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

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

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

As of December 2025, there are 18 flights per week flying from Canada to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 22% of flights taking off on this day.

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

On average, it takes 1h 54m to fly from Canada to Chicago Midway Airport if you fly out of Toronto (the most popular airport in Canada) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago Midway Airport). If you’re flying out of Montreal and into Chicago O'Hare Intl Airport, then the flight time is around 2h 35m.

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

Wednesday is statistically the day of the week which experiences the fewest number of 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 day?

As of December 2025, 2 flights take off from Canada and land in Chicago Midway Airport each day. The most common flight departure time for this route is 9:00AM, with 55% of daily flights taking off at noon.

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

According to our data, Porter Airlines have had the least number of 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?

Air Transat, Porter Airlines, 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 14% 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 107 minutes.

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

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

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

As of December 2025, 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?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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.

$119 Cheap Flights from Canada to Chicago Midway Airport in 2025/26

1 adult

0 bags

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? 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 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.

9:15 am - 10:05 am

YTZ

MDW

1h 50mnonstop

11:00 am - 1:42 pm

MDW

YTZ

1h 42mnonstop

$174Porter Airlines

Thu, Jan 22 - Thu, Jan 29

9:15 am - 10:05 am

YTZ

MDW

1h 50mnonstop

11:00 am - 1:42 pm

MDW

YTZ

1h 42mnonstop

$178Porter Airlines

Thu, Jan 22 - Thu, Jan 29

9:15 am - 10:05 am

YTZ

MDW

1h 50mnonstop

11:05 am - 1:47 pm

MDW

YTZ

1h 42mnonstop

$179Porter Airlines

Thu, Jan 22 - Thu, Jan 29

9:15 am - 10:05 am

YTZ

MDW

1h 50mnonstop

11:00 am - 1:42 pm

MDW

YTZ

1h 42mnonstop

$180Porter Airlines

Fri, Feb 20 - Mon, Feb 23

9:15 am - 10:05 am

YTZ

MDW

1h 50mnonstop

11:00 am - 1:42 pm

MDW

YTZ

1h 42mnonstop

$187Porter Airlines

Thu, Jan 29 - Sun, Feb 1

10:05 am - 12:46 pm

YYZ

MDW

3h 41m1 stop

1:26 pm - 7:08 pm

MDW

YYZ

4h 42m1 stop

$212Delta

Thu, Feb 5 - Sun, Feb 8

6:15 am - 12:46 pm

YYZ

MDW

7h 31m1 stop

9:50 am - 3:59 pm

MDW

YYZ

5h 09m1 stop

$213Delta

Tue, Feb 17 - Wed, Feb 25

9:00 pm - 8:43 am

YWG

MDW

35h 43m2 stops

5:01 pm - 3:07 pm

MDW

YWG

22h 06m1 stop

$239Multiple Airlines

Thu, Jan 22 - Thu, Jan 29

8:55 am - 10:19 pm

YYC

MDW

12h 24m1 stop

1:20 pm - 7:09 pm

MDW

YYC

30h 49m1 stop

$249Multiple Airlines

Thu, Jan 15 - Wed, Jan 21

6:00 am - 8:52 am

YYZ

MDW

3h 52m1 stop

9:50 am - 3:59 pm

MDW

YYZ

5h 09m1 stop

$260WestJet

Tue, Jan 6 - Tue, Jan 13

Delta flights from Canada to Chicago Midway Airport

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

Delta

Feb 5

YYZ10:05 amToronto Pearson Intl

3h 41m

1 stop

MDW12:46 pmChicago Midway

Feb 8

MDW1:26 pmChicago Midway

4h 42m

1 stop

YYZ7:08 pmToronto Pearson Intl

$212

Find similar

Delta

Feb 17

YYZ6:15 amToronto Pearson Intl

7h 31m

1 stop

MDW12:46 pmChicago Midway

Feb 25

MDW9:50 amChicago Midway

5h 09m

1 stop

YYZ3:59 pmToronto Pearson Intl

$213

Find similar

Delta

Jan 29

YYZ7:45 amToronto Pearson Intl

6h 01m

1 stop

MDW12:46 pmChicago Midway

Feb 1

MDW1:26 pmChicago Midway

4h 42m

1 stop

YYZ7:08 pmToronto Pearson Intl

$216

Find similar

WestJet flights from Canada to Chicago Midway Airport

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

WestJet

Jan 6

YYZ6:00 amToronto Pearson Intl

3h 52m

1 stop

MDW8:52 amChicago Midway

Jan 13

MDW9:50 amChicago Midway

5h 09m

1 stop

YYZ3:59 pmToronto Pearson Intl

$260

Find similar

WestJet

Jan 17

YYZ6:00 amToronto Pearson Intl

3h 52m

1 stop

MDW8:52 amChicago Midway

Feb 20

MDW1:26 pmChicago Midway

4h 43m

1 stop

YYZ7:09 pmToronto Pearson Intl

$266

Find similar

WestJet

Feb 20

YYZ10:05 amToronto Pearson Intl

3h 41m

1 stop

MDW12:46 pmChicago Midway

Mar 24

MDW6:35 pmChicago Midway

3h 03m

1 stop

YYZ10:38 pmToronto Pearson Intl

$269

Find similar

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

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/22

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Thu 1/29

11:00 am-1:42 pm

Nonstop1h 42m

$174

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/22

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Thu 1/29

11:00 am-1:42 pm

Nonstop1h 42m

$178

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/22

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Thu 1/29

11:05 am-1:47 pm

Nonstop1h 42m

$179

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 2/20

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Mon 2/23

11:00 am-1:42 pm

Nonstop1h 42m

$180

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/29

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sun 2/1

11:00 am-1:42 pm

Nonstop1h 42m

$187

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/5

10:05 am-12:46 pm

1 stop3h 41m

Chicago Midway

Sun 2/8

1:26 pm-7:08 pm

1 stop4h 42m

$212

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 2/17

6:15 am-12:46 pm

1 stop7h 31m

Chicago Midway

Wed 2/25

9:50 am-3:59 pm

1 stop5h 09m

$213

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 1/22

9:00 pm-8:43 am

2 stops35h 43m

Chicago Midway

Thu 1/29

5:01 pm-3:07 pm

1 stop22h 06m

$239

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 1/15

8:55 am-10:19 pm

1 stop12h 24m

Chicago Midway

Wed 1/21

1:20 pm-7:09 pm

1 stop30h 49m

$249

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 1/6

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Tue 1/13

9:50 am-3:59 pm

1 stop5h 09m

$260

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?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Canada, with most prices found around $172. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Canada during the month October is also very affordable. Most momondo users find prices during this month for around $201.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Canada. The lowest ticket price found for a Wednesday departure recently was $208. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Thursday is the most expensive day to depart from Canada because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $289.

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

Flying to Chicago Midway Airport from Canada in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $236 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $267. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 are 4 cabin classes 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?

No. A direct flight is the cheapest option for a flight between Canada 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	$116
Fastest flight time	1h 49m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from Canada in the past 72 hours is $116. The best round-trip flight deal from Canada to Chicago Midway Airport found on momondo in the last 72 hours is $183.

The fastest flight from Canada to Chicago Midway Airport takes 1h 49m

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 were last updated today.
How many operators does momondo search for flights from Canada to Chicago Midway Airport?
As of December 2025, 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?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 this flight route, the most popular plane model on flight routes from Canada to Chicago Midway Airport is De Havilland (Bombardier) DHC-8-400 Dash 8Q (31.21% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (14.85%), Boeing 737-800 (12.80%), and Embraer 175 (11.71%).

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 $158	Free Cancellation	Rating 8.0 397 reviews		Search Porter Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

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?

Yes. momondo enables you to select and highlight flights to Chicago from Canada with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Canada.

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

Yes. momondo can track prices for Canada to Chicago 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 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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Fri 1/9

Fri 1/16

Email me momondo's favorite deals

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

Find better results for your trip to Chicago

Popular cities in the United States

Flights to Newark Airportfrom $41

Flights to New York John F Kennedy Intl Airportfrom $49

Flights to New York LaGuardia Airportfrom $24

Flights to Dallas/Fort Worth Airportfrom $53

Flights to Chicago O'Hare Intl Airportfrom $53

Flights to Washington, D.C. Dulles Intl Airportfrom $49

Flights to Orlando Airportfrom $41

Flights to Washington, D.C. Reagan-National Airportfrom $60

Flights to Dallas Love Field Airport

Cheap flights from Canada to Chicago from $119

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 1/20. 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 and deals

Big names and 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 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

Delta flights from Canada to Chicago Midway Airport

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

WestJet flights from Canada to Chicago Midway Airport

Our best WestJet 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 are 4 cabin classes 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?

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

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

Air Transat, Porter Airlines, 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 14% 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 107 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 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?

Wednesday is statistically the day of the week which experiences the fewest number of 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 have had the least number of 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 December 2025, 2 flights take off from Canada and land in Chicago Midway Airport each day. The most common flight departure time for this route is 9:00AM, with 55% of daily flights taking off at noon.

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

As of December 2025, there are 18 flights per week flying from Canada to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 22% of 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

Traveling 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