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C$ 84+ 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 18/2. 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 — YVR
28 Feb — 7 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 29 January 2026.

Cheapest airline

WestJet

Good round-trip deal

C$ 465 or less

Good one-way deal

C$ 120 or less
On average, WestJet currently has the cheapest one-way flight from Chicago Midway (avg. price of C$ 302).
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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 29 January 2026.

Fri 3/44:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Mon 6/49:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/1C$ 254
Thu 19/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sat 21/211:05 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/1C$ 260
Sat 4/412:45 p.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Sat 11/411:00 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 27/1C$ 262
Thu 7/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Sun 10/512:25 p.m.
YUL
-
MDW
1 stop5h 25m
Porter Airlines
Deal found 27/1C$ 264
Tue 17/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Thu 19/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/1C$ 264
Sat 11/412:45 p.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Sun 12/49:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 27/1C$ 265
Thu 16/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sun 19/49:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/1C$ 266
Mon 9/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Thu 12/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 28/1C$ 269
Wed 11/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sun 10/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/1C$ 270
Tue 19/55:35 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sun 24/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/1C$ 272
Wed 11/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Tue 12/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/1C$ 273
Sat 28/212:50 p.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Sat 7/311:00 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 29/1C$ 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 29 January 2026. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Vancouver Intl

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 8/5

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

Nonstop1h 40m

Toronto Island

Sun 10/5

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

Nonstop1h 50m

C$ 260

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 27/2

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$ 266

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 29/5

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

Nonstop1h 40m

Toronto Island

Sun 31/5

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

Nonstop1h 50m

C$ 266

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$ 266

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 8/5

5:35 p.m.-8:15 p.m.

Nonstop1h 40m

Toronto Island

Mon 11/5

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

Nonstop1h 50m

C$ 266

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 16/4

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

Nonstop1h 42m

Toronto Island

Sun 19/4

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

Nonstop1h 50m

C$ 266

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 20/3

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

Nonstop1h 42m

Toronto Island

Wed 25/3

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

Nonstop1h 50m

C$ 268

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 28/2

12:50 p.m.-3:32 p.m.

Nonstop1h 42m

Toronto Island

Sat 7/3

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

Nonstop1h 50m

C$ 274

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 16/3

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

Nonstop1h 42m

Toronto Island

Thu 19/3

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

Nonstop1h 50m

C$ 276

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 11/4

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

Toronto Island

Sat 18/4

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

Nonstop1h 50m

C$ 276

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/1

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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 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 (178 flights per day), Atlanta (176 flights per day) and Orlando (80 flights per day).

Toronto
Toronto
From C$ 86
New York
New York
From C$ 131
Zacatecas La Calera
Zacatecas La Calera
From C$ 488
Buffalo
Buffalo
From C$ 120

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$ 86. Explore other affordable destinations below.

Toronto
Toronto
From C$ 86
Buffalo
Buffalo
From C$ 120
New York
New York
From C$ 131
Zacatecas La Calera
Zacatecas La Calera
From C$ 488

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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 29 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 29 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$ 86 to Toronto Island Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for C$ 304 to fly from Chicago Midway Airport.

  • 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$ 231 round trip
    Travel from Chicago to Toronto from C$ 235 round trip
    Travel from Chicago to Vancouver from C$ 316 round trip
    Travel from Chicago to Calgary from C$ 404 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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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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