How often are flights from Canada to Chicago delayed?

Historically, on average around 15% of flights between Canada and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 108 minutes.

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

As of February 2026, there are 1 flights per day flying from Canada to Chicago Midway Airport. The most common time of day flights depart is 9:00a.m., with 100% of flights taking off at noon.

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

Tuesday 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.

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

As of February 2026, 10 flights take off from Canada and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.

Which airline has the best punctuality record on Canada to Chicago 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.

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

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

How long does it take to fly to Chicago Midway Airport?

Flight times from Canada to Chicago Midway Airport vary, but if you’re flying out of Toronto and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 1h 55m on average. Another popular route from Canada to Chicago Midway Airport is flying from Montreal to Chicago O'Hare Intl Airport, which will take roughly 2h 35m. Keep in mind that layovers or delays could extend your travel time.

What is the most punctual flight time for Canada to Chicago 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.

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

Prices for flights from Canada to Chicago Midway Airport are updated daily.

How many operators does momondo search for flights from Canada to Chicago Midway Airport?

As of February 2026, there is 1 operator available to choose from for flights from Canada to Chicago Midway Airport.

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

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 Canada to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

C$ 146 Cheap Flights from Canada to Chicago Midway Airport in 2026

1 adult

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Find the cheapest flights from Canada to Chicago

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Canada to Chicago

Enter your travel dates to find the best prices.

6:45 a.m. - 10:05 a.m.

YUL

MDW

4h 20m

1 stop

11:00 a.m. - 6:15 p.m.

MDW

YUL

6h 15m

1 stop

C$ 254Porter Airlines

Wed, 1 Apr - Wed, 8 Apr

4:00 p.m. - 4:50 p.m.

YTZ

MDW

1h 50mdirect

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

MDW

YTZ

1h 40mdirect

C$ 262Porter Airlines

Fri, 29 May - Sun, 31 May

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

YTZ

MDW

1h 50mdirect

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

MDW

YTZ

1h 42mdirect

C$ 264Porter Airlines

Thu, 16 Apr - Wed, 22 Apr

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

YTZ

MDW

1h 50mdirect

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

MDW

YTZ

1h 42mdirect

C$ 270Air Transat

Thu, 19 Mar - Thu, 26 Mar

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

YTZ

MDW

1h 50mdirect

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

MDW

YTZ

1h 42mdirect

C$ 284Multiple Airlines

Wed, 11 Mar - Sat, 14 Mar

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

YTZ

MDW

1h 50mdirect

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

MDW

YTZ

1h 42mdirect

C$ 285Multiple Airlines

Thu, 19 Mar - Thu, 26 Mar

12:50 p.m. - 5:54 p.m.

YUL

MDW

6h 04m

1 stop

6:34 p.m. - 11:13 p.m.

MDW

YUL

3h 39m

1 stop

C$ 298Delta

Thu, 12 Mar - Mon, 16 Mar

6:10 a.m. - 8:54 a.m.

YYZ

MDW

3h 44m

1 stop

9:34 a.m. - 4:10 p.m.

MDW

YYZ

5h 36m

1 stop

C$ 320Delta

Thu, 26 Feb - Thu, 5 Mar

7:00 a.m. - 1:25 p.m.

YUL

MDW

7h 25m

1 stop

2:05 p.m. - 11:40 p.m.

MDW

YUL

8h 35m

1 stop

C$ 352WestJet

Wed, 11 Mar - Mon, 16 Mar

6:15 a.m. - 8:54 a.m.

YYZ

MDW

3h 39m

1 stop

1:29 p.m. - 7:09 p.m.

MDW

YYZ

4h 40m

1 stop

C$ 354WestJet

Wed, 4 Mar - Fri, 6 Mar

WestJet flights from Canada to Chicago Midway Airport

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

WestJet

11 Mar

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

7h 25m

1 stop

MDW1:25 p.m.Chicago Midway

16 Mar

MDW2:05 p.m.Chicago Midway

8h 35m

1 stop

YUL11:40 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 352

WestJet

4 Mar

YYZ6:15 a.m.Toronto Pearson Intl

3h 39m

1 stop

MDW8:54 a.m.Chicago Midway

6 Mar

MDW1:29 p.m.Chicago Midway

4h 40m

1 stop

YYZ7:09 p.m.Toronto Pearson Intl

C$ 354

WestJet

2 Apr

YYZ12:15 p.m.Toronto Pearson Intl

6h 39m

1 stop

MDW5:54 p.m.Chicago Midway

6 Apr

MDW6:34 p.m.Chicago Midway

3h 05m

1 stop

YYZ10:39 p.m.Toronto Pearson Intl

C$ 369

Porter Airlines flights from Canada to Chicago Midway Airport

Our best Porter Airlines deals on Canada to Chicago Midway Airport flight tickets

Porter Airlines

1 Apr

YUL6:45 a.m.Montreal Pierre Elliott Trudeau Intl

4h 20m

1 stop

MDW10:05 a.m.Chicago Midway

8 Apr

MDW11:00 a.m.Chicago Midway

6h 15m

1 stop

YUL6:15 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 254

Porter Airlines

16 Apr

YTZ9:15 a.m.Toronto Island

1h 50m

MDW10:05 a.m.Chicago Midway

22 Apr

MDW11:00 a.m.Chicago Midway

1h 42m

YTZ1:42 p.m.Toronto Island

C$ 264

Porter Airlines

19 Mar

YTZ2:30 p.m.Toronto Island

1h 50m

MDW3:20 p.m.Chicago Midway

26 Mar

MDW11:00 a.m.Chicago Midway

1h 42m

YTZ1:42 p.m.Toronto Island

C$ 265

momondo 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

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 1/4

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Wed 8/4

11:00 a.m.-6:15 p.m.

1 stop6h 15m

C$ 254

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 29/5

4:00 p.m.-4:50 p.m.

Nonstop1h 50m

Chicago Midway

Sun 31/5

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

Nonstop1h 40m

C$ 262

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 16/4

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

Nonstop1h 50m

Chicago Midway

Wed 22/4

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

Nonstop1h 42m

C$ 264

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/3

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

Nonstop1h 50m

Chicago Midway

Thu 26/3

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

Nonstop1h 42m

C$ 270

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 11/3

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

Nonstop1h 50m

Chicago Midway

Sat 14/3

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

Nonstop1h 42m

C$ 284

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/3

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

Nonstop1h 50m

Chicago Midway

Thu 26/3

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

Nonstop1h 42m

C$ 285

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 12/3

12:50 p.m.-5:54 p.m.

1 stop6h 04m

Chicago Midway

Mon 16/3

6:34 p.m.-11:13 p.m.

1 stop3h 39m

C$ 298

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 26/2

6:10 a.m.-8:54 a.m.

1 stop3h 44m

Chicago Midway

Thu 5/3

9:34 a.m.-4:10 p.m.

1 stop5h 36m

C$ 320

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 11/3

7:00 a.m.-1:25 p.m.

1 stop7h 25m

Chicago Midway

Mon 16/3

2:05 p.m.-11:40 p.m.

1 stop8h 35m

C$ 352

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 4/3

6:15 a.m.-8:54 a.m.

1 stop3h 39m

Chicago Midway

Fri 6/3

1:29 p.m.-7:09 p.m.

1 stop4h 40m

C$ 354

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 Canada to Chicago Midway Airport

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 Chicago Midway Airport?

In general, September is the cheapest month to fly from Canada to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 235. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Canada during the month January is also very affordable. Most momondo users find prices during this month for around C$ 262.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

The cheapest day to depart on your flight to Chicago Midway Airport is on a Monday when prices can be found for as low as C$ 267. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Canada because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 292.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is in the morning. Flights from Canada to Chicago Midway Airport during this time can be as low as C$ 279. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 662.

What is the cheapest Canada to Chicago Midway flight route?

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

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

There is only 1 cabin class available to choose from on Canada to Chicago Midway 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 Canada to Chicago Midway Airport flights?

You could potentially save up to 21% on your flight if you consider stops on a Canada to Chicago Midway Airport flight.

Cheap Canada to Chicago Midway Airport flight deals and tips

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

Best price found	C$ 205
Fastest flight time	1h 50m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from Canada in the past 72 hours is C$ 205. The best round-trip flight deal from Canada to Chicago Midway Airport found on momondo in the last 72 hours is C$ 262.

The fastest flight from Canada to Chicago Midway Airport takes 1h 50m

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

Search flight deals

When did momondo last update prices for flights from Canada to Chicago Midway Airport?
Prices for flights from Canada to Chicago Midway Airport are updated daily.
How many operators does momondo search for flights from Canada to Chicago Midway Airport?
As of February 2026, there is 1 operator available to choose from for flights from Canada to Chicago Midway Airport.
How old do you have to be to fly from Canada to Chicago Midway Airport?
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 Canada to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Canada to Chicago Midway Airport?
Based on momondo bookings for flights between Canada and Chicago Midway Airport, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 31.82% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 16.45%, Embraer 170 with 15.37%, and Embraer 175 with 10.37%.

Best airlines flying from Canada to Chicago Midway Airport

Compare and see reviews for airlines that fly from Canada to Chicago Midway Airport with momondo

Airline	Rating	Free Cancellation	Price
Porter Airlines	PriceFrom C$ 112	Free Cancellation	Rating 7.9 412 reviews		Search Porter Airlines flights

Munster

Hammond

Merrillville

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Canada.

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

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

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

Once you have performed a search for Canada to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Chicago from Canada. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago Midway Airport 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.

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Cheap flights from Canada to Chicago from C$ 146

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Canada to Chicago departing on 31/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names, great deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Canada to Chicago

Recent round-trip flight deals from Canada to Chicago

Recent one-way flight deals from Canada to Chicago

Recent last minute flight deals from Canada to Chicago

Recent direct flight deals from Canada to Chicago

WestJet flights from Canada to Chicago Midway Airport

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

Porter Airlines flights from Canada to Chicago Midway Airport

Our best Porter Airlines deals on Canada to Chicago Midway Airport flight tickets

momondo Fare Finder

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

See travel insights to Chicago from

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

What is the cheapest month to fly to Chicago Midway Airport?

What is the cheapest day to depart on your flight to Chicago Midway Airport?

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

What is the cheapest Canada to Chicago Midway flight route?

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

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

There is only 1 cabin class available to choose from on Canada to Chicago Midway 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 Canada to Chicago Midway Airport flights?

You could potentially save up to 21% on your flight if you consider stops on a Canada to Chicago Midway Airport flight.

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

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

How often are flights from Canada to Chicago delayed?

Historically, on average around 15% of flights between Canada and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 108 minutes.

What is the most punctual flight time for Canada to Chicago 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 day of the week experiences the fewest flight delays on this route?

Tuesday 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.

Which airline has the best punctuality record on Canada to Chicago 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 many flights depart from Canada to Chicago Midway Airport on average per day?

As of February 2026, there are 1 flights per day flying from Canada to Chicago Midway Airport. The most common time of day flights depart is 9:00a.m., with 100% of flights taking off at noon.

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

As of February 2026, 10 flights take off from Canada and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.

How long does it take to fly to Chicago Midway Airport?

Cheap Canada to Chicago Midway Airport flight deals and tips

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

Best price found

Fastest flight time

Direct flights

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

How many operators does momondo search for flights from Canada to Chicago Midway Airport?

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

What documentation or ID do you need to fly to Chicago Midway Airport?

What is the most popular plane model from Canada to Chicago Midway Airport?

Best airlines flying from Canada to Chicago Midway Airport

Compare and see reviews for airlines that fly from Canada to Chicago Midway Airport with momondo

Travelling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago Midway Airport 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 Chicago

Popular Cities in the United States

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