and plenty of other options.

  • Why should you use Cheapflights to find cheap flight tickets from Midway?

    Cheapflights helps you find that perfect flight from Midway by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

  • Can Cheapflights find flights from Midway with no change fees?

    Yes! Cheapflights helps users easily find flights from Midway with no change fees.

  • Can Cheapflights notify me if prices for flights from Midway become cheaper?

    Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Midway?

Deals for flights from Midway are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose to your preference, such as price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Midway?

Cheapflights helps you find that perfect flight from Midway by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Midway with no change fees?

Yes! Cheapflights helps users easily find flights from Midway with no change fees.

Can Cheapflights notify me if prices for flights from Midway become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

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