What is the cheapest airline that flies from Chicago Midway to Toronto Pearson Intl?

Delta and WestJet are the most popular carriers operating from Chicago Midway to Toronto Pearson Intl

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

Generally, flights departing at night tend to experience fewer delays. Flights in the evening 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 which experiences the fewest number of delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

How often are flights from Chicago to Toronto delayed?

Historically, on average around 25% of flights between Chicago and Toronto have experienced a delay on any given week. The average delay length over the past 12 months has been 105 minutes.

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

According to our data, Contour have had the least number of delays on this route over the last 12 months; with about 25% of their flights experiencing any sort of delay.

How old do you have to be to fly from Chicago Midway Airport to Toronto Pearson Intl Airport?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Toronto Pearson Intl Airport.

What documentation or ID do you need to fly to Toronto Pearson Intl Airport?

The travel and health documents you'll need for your trip to Toronto Pearson Intl 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 Toronto Pearson Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$94 Cheap Flights from Chicago Midway Airport to Toronto Pearson Intl 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 Chicago Midway Airport to Toronto

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:33 am - 4:12 pm

MDW

YYZ

5h 39m1 stop

7:45 am - 12:46 pm

YYZ

MDW

6h 01m1 stop

$234Delta

Thu, Feb 5 - Mon, Feb 9

9:53 am - 3:59 pm

MDW

YYZ

5h 06m1 stop

6:00 am - 8:52 am

YYZ

MDW

3h 52m1 stop

$245Delta

Thu, Feb 5 - Sun, Feb 8

1:26 pm - 7:08 pm

MDW

YYZ

4h 42m1 stop

12:12 pm - 5:55 pm

YYZ

MDW

6h 43m1 stop

$251Delta

Thu, Jan 29 - Tue, Feb 3

1:26 pm - 7:08 pm

MDW

YYZ

4h 42m1 stop

6:30 am - 11:05 am

YYZ

MDW

5h 35m1 stop

$262Delta

Sat, Jan 31 - Sat, Feb 7

1:28 pm - 10:41 pm

MDW

YYZ

8h 13m1 stop

6:00 am - 8:52 am

YYZ

MDW

3h 52m1 stop

$268Delta

Fri, Jan 16 - Sun, Jan 18

1:49 pm - 11:13 pm

MDW

YYZ

8h 24m1 stop

7:45 am - 12:46 pm

YYZ

MDW

6h 01m1 stop

$279Delta

Thu, Jan 15 - Fri, Jan 23

4:31 pm - 2:16 pm

MDW

YYZ

20h 45m1 stop

6:00 am - 8:52 am

YYZ

MDW

3h 52m1 stop

$292Multiple Airlines

Mon, Jan 12 - Fri, Jan 16

6:14 pm - 9:04 am

MDW

YYZ

13h 50m1 stop

10:05 am - 12:48 pm

YYZ

MDW

3h 43m1 stop

$302WestJet

Wed, Jan 7 - Fri, Jan 9

6:14 pm - 10:41 pm

MDW

YYZ

3h 27m1 stop

10:05 am - 12:48 pm

YYZ

MDW

3h 43m1 stop

$303WestJet

Thu, Jan 8 - Wed, Jan 14

6:14 pm - 10:41 pm

MDW

YYZ

3h 27m1 stop

10:05 am - 12:48 pm

YYZ

MDW

3h 43m1 stop

$304WestJet

Wed, Jan 7 - Wed, Jan 14

Delta flights from Chicago Midway Airport to Toronto Pearson Intl Airport

Our best Delta deals on Chicago Midway Airport to Toronto Pearson Intl Airport flight tickets

Delta

Feb 5

MDW9:53 amChicago Midway

5h 06m

1 stop

YYZ3:59 pmToronto Pearson Intl

Feb 8

YYZ6:00 amToronto Pearson Intl

3h 52m

1 stop

MDW8:52 amChicago Midway

$234

Find similar

Delta

Feb 5

MDW1:26 pmChicago Midway

8h 16m

1 stop

YYZ10:42 pmToronto Pearson Intl

Feb 8

YYZ6:30 amToronto Pearson Intl

5h 35m

1 stop

MDW11:05 amChicago Midway

$245

Find similar

Delta

Jan 29

MDW1:26 pmChicago Midway

4h 42m

1 stop

YYZ7:08 pmToronto Pearson Intl

Feb 3

YYZ12:12 pmToronto Pearson Intl

6h 43m

1 stop

MDW5:55 pmChicago Midway

$251

Find similar

WestJet flights from Chicago Midway Airport to Toronto Pearson Intl Airport

Our best WestJet deals on Chicago Midway Airport to Toronto Pearson Intl Airport flight tickets

WestJet

Jan 7

MDW6:14 pmChicago Midway

13h 50m

1 stop

YYZ9:04 amToronto Pearson Intl

Jan 9

YYZ10:05 amToronto Pearson Intl

3h 43m

1 stop

MDW12:48 pmChicago Midway

$302

Find similar

WestJet

Jan 8

MDW1:28 pmChicago Midway

4h 45m

1 stop

YYZ7:13 pmToronto Pearson Intl

Jan 11

YYZ6:00 amToronto Pearson Intl

3h 52m

1 stop

MDW8:52 amChicago Midway

$303

Find similar

WestJet

Jan 14

MDW6:14 pmChicago Midway

3h 27m

1 stop

YYZ10:41 pmToronto Pearson Intl

Jan 21

YYZ12:21 pmToronto Pearson Intl

6h 08m

1 stop

MDW5:29 pmChicago Midway

$304

Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 2/5

9:33 am-4:12 pm

1 stop5h 39m

Toronto Pearson Intl

Mon 2/9

7:45 am-12:46 pm

1 stop6h 01m

$234

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 2/5

9:53 am-3:59 pm

1 stop5h 06m

Toronto Pearson Intl

Sun 2/8

6:00 am-8:52 am

1 stop3h 52m

$245

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 1/29

1:26 pm-7:08 pm

1 stop4h 42m

Toronto Pearson Intl

Tue 2/3

12:12 pm-5:55 pm

1 stop6h 43m

$251

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 1/31

1:26 pm-7:08 pm

1 stop4h 42m

Toronto Pearson Intl

Sat 2/7

6:30 am-11:05 am

1 stop5h 35m

$262

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 1/16

1:28 pm-10:41 pm

1 stop8h 13m

Toronto Pearson Intl

Sun 1/18

6:00 am-8:52 am

1 stop3h 52m

$268

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 1/15

1:49 pm-11:13 pm

1 stop8h 24m

Toronto Pearson Intl

Fri 1/23

7:45 am-12:46 pm

1 stop6h 01m

$279

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Mon 1/12

4:31 pm-2:16 pm

1 stop20h 45m

Toronto Pearson Intl

Fri 1/16

6:00 am-8:52 am

1 stop3h 52m

$292

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 1/7

6:14 pm-9:04 am

1 stop13h 50m

Toronto Pearson Intl

Fri 1/9

10:05 am-12:48 pm

1 stop3h 43m

$302

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 1/8

6:14 pm-10:41 pm

1 stop3h 27m

Toronto Pearson Intl

Wed 1/14

10:05 am-12:48 pm

1 stop3h 43m

$303

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Wed 1/7

6:14 pm-10:41 pm

1 stop3h 27m

Toronto Pearson Intl

Wed 1/14

10:05 am-12:48 pm

1 stop3h 43m

$304

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 Toronto Pearson Intl 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

What is the cheapest day to depart on your flight to Toronto Pearson Intl Airport?

The cheapest day to depart from Chicago Midway Airport to Toronto Pearson Intl Airport is on a Thursday when prices can be found for as low as $568. The most expensive day to fly to Toronto Pearson Intl Airport is Sunday, with ticket prices averaging around $760.

What is the cheapest time of day to depart on your flight to Toronto Pearson Intl Airport?

Flying to Toronto Pearson Intl Airport from Chicago Midway Airport in the morning is the least expensive time of day to depart. momondo users have found prices as low as $565 when looking at flights departing in the morning. Flights in the afternoon are often more expensive with an average ticket price of $753.

When to book flights from Chicago Midway Airport to Toronto Pearson Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Toronto Pearson Intl Airport according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Toronto Pearson Intl Airport (MDW to YYZ) flight deals and tips

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

Fastest flight time	3h 06m
Direct flights	None

The fastest flight from Chicago Midway Airport to Toronto Pearson Intl Airport takes 3h 06m

There are no direct flights from Chicago Midway Airport to Toronto Pearson Intl Airport. There are no popular flight routes from Chicago Midway Airport to Toronto Pearson Intl Airport.

Search flight deals

How far is Chicago Midway to Toronto Pearson Intl by plane?
The distance between Chicago Midway and Toronto Pearson Intl is about 432.2 mi. A reasonable flight in good conditions will take 3h 06m.
When did momondo last update prices for flights from Chicago Midway Airport to Toronto Pearson Intl Airport?
Prices for flights from Chicago Midway Airport to Toronto Pearson Intl Airport are refreshed on a daily basis.
How old do you have to be to fly from Chicago Midway Airport to Toronto Pearson Intl Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Toronto Pearson Intl Airport.
What documentation or ID do you need to fly to Toronto Pearson Intl Airport?
The travel and health documents you'll need for your trip to Toronto Pearson Intl 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 Toronto Pearson Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Niagara Falls

Mississauga

Niagara-on-the-Lake

Brampton

Markham

Vaughan

Richmond Hill

Oakville

Kitchener

Barrie

Cambridge

Guelph

Burlington

Peterborough

Whitby

Collingwood

Milton

Orillia

Stratford

St. Catharines

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Toronto. momondo saves you time and could save you money on your trip.

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

Yes. All flights to Toronto from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once all potential Chicago to Toronto 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 Toronto right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Toronto from Chicago. 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 Toronto Pearson Intl 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

Sat 1/17

Sat 1/24

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 Toronto

Popular cities in Canada

Flights to Montreal Pierre Elliott Trudeau Intl Airportfrom $161

Flights to Toronto Island Airportfrom $138

Flights to Vancouver Intl Airport

Flights to Toronto Region of Waterloo Intl Airportfrom $214

Cheap flights from Chicago Midway Airport to Toronto from $94

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 Toronto departing on 2/21. 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 Chicago Midway Airport to Toronto

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Delta flights from Chicago Midway Airport to Toronto Pearson Intl Airport

Our best Delta deals on Chicago Midway Airport to Toronto Pearson Intl Airport flight tickets

WestJet flights from Chicago Midway Airport to Toronto Pearson Intl Airport

Our best WestJet deals on Chicago Midway Airport to Toronto Pearson Intl Airport flight tickets

momondo Fare Finder

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

See travel insights to Toronto from

How to get the cheapest flight ticket from Chicago Midway Airport to Toronto Pearson Intl Airport

What is the cheapest day to depart on your flight to Toronto Pearson Intl Airport?

The cheapest day to depart from Chicago Midway Airport to Toronto Pearson Intl Airport is on a Thursday when prices can be found for as low as $568. The most expensive day to fly to Toronto Pearson Intl Airport is Sunday, with ticket prices averaging around $760.

What is the cheapest time of day to depart on your flight to Toronto Pearson Intl Airport?

What is the cheapest airline that flies from Chicago Midway to Toronto Pearson Intl?

Delta and WestJet are the most popular carriers operating from Chicago Midway to Toronto Pearson Intl

How often are flights from Chicago to Toronto delayed?

Historically, on average around 25% of flights between Chicago and Toronto have experienced a delay on any given week. The average delay length over the past 12 months has been 105 minutes.

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

Generally, flights departing at night tend to experience fewer delays. Flights in the evening 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 which experiences the fewest number of delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

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

According to our data, Contour have had the least number of delays on this route over the last 12 months; with about 25% of their flights experiencing any sort of delay.

When to book flights from Chicago Midway Airport to Toronto Pearson Intl Airport

Cheap Chicago Midway Airport to Toronto Pearson Intl Airport (MDW to YYZ) flight deals and tips

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

Fastest flight time

Direct flights

How far is Chicago Midway to Toronto Pearson Intl by plane?

When did momondo last update prices for flights from Chicago Midway Airport to Toronto Pearson Intl Airport?

How old do you have to be to fly from Chicago Midway Airport to Toronto Pearson Intl Airport?

What documentation or ID do you need to fly to Toronto Pearson Intl Airport?

Traveling to a place near Toronto?

Why use momondo?

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

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

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

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

An easier way to manage your Toronto Pearson Intl 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 Toronto

Popular cities in Canada

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