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C$ 93+ 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 14/2. 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
15 Feb — 22 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 16 January 2026.

Cheapest airline

WestJet

Good round-trip deal

C$ 478 or less

Good one-way deal

C$ 123 or less
On average, WestJet currently has the cheapest one-way flight from Chicago Midway (avg. price of C$ 273).
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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 16 January 2026.

Fri 6/211:05 a.m.
MDW
-
YUL
1 stop5h 40m
Porter Airlines
Sun 8/210:15 a.m.
YUL
-
MDW
1 stop6h 05m
Porter Airlines
Deal found 14/1C$ 267
Wed 11/211:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Tue 17/29:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 13/1C$ 275
Wed 18/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Tue 10/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 14/1C$ 278
Thu 29/111:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Tue 3/29:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 14/1C$ 282
Tue 17/34:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Mon 30/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 14/1C$ 284
Fri 6/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Mon 9/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 13/1C$ 285
Sat 14/212:50 p.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Wed 18/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 15/1C$ 286
Fri 20/34:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sat 28/311:00 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 14/1C$ 288
Tue 17/34:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Tue 31/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 14/1C$ 289
Wed 28/111:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sat 31/111:00 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 14/1C$ 290
Sat 28/312:45 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Tue 31/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 14/1C$ 292
Thu 19/34:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Tue 31/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 14/1C$ 293

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 16 January 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

Wed 11/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Sun 15/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 275

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 11/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Tue 17/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 275

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 18/2

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

Nonstop1h 42m

Toronto Island

Tue 10/3

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 278

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 19/2

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

Nonstop1h 42m

Toronto Island

Sun 22/2

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

Nonstop1h 50m

C$ 279

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 6/2

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

Nonstop1h 42m

Toronto Island

Mon 9/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

C$ 282

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 29/1

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

Nonstop1h 42m

Toronto Island

Tue 3/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 282

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 17/3

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

Nonstop1h 42m

Toronto Island

Mon 30/3

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 284

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 29/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Mon 2/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 284

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 3/3

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Mon 9/3

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 288

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 18/3

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Sat 28/3

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

C$ 288

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/1

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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$ 110). Flying from Chicago Midway Airport in November will prove the most costly (average of C$ 402). 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 (150 flights per day), Atlanta (120 flights per day) and Orlando (106 flights per day).

New York
New York
From C$ 135
Toronto
Toronto
From C$ 477
Zacatecas La Calera
Zacatecas La Calera
From C$ 502
Buffalo
Buffalo
From C$ 123

What is the cheapest place to fly to from Chicago Midway Airport?

The cheapest city to fly to from Chicago Midway Airport is Buffalo, with prices starting at C$ 123. Explore other affordable destinations below.

Buffalo
Buffalo
From C$ 123
New York
New York
From C$ 135
Toronto
Toronto
From C$ 477
Zacatecas La Calera
Zacatecas La Calera
From C$ 502

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 16 January 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 16 January 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 Cancún, Atlanta, Miami. 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$ 123 to Buffalo (prices may vary depending on the airline and departure time). On average, users have booked flights for C$ 357 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$ 236 round trip
    Travel from Chicago to Toronto from C$ 243 round trip
    Travel from Chicago to Calgary from C$ 340 round trip
    Travel from Chicago to Vancouver from C$ 374 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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