Midway

$180+ Cheap flights from Canada to Midway (MDW)

YYZ — MDW
Dec 6 — Dec 131
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1. Tell us where you want to go

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Cheap flight deals from Canada to Midway

Cheapest flights from Canada to Midway

Fri 11/206:00 am -
1 stop7h 51m
Mon 11/231:31 pm -
1 stop8h 56m
Deal found 11/1$324
Wed 11/256:00 am -
1 stop4h 46m
Sun 11/299:30 am -
1 stop3h 00m
Deal found 11/1$326
Thu 11/266:00 am -
1 stop6h 25m
Sun 11/291:31 pm -
1 stop8h 26m
Deal found 11/1$329
Tue 12/16:00 am -
1 stop8h 01m
Tue 12/85:12 pm -
1 stop5h 36m
Deal found 11/1$335
Wed 12/26:00 am -
1 stop8h 01m
Mon 12/71:02 pm -
1 stop9h 46m
Deal found 11/1$337
Thu 12/36:00 am -
1 stop4h 37m
Mon 12/76:41 pm -
1 stop3h 52m
Deal found 11/4$342
Wed 12/26:00 am -
1 stop4h 37m
Tue 12/85:12 pm -
1 stop5h 36m
Deal found 11/3$344
Thu 11/266:00 am -
1 stop6h 25m
Sun 11/296:00 am -
1 stop10h 27m
Deal found 11/2$345
Sat 11/218:45 am -
1 stop7h 54m
Sat 11/2812:30 pm -
1 stop9h 28m
Deal found 11/2$348
Thu 12/36:00 am -
1 stop8h 01m
Mon 12/76:41 pm -
1 stop3h 52m
Deal found 11/5$352
Wed 12/169:45 am -
1 stop4h 16m
Thu 1/71:59 pm -
1 stop8h 00m
Deal found 11/4$353
Wed 12/28:45 am -
1 stop8h 05m
Sat 12/512:39 pm -
1 stop9h 28m
Deal found 11/5$355

Find flight deals from Canada to Midway

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$304
(Delta)

One-way from

$180
(Delta)

Popular in

October

Cheapest in

February

Average price

$288

Good round-trip deal

$214 or less

Good one-way deal

$247 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
From Canada to Chicago Midway
One-way flight from Canada to Chicago Midway
Highest demand for flights based on searches. 2% potential increase in price ($8 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Average for round-trip flights in November 2026
Price to beat on a round-trip flight from Canada to Chicago Midway.
Price to beat on a one-way flight from Canada to Chicago Midway.

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Canada to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 1/9

6:10 am-9:16 am

1 stop4h 06m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$194

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 12/17

12:15 pm-6:01 pm

1 stop6h 46m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$194

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 1/11

6:10 am-1:17 pm

1 stop8h 07m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$194

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 12/1

6:00 am-9:37 am

1 stop4h 37m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$194

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 1/19

12:10 pm-6:00 pm

1 stop6h 50m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$195

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 1/17

6:10 am-9:16 am

1 stop4h 06m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$195

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 1/10

6:10 am-9:16 am

1 stop4h 06m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$195

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 12/16

6:00 am-9:37 am

1 stop4h 37m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$198

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 11/15

6:00 am-12:51 pm

1 stop7h 51m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$198

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 12/15

6:00 am-9:37 am

1 stop4h 37m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Canada to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Canada with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Canada to Chicago Midway Airport

What is the cheapest month to book a flight from Canada to Chicago Midway Airport?

Currently, January is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of $204). Flying from Canada to Chicago Midway Airport in October is currently the most expensive (average of $504). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How often are flights from Canada to Chicago delayed?

About 16% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 107 minutes.

What is the most punctual flight time for Canada to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Canada to Chicago flights?

Over the last year, Porter Airlines have had the lowest number of delays on this route, with just 16% of flights being delayed.

Reviews of airlines servicing Midway

Read through reviews of airlines operating flights from Canada to Chicago Midway Airport, such as Porter Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

6.9

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Entertainment

6.9

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

  • How long is the flight from Canada to Chicago Midway Airport?

    Airlines like Delta and WestJet fly from Canada to Chicago Midway Airport in about 13h 53m. The time it takes to get you to your destination can typically vary by up to 1h 17m. The distance from Canada to Chicago Midway Airport is about 722 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Canada to Chicago Midway Airport?

  • Can I find deals for flights from Canada to Midway that include hotel bookings?

    Yes. In addition to deals on Canada to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Canada to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Canada to Midway.

  • Can I find deals for business class flights from Canada to Midway?

    Yes. Cheapflights offers flight deals from Canada to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Canada to Chicago Midway Airport?

    Currently, January is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of $204). Flying from Canada to Chicago Midway Airport in October is currently the most expensive (average of $504). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Canada to Midway

Top airline flying from Canada to Midway

AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$185Average$365FlexibilityNo cancel feeOn-time52%

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