How often are flights from Chicago to Canada delayed?

Historically, on average around 18% 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 111 minutes.

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

Saturday 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.

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

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

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

Delta is the most popular carrier operating from Chicago Midway to Canada

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

According to our data, Porter Airlines have had the least number of delays on this route over the last 12 months; with about 17% of their flights experiencing any sort of delay.

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

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

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

The number of operators available for flights from Chicago Midway Airport to Canada is 2 as of November 2026.

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

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 Chicago Midway Airport to Canada.

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

The required travel and health documents for your Canada trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Canada. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$135 Cheap Flights from Chicago Midway Airport to Canada in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago Midway Airport to Canada

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:29 am - 3:14 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

4h 45m1 stop Detroit Metropolitan Wayne County

6:10 am - 8:49 amYYZ Toronto Pearson Intl-MDW Chicago Midway

3h 39m1 stop Detroit Metropolitan Wayne County

$400Delta

Tue, Dec 22 - Tue, Dec 29

9:37 am - 5:20 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

6h 43m1 stop Detroit Metropolitan Wayne County

2:25 pm - 6:01 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 36m1 stop Detroit Metropolitan Wayne County

$402Delta

Thu, Dec 3 - Sun, Dec 6

6:41 pm - 11:07 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

3h 26m1 stop Detroit Metropolitan Wayne County

2:25 pm - 6:01 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 36m1 stop Detroit Metropolitan Wayne County

$402Air France

Thu, Dec 3 - Sun, Dec 6

9:37 am - 5:20 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

6h 43m1 stop Detroit Metropolitan Wayne County

2:25 pm - 6:01 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 36m1 stop Detroit Metropolitan Wayne County

$407Delta

Thu, Dec 3 - Sun, Dec 6

1:59 pm - 7:14 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

4h 15m1 stop Detroit Metropolitan Wayne County

9:45 am - 1:01 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 16m1 stop Detroit Metropolitan Wayne County

$408Delta

Wed, Jan 13 - Tue, Jan 19

1:41 pm - 11:07 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

8h 26m1 stop Detroit Metropolitan Wayne County

2:25 pm - 6:01 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 36m1 stop Detroit Metropolitan Wayne County

$408Delta

Fri, Dec 11 - Tue, Dec 15

6:41 pm - 11:07 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

3h 26m1 stop Detroit Metropolitan Wayne County

6:00 am - 9:37 amYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 37m1 stop Detroit Metropolitan Wayne County

$408Delta

Sat, Dec 12 - Mon, Dec 14

1:00 pm - 5:22 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

3h 22m1 stop Detroit Metropolitan Wayne County

12:15 pm - 6:37 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

7h 22m1 stop Detroit Metropolitan Wayne County

$408Delta

Thu, Apr 8 - Tue, Apr 13

6:41 pm - 11:07 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

3h 26m1 stop Detroit Metropolitan Wayne County

6:00 am - 9:37 amYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 37m1 stop Detroit Metropolitan Wayne County

$408Delta

Mon, Dec 7 - Mon, Dec 14

5:34 pm - 2:40 pmMDW Chicago Midway-YWG Winnipeg

20h 06m1 stop Atlanta Hartsfield-Jackson

7:00 am - 11:46 pmYWG Winnipeg-MDW Chicago Midway

17h 46m1 stop Atlanta Hartsfield-Jackson

$410Multiple Airlines

Tue, Jan 19 - Wed, Feb 3

Cheap last minute flights

Enter your travel dates to find the best prices.

10:34 am - 12:17 amMDW Chicago Midway-YYC Calgary

13h 43m2 stops Minneapolis St Paul Salt Lake City

7:25 am - 4:50 pmYYC Calgary-MDW Chicago Midway

9h 25m2 stops Salt Lake City Minneapolis St Paul

$443Delta

Fri, Nov 13 - Tue, Dec 8

10:34 am - 12:17 amMDW Chicago Midway-YYC Calgary

13h 43m2 stops Minneapolis St Paul Salt Lake City

7:25 am - 6:04 pmYYC Calgary-MDW Chicago Midway

10h 39m2 stops Salt Lake City Detroit Metropolitan Wayne County

$443Delta

Fri, Nov 13 - Wed, Nov 18

12:30 pm - 12:17 amMDW Chicago Midway-YYC Calgary

11h 47m2 stops Minneapolis St Paul Salt Lake City

8:45 am - 4:39 pmYYC Calgary-MDW Chicago Midway

7h 54m1 stop Minneapolis St Paul

$475Delta

Fri, Nov 13 - Wed, Nov 18

12:30 pm - 9:58 pmMDW Chicago Midway-YYC Calgary

9h 28m1 stop Minneapolis St Paul

7:25 am - 6:01 pmYYC Calgary-MDW Chicago Midway

10h 36m2 stops Salt Lake City Detroit Metropolitan Wayne County

$518Delta

Fri, Nov 13 - Tue, Dec 8

12:30 pm - 9:58 pmMDW Chicago Midway-YYC Calgary

9h 28m1 stop Minneapolis St Paul

8:45 am - 4:39 pmYYC Calgary-MDW Chicago Midway

7h 54m1 stop Minneapolis St Paul

$546Delta

Fri, Nov 13 - Wed, Nov 18

6:42 pm - 1:40 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

17h 58m2 stops Atlanta Hartsfield-Jackson Orlando

9:35 am - 7:47 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

11h 12m1 stop Orlando

$552Multiple Airlines

Wed, Nov 11 - Wed, Nov 25

6:00 am - 4:15 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

9h 15m1 stop Atlanta Hartsfield-Jackson

12:15 pm - 6:04 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

6h 49m1 stop Detroit Metropolitan Wayne County

$572Delta

Wed, Nov 11 - Wed, Nov 25

9:30 am - 1:30 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

3h 00m1 stop Detroit Metropolitan Wayne County

9:45 am - 12:51 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 06m1 stop Detroit Metropolitan Wayne County

$572Delta

Tue, Nov 10 - Tue, Nov 24

9:30 am - 5:20 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

6h 50m1 stop Detroit Metropolitan Wayne County

6:00 am - 11:25 amYYZ Toronto Pearson Intl-MDW Chicago Midway

6h 25m1 stop Detroit Metropolitan Wayne County

$572Delta

Wed, Nov 11 - Thu, Nov 26

6:42 pm - 3:20 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

19h 38m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale

7:35 am - 11:47 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

17h 12m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson

$587Multiple Airlines

Thu, Nov 12 - Mon, Nov 16

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Delta flights from Chicago Midway Airport to Canada

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

Delta

Dec 22

MDW9:29 amChicago Midway

4h 45m

1 stop

YYZ3:14 pmToronto Pearson Intl

Dec 29

YYZ6:10 amToronto Pearson Intl

3h 39m

1 stop

MDW8:49 amChicago Midway

$400

Delta

Dec 3

MDW9:37 amChicago Midway

6h 43m

1 stop

YYZ5:20 pmToronto Pearson Intl

Dec 6

YYZ2:25 pmToronto Pearson Intl

4h 36m

1 stop

MDW6:01 pmChicago Midway

$402

Delta

Dec 3

MDW9:37 amChicago Midway

6h 43m

1 stop

YYZ5:20 pmToronto Pearson Intl

Dec 6

YYZ2:25 pmToronto Pearson Intl

4h 36m

1 stop

MDW6:01 pmChicago Midway

$407

Air France flights from Chicago Midway Airport to Canada

Our best Air France deals on Chicago Midway Airport to Canada flight tickets

Air France

Dec 3

MDW9:37 amChicago Midway

6h 43m

1 stop

YYZ5:20 pmToronto Pearson Intl

Dec 6

YYZ2:25 pmToronto Pearson Intl

4h 36m

1 stop

MDW6:01 pmChicago Midway

$419

Air France

Dec 10

MDW12:39 pmChicago Midway

9h 28m

1 stop

YYC10:07 pmCalgary

Dec 17

YYC8:45 amCalgary

8h 05m

1 stop

MDW4:50 pmChicago Midway

$533

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

Cheapest round-trip

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Tue 12/22

9:29 am-3:14 pm

1 stop4h 45m

Toronto Pearson Intl

Tue 12/29

6:10 am-8:49 am

1 stop3h 39m

$400

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Thu 12/3

9:37 am-5:20 pm

1 stop6h 43m

Toronto Pearson Intl

Sun 12/6

2:25 pm-6:01 pm

1 stop4h 36m

$402

Quickest round-trip

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Thu 12/3

6:41 pm-11:07 pm

1 stop3h 26m

Toronto Pearson Intl

Sun 12/6

2:25 pm-6:01 pm

1 stop4h 36m

$402

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Thu 12/3

9:37 am-5:20 pm

1 stop6h 43m

Toronto Pearson Intl

Sun 12/6

2:25 pm-6:01 pm

1 stop4h 36m

$407

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Wed 1/13

1:59 pm-7:14 pm

1 stop4h 15m

Toronto Pearson Intl

Tue 1/19

9:45 am-1:01 pm

1 stop4h 16m

$408

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Fri 12/11

1:41 pm-11:07 pm

1 stop8h 26m

Toronto Pearson Intl

Tue 12/15

2:25 pm-6:01 pm

1 stop4h 36m

$408

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Sat 12/12

6:41 pm-11:07 pm

1 stop3h 26m

Toronto Pearson Intl

Mon 12/14

6:00 am-9:37 am

1 stop4h 37m

$408

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Thu 4/8

1:00 pm-5:22 pm

1 stop3h 22m

Toronto Pearson Intl

Tue 4/13

12:15 pm-6:37 pm

1 stop7h 22m

$408

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Mon 12/7

6:41 pm-11:07 pm

1 stop3h 26m

Toronto Pearson Intl

Mon 12/14

6:00 am-9:37 am

1 stop4h 37m

$408

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Tue 1/19

5:34 pm-2:40 pm

1 stop20h 06m

Winnipeg

Wed 2/3

7:00 am-11:46 pm

1 stop17h 46m

$410

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

What is the cheapest month to fly to Canada?

If you aren’t able to travel during the month of January, then book flights to Canada from Chicago Midway Airport during April instead. Flights to Canada in April, while not as cheap as those in January, still average around $228.

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

Our data shows that Saturday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as $249. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Canada for around $345.

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

In the morning is the cheapest time of day to fly from Chicago Midway Airport to Canada when you can find flight prices for as low as $290. Flying to Canada in the morning is an ideal time because this is during off-peak travel hours. In contrast, the most expensive time of day to depart to Canada is in the afternoon when prices are around $300.

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 Airport to Canada flights?

There are 2 cabin classes available to choose from on Chicago Midway Airport 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?

You could potentially save up to 10% on your flight if you consider stops on a Chicago Midway Airport to Canada flight.

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	$135
Fastest flight time	3h 13m
Direct flights	None

The best one-way flight to Canada from Chicago Midway Airport in the past 72 hours is $135. The best round-trip flight deal from Chicago Midway Airport to Canada found on momondo in the last 72 hours is $400.

The fastest flight from Chicago Midway Airport to Canada takes 3h 13m

There are no direct flights from Chicago Midway Airport to Canada. There are no popular flight routes from Chicago Midway Airport to Canada.

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Canada

When did momondo last update prices for flights from Chicago Midway Airport to Canada?
Prices for flights from Chicago Midway Airport to Canada are updated daily.
How many operators does momondo search for flights from Chicago Midway Airport to Canada?
The number of operators available for flights from Chicago Midway Airport to Canada is 2 as of November 2026.
How old do you have to be to fly from Chicago Midway Airport to Canada?
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 Chicago Midway Airport to Canada.
What documentation or ID do you need to fly to Canada?
The required travel and health documents for your Canada trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Canada. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago Midway Airport to Canada?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Canada is De Havilland (Bombardier) DHC-8-400 Dash 8Q (40.35% of total bookings). The next most popular plane models are Embraer 175 (11.29%), Embraer 175 (Enhanced Winglets) (9.65%), and Embraer 170 (7.02%).

Best airlines flying from Chicago Midway Airport to Canada

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $106	Free Cancellation	Rating 7.8 8,702 reviews		Search Delta flights
Porter Airlines	PriceFrom $193	Free Cancellation	Rating 8.0 468 reviews		Search Porter Airlines flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Canada for you.

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

momondo does allow users to show only those flights to Canada from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search for Chicago to Canada 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 Chicago to Canada right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Canada, momondo offers a useful price alert feature which will track prices for flights to Canada from Chicago and alert you when they change.

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.

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Tue 12/8

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Find better results for your trip to Canada

Popular cities

Other flights from Chicago Midway Airport

Other flights to Canada

Airlines

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Complete your trip

Feeling lucky

Popular cities in Canada

Flights to Torontofrom $135

Flights to Vancouverfrom $124

Flights to Montrealfrom $225

Flights to Calgaryfrom $117

Flights to Ottawafrom $228

Flights to Halifaxfrom $348

Flights to Winnipegfrom $296

Flights to Québec Cityfrom $438

Flights to Kelownafrom $253

Flights to St. John'sfrom $442

Flights to Saskatoonfrom $296

Flights to Reginafrom $342

Cheap flights from Chicago Midway Airport to Canada from $135

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 12/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Chicago Midway Airport to Canada

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

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Price Alerts

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Delta flights from Chicago Midway Airport to Canada

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

Air France flights from Chicago Midway Airport to Canada

Our best Air France 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 Airport 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?

Cheap Chicago Midway Airport to Canada flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Chicago Midway Airport to Canada

Best airlines flying from Chicago Midway Airport to Canada

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

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 favorite 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