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

According to our data, Porter Airlines has had the least delays on this route over the last 12 months, with about 14% of their flights experiencing any sort of delay.

How often are flights from Chicago to Canada delayed?

Historically, on average around 15% of flights between Chicago and Canada have experienced a delay on any given week. The average delay length over the past 12 months has been 118 minutes.

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

Thursday is statistically the day of the week that experiences the fewest delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

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

Generally, flights departing in the morning tend to experience fewer delays. Flights departing at night have, in the past, seen delays more frequently in comparison.

What is the cheapest airline that flies from Chicago Midway to Canada?

Porter Airlines, Delta, and Air Transat are the most popular carriers operating from Chicago Midway to Canada

How many flights depart from Chicago Midway Airport to Canada on average per week?

4 flights are operational weekly from Chicago Midway Airport to Canada as of February 2026. The most popular departure day for this route is Thu, with 50% of flights per week taking off on this day.

When did momondo last update prices for flights from Chicago Midway Airport to Canada?

Prices for flights from Chicago Midway Airport to Canada were last updated today.

How old do you have to be to fly from Chicago Midway Airport to Canada?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Canada.

What documentation or ID do you need to fly to Canada?

The necessary travel and health documents for your Canada trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

C$ 96 Cheap Flights from Chicago Midway Airport to Canada in 2026

1 adult

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago Midway Airport to Canada

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

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

MDW

YTZ

1h 42mdirect

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

YTZ

MDW

1h 50mdirect

C$ 234Porter Airlines

Sat, 4 Apr - Sun, 5 Apr

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

MDW

YTZ

1h 42mdirect

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

YTZ

MDW

1h 50mdirect

C$ 238Porter Airlines

Thu, 26 Mar - Sun, 29 Mar

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

MDW

YTZ

1h 40mdirect

1:45 p.m. - 2:35 p.m.

YTZ

MDW

1h 50mdirect

C$ 239Porter Airlines

Mon, 15 Jun - Thu, 25 Jun

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

MDW

YTZ

1h 42mdirect

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

YTZ

MDW

1h 50mdirect

C$ 241Porter Airlines

Thu, 26 Mar - Mon, 30 Mar

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

MDW

YTZ

1h 40mdirect

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

YTZ

MDW

1h 50mdirect

C$ 242Porter Airlines

Fri, 8 May - Mon, 11 May

9:35 a.m. - 5:17 p.m.

MDW

YYZ

6h 42m

1 stop

10:05 a.m. - 12:29 p.m.

YYZ

MDW

3h 24m

1 stop

C$ 339Delta

Thu, 2 Apr - Sun, 12 Apr

9:35 a.m. - 5:17 p.m.

MDW

YYZ

6h 42m

1 stop

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

YYZ

MDW

7h 09m

1 stop

C$ 347Delta

Wed, 18 Mar - Sun, 22 Mar

2:15 p.m. - 7:09 p.m.

MDW

YYC

29h 54m

1 stop

9:00 p.m. - 7:31 p.m.

YYC

MDW

21h 31m

2 stops

C$ 384Multiple Airlines

Thu, 16 Apr - Mon, 27 Apr

7:30 a.m. - 11:35 a.m.

MDW

YYZ

27h 05m

1 stop

6:20 p.m. - 1:02 p.m.

YYZ

MDW

19h 42m

1 stop

C$ 391Multiple Airlines

Thu, 12 Mar - Mon, 16 Mar

9:35 a.m. - 12:21 a.m.

MDW

YYJ

16h 46m

3 stops

3:00 p.m. - 12:29 p.m.

YYJ

MDW

19h 29m

3 stops

C$ 1,026WestJet

Thu, 19 Mar - Mon, 23 Mar

Delta flights from Chicago Midway Airport to Canada

Our best Delta deals on Chicago Midway Airport to Canada flight tickets

Delta

17 Apr

MDW1:24 p.m.Chicago Midway

8h 55m

1 stop

YUL11:19 p.m.Montreal Pierre Elliott Trudeau Intl

21 Apr

YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl

7h 32m

1 stop

MDW1:32 p.m.Chicago Midway

C$ 324

Delta

25 May

MDW6:23 a.m.Chicago Midway

10h 19m

1 stop

YUL5:42 p.m.Montreal Pierre Elliott Trudeau Intl

5 Jun

YUL12:40 p.m.Montreal Pierre Elliott Trudeau Intl

9h 29m

1 stop

MDW9:09 p.m.Chicago Midway

C$ 326

Delta

9 Apr

MDW6:34 p.m.Chicago Midway

3h 39m

1 stop

YUL11:13 p.m.Montreal Pierre Elliott Trudeau Intl

12 Apr

YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl

7h 24m

1 stop

MDW1:24 p.m.Chicago Midway

C$ 328

WestJet flights from Chicago Midway Airport to Canada

Our best WestJet deals on Chicago Midway Airport to Canada flight tickets

WestJet

4 Apr

MDW1:10 p.m.Chicago Midway

3h 07m

1 stop

YYZ5:17 p.m.Toronto Pearson Intl

7 Apr

YYZ6:20 a.m.Toronto Pearson Intl

3h 33m

1 stop

MDW8:53 a.m.Chicago Midway

C$ 469

WestJet

27 Mar

MDW9:30 a.m.Chicago Midway

12h 36m

1 stop

YYZ11:06 p.m.Toronto Pearson Intl

1 Apr

YYZ10:05 a.m.Toronto Pearson Intl

3h 24m

1 stop

MDW12:29 p.m.Chicago Midway

C$ 471

WestJet

25 Mar

MDW9:30 a.m.Chicago Midway

13h 08m

2 stops

YYZ11:38 p.m.Toronto Pearson Intl

26 Mar

YYZ6:10 p.m.Toronto Pearson Intl

16h 46m

1 stop

MDW9:56 a.m.Chicago Midway

C$ 472

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 4/4

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

Nonstop1h 42m

Toronto Island

Sun 5/4

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

Nonstop1h 50m

C$ 234

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 26/3

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

Nonstop1h 42m

Toronto Island

Sun 29/3

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

Nonstop1h 50m

C$ 238

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 15/6

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

Nonstop1h 40m

Toronto Island

Thu 25/6

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 239

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 26/3

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

Nonstop1h 42m

Toronto Island

Mon 30/3

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

Nonstop1h 50m

C$ 241

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 8/5

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

Nonstop1h 40m

Toronto Island

Mon 11/5

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

Nonstop1h 50m

C$ 242

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 2/4

9:35 a.m.-5:17 p.m.

1 stop6h 42m

Toronto Pearson Intl

Sun 12/4

10:05 a.m.-12:29 p.m.

1 stop3h 24m

C$ 339

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 18/3

9:35 a.m.-5:17 p.m.

1 stop6h 42m

Toronto Pearson Intl

Sun 22/3

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

1 stop7h 09m

C$ 347

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 16/4

2:15 p.m.-7:09 p.m.

1 stop29h 54m

Calgary

Mon 27/4

9:00 p.m.-7:31 p.m.

2 stops21h 31m

C$ 384

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 12/3

7:30 a.m.-11:35 a.m.

1 stop27h 05m

Toronto Pearson Intl

Mon 16/3

6:20 p.m.-1:02 p.m.

1 stop19h 42m

C$ 391

ChicagoVictoria

MDW - YYJ

MDWYYJ

Chicago Midway

Thu 19/3

9:35 a.m.-12:21 a.m.

3 stops16h 46m

Victoria Intl

Mon 23/3

3:00 p.m.-12:29 p.m.

3 stops19h 29m

C$ 1,026

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Canada

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the cheapest month to fly to Canada?

In general, July is the cheapest month to fly from Chicago Midway Airport to Canada. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 245. If you’re not able to fly to Canada in July, then January is your next best option. Flight prices from Chicago Midway Airport to Canada during January average around C$ 256.

What is the cheapest day to depart on your flight to Canada?

Our data shows that Tuesday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as C$ 303. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 431. These prices are subject to change though, so be sure to set up a Price Alert for flights to Canada.

What is the cheapest time of day to depart on your flight to Canada?

According to our data, the cheapest time of day to fly to Canada is in the morning. momondo users have found flights departing from Chicago Midway Airport to Canada in the morning for as low as C$ 338. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the afternoon is when there is more demand to fly to Canada, so prices are often more expensive at around C$ 344 per ticket.

What is the cheapest Chicago Midway to Canada flight route?

Fly from Chicago Midway to Toronto Island for the best Chicago Midway - Canada flight prices

What cabin class options are available on Chicago Midway to Canada flights?

There is only 1 cabin class available to choose from on Chicago Midway to Canada flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Canada flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Canada.

Cheap Chicago Midway Airport to Canada flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Canada

Best price found	C$ 183
Fastest flight time	1h 40m
Direct flights	Every day
Airports in Canada	513 airports

The best one-way flight to Canada from Chicago Midway Airport in the past 72 hours is C$ 183. The best round-trip flight deal from Chicago Midway Airport to Canada found on momondo in the last 72 hours is C$ 250.

The fastest flight from Chicago Midway Airport to Canada takes 1h 40m

Direct flights go from Chicago Midway Airport to Canada every day.

There are 513 airports in Canada. From Chicago Midway Airport there are direct flights to Toronto Island (YTZ).

Search flight deals

When did momondo last update prices for flights from Chicago Midway Airport to Canada?
Prices for flights from Chicago Midway Airport to Canada were last updated today.
How old do you have to be to fly from Chicago Midway Airport to Canada?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Canada.
What documentation or ID do you need to fly to Canada?
The necessary travel and health documents for your Canada trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Canada?
Based on momondo bookings for flights between Chicago Midway Airport and Canada, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 31.34% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 20.30%, Embraer 170 with 19.97%, and Embraer 175 with 11.63%.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Canada?

It is quick and easy to find Chicago to Canada flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Canada that suits you.

Can I find flights from Chicago to Canada with flexible booking policies on momondo?

All flight searches from Chicago to Canada on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Canada?

Once all potential Chicago to Canada flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Canada right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Canada flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Canada trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Sun 29/3

Sun 5/4

Email me momondo's favourite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Canada

Popular cities

Other flights from Chicago Midway Airport

Other flights to Canada

Airlines

Cabin classes

Complete your trip

Feeling lucky

Popular Cities in Canada

Flights to Torontofrom C$ 48

Flights to Vancouverfrom C$ 67

Flights to Montrealfrom C$ 100

Flights to Calgaryfrom C$ 90

Flights to Ottawafrom C$ 127

Flights to Winnipegfrom C$ 123

Flights to Halifaxfrom C$ 82

Flights to Kelownafrom C$ 89

Flights to Saskatoonfrom C$ 160

Flights to Reginafrom C$ 127

Flights to St. John'sfrom C$ 150

Flights to Québec Cityfrom C$ 275

Cheap flights from Chicago Midway Airport to Canada from C$ 96

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Canada departing on 26/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago Midway Airport to Canada

Cheap round-trip flights

Cheap one-way flights

Cheap last-minute flights

Cheap direct flights

Delta flights from Chicago Midway Airport to Canada

Our best Delta deals on Chicago Midway Airport to Canada flight tickets

WestJet flights from Chicago Midway Airport to Canada

Our best WestJet deals on Chicago Midway Airport to Canada flight tickets

momondo Fare Finder

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

See travel insights to Canada from

How to get the cheapest flight ticket from Chicago Midway Airport to Canada

What is the cheapest month to fly to Canada?

What is the cheapest day to depart on your flight to Canada?

What is the cheapest time of day to depart on your flight to Canada?

What is the cheapest Chicago Midway to Canada flight route?

What cabin class options are available on Chicago Midway to Canada flights?

Can stopping save me money on Chicago Midway Airport to Canada flights?

What is the cheapest airline that flies from Chicago Midway to Canada?

How often are flights from Chicago to Canada delayed?

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

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

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

How many flights depart from Chicago Midway Airport to Canada on average per week?

Cheap Chicago Midway Airport to Canada flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Canada

Best price found

Fastest flight time

Direct flights

Airports in Canada

Why use momondo?

An easier way to manage your Canada trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Canada

Popular Cities in Canada

Popular flights according to clicks in the last 7 days on momondo

Chicago Midway Airport flight routes

According to popular flight searches on momondo this year

Canada flight routes

According to popular flight searches on momondo this year

Fly your favourite airline to Canada

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Canada

List of cabin classes available on flights landing in Canada. Availability may vary depending on flight origin and airline.

Complete your trip to Canada

Explore popular destinations other users love

According to popular flight searches on momondo this year