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C$ 87+ 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 24/4. 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
5 Apr — 12 Apr1
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 6 March 2026.

Cheapest airline

United Airlines

Good round-trip deal

C$ 257 or less

Good one-way deal

C$ 128 or less
On average, United Airlines currently has the cheapest one-way flight from Chicago Midway (avg. price of C$ 362).
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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 6 March 2026.

Thu 26/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Mon 30/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/3C$ 234
Thu 16/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Wed 22/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 2/3C$ 237
Thu 2/44:05 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sun 5/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/3C$ 240
Fri 10/44:05 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sun 12/42:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 5/3C$ 241
Fri 10/44:05 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Mon 13/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/3C$ 243
Wed 1/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Wed 8/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 4/3C$ 245
Sat 28/312:45 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Mon 30/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 5/3C$ 247
Thu 9/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sat 11/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/3C$ 249
Thu 16/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sun 19/42:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 3/3C$ 251
Fri 1/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Fri 29/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Deal found 1/3C$ 256
Sun 3/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Thu 28/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Deal found 1/3C$ 258
Fri 29/510:25 a.m.
MDW
-
YUL
1 stop6h 50m
Porter Airlines
Tue 2/66:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Deal found 1/3C$ 264

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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 26/3

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

Nonstop1h 42m

Toronto Island

Sun 5/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

C$ 241
Quickest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 8/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Sun 10/5

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

Nonstop1h 50m

C$ 282

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 15/4

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

Nonstop1h 42m

Toronto Island

Sun 19/4

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

Nonstop1h 50m

C$ 284

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 25/4

12:55 p.m.-3:37 p.m.

Nonstop1h 42m

Toronto Island

Tue 28/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

C$ 290

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 24/4

4:05 p.m.-6:47 p.m.

Nonstop1h 42m

Toronto Island

Sun 26/4

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

Nonstop1h 50m

C$ 296

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 5/6

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Sun 7/6

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

Nonstop1h 50m

C$ 318

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 19/4

4:05 p.m.-6:47 p.m.

Nonstop1h 42m

Toronto Island

Sun 26/4

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

Nonstop1h 50m

C$ 320

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Mon 25/5

3:20 p.m.-8:10 p.m.

1 stop3h 50m

Montreal Pierre Elliott Trudeau Intl

Fri 5/6

6:30 a.m.-9:40 a.m.

1 stop4h 10m

C$ 324

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 8/5

6:36 p.m.-10:59 p.m.

1 stop3h 23m

Toronto Pearson Intl

Mon 11/5

4:04 p.m.-6:33 p.m.

1 stop3h 29m

C$ 338

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 3/4

9:35 a.m.-3:08 p.m.

1 stop4h 33m

Toronto Pearson Intl

Sun 5/4

6:20 a.m.-12:29 p.m.

1 stop7h 09m

C$ 338

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 60 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 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$ 106). Flying from Chicago Midway Airport in November will prove the most costly (average of C$ 394). 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 (96 flights per day), Atlanta (75 flights per day) and Minneapolis (42 flights per day).

Toronto
Toronto
From C$ 103
New York
New York
From C$ 132
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From C$ 67

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

The cheapest city to fly to from Chicago Midway Airport is Atlanta Hartsfield-Jackson, with prices starting at C$ 67. Explore other affordable destinations below.

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From C$ 67
Toronto
Toronto
From C$ 103
New York
New York
From C$ 132

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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 6 March 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 6 March 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 Orlando Airport, Las Vegas, Phoenix Sky Harbor Intl Airport. 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$ 67 to Atlanta (prices may vary depending on the airline and departure time). On average, users have booked flights for C$ 198 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$ 237 round trip
    Travel from Chicago to Calgary from C$ 386 round trip
    Travel from Chicago to Vancouver from C$ 440 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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