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. 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 22% 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 91 minutes.

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

Delta is the most popular carrier operating from Chicago Midway to Toronto Pearson Intl

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

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

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 2026

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Find the cheapest flights from Chicago Midway Airport to Toronto

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

1:49 pm - 11:14 pm

MDW

YYZ

8h 25m

1 stop

12:09 pm - 6:25 pm

YYZ

MDW

7h 16m

1 stop

$243Delta

Thu, Jul 9 - Tue, Jul 14

9:27 am - 3:20 pm

MDW

YYZ

4h 53m

1 stop

2:15 pm - 5:58 pm

YYZ

MDW

4h 43m

1 stop

$247Delta

Fri, May 1 - Sun, May 3

9:20 am - 5:24 pm

MDW

YYZ

7h 04m

1 stop

12:09 pm - 6:02 pm

YYZ

MDW

6h 53m

1 stop

$250Delta

Sat, Jul 25 - Sat, Aug 1

6:38 pm - 10:56 pm

MDW

YYZ

3h 18m

1 stop

2:15 pm - 5:58 pm

YYZ

MDW

4h 43m

1 stop

$253Delta

Sat, Apr 25 - Sat, May 2

9:20 am - 5:24 pm

MDW

YYZ

7h 04m

1 stop

2:15 pm - 6:31 pm

YYZ

MDW

5h 16m

1 stop

$254Delta

Thu, Aug 6 - Tue, Aug 11

1:49 pm - 11:14 pm

MDW

YYZ

8h 25m

1 stop

6:10 am - 12:36 pm

YYZ

MDW

7h 26m

1 stop

$258Delta

Fri, Jun 26 - Mon, Jun 29

9:23 am - 6:31 pm

MDW

YYZ

8h 08m

1 stop

12:09 pm - 6:31 pm

YYZ

MDW

7h 22m

1 stop

$269Delta

Fri, Jun 5 - Wed, Jun 10

1:00 pm - 5:23 pm

MDW

YYZ

3h 23m

1 stop

6:00 am - 12:30 pm

YYZ

MDW

7h 30m

1 stop

$273Delta

Tue, Sep 15 - Thu, Sep 17

1:49 pm - 11:14 pm

MDW

YYZ

8h 25m

1 stop

12:09 pm - 6:25 pm

YYZ

MDW

7h 16m

1 stop

$281Delta

Fri, Jul 17 - Tue, Jul 21

9:20 am - 5:24 pm

MDW

YYZ

7h 04m

1 stop

6:10 am - 12:33 pm

YYZ

MDW

7h 23m

1 stop

$284Delta

Thu, Aug 6 - Sun, Aug 9

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

Jul 9

MDW1:49 pmChicago Midway

8h 25m

1 stop

YYZ11:14 pmToronto Pearson Intl

Jul 14

YYZ12:09 pmToronto Pearson Intl

7h 16m

1 stop

MDW6:25 pmChicago Midway

$243

Delta

May 1

MDW9:29 amChicago Midway

8h 02m

1 stop

YYZ6:31 pmToronto Pearson Intl

May 3

YYZ6:10 amToronto Pearson Intl

3h 37m

1 stop

MDW8:47 amChicago Midway

$247

Delta

Jul 25

MDW9:20 amChicago Midway

7h 04m

1 stop

YYZ5:24 pmToronto Pearson Intl

Aug 1

YYZ12:09 pmToronto Pearson Intl

6h 53m

1 stop

MDW6:02 pmChicago Midway

$250

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

May 1

MDW9:27 amChicago Midway

6h 54m

1 stop

YYZ5:21 pmToronto Pearson Intl

May 3

YYZ12:16 pmToronto Pearson Intl

6h 42m

1 stop

MDW5:58 pmChicago Midway

$406

WestJet

Apr 25

MDW6:38 pmChicago Midway

15h 40m

1 stop

YYZ11:18 amToronto Pearson Intl

Apr 27

YYZ2:15 pmToronto Pearson Intl

4h 43m

1 stop

MDW5:58 pmChicago Midway

$414

WestJet

Apr 11

MDW6:34 pmChicago Midway

3h 05m

1 stop

YYZ10:39 pmToronto Pearson Intl

Apr 15

YYZ2:15 pmToronto Pearson Intl

4h 43m

1 stop

MDW5:58 pmChicago Midway

$479

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

Cheapest round-trip

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 7/9

1:49 pm-11:14 pm

1 stop8h 25m

Toronto Pearson Intl

Tue 7/14

12:09 pm-6:25 pm

1 stop7h 16m

$243

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 5/1

9:27 am-3:20 pm

1 stop4h 53m

Toronto Pearson Intl

Sun 5/3

2:15 pm-5:58 pm

1 stop4h 43m

$247

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 7/25

9:20 am-5:24 pm

1 stop7h 04m

Toronto Pearson Intl

Sat 8/1

12:09 pm-6:02 pm

1 stop6h 53m

$250

Quickest round-trip

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 4/25

6:38 pm-10:56 pm

1 stop3h 18m

Toronto Pearson Intl

Sat 5/2

2:15 pm-5:58 pm

1 stop4h 43m

$253

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 8/6

9:20 am-5:24 pm

1 stop7h 04m

Toronto Pearson Intl

Tue 8/11

2:15 pm-6:31 pm

1 stop5h 16m

$254

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 6/26

1:49 pm-11:14 pm

1 stop8h 25m

Toronto Pearson Intl

Mon 6/29

6:10 am-12:36 pm

1 stop7h 26m

$258

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 6/5

9:23 am-6:31 pm

1 stop8h 08m

Toronto Pearson Intl

Wed 6/10

12:09 pm-6:31 pm

1 stop7h 22m

$269

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 9/15

1:00 pm-5:23 pm

1 stop3h 23m

Toronto Pearson Intl

Thu 9/17

6:00 am-12:30 pm

1 stop7h 30m

$273

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Fri 7/17

1:49 pm-11:14 pm

1 stop8h 25m

Toronto Pearson Intl

Tue 7/21

12:09 pm-6:25 pm

1 stop7h 16m

$281

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 8/6

9:20 am-5:24 pm

1 stop7h 04m

Toronto Pearson Intl

Sun 8/9

6:10 am-12:33 pm

1 stop7h 23m

$284

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

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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 $443. The most expensive day to fly to Toronto Pearson Intl Airport is Sunday, with ticket prices averaging around $730.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $413 when looking at flights departing in the evening. Flights in the afternoon are often more expensive with an average ticket price of $737.

Can stopping save me money on Chicago Midway Airport to Toronto Pearson Intl Airport flights?

You could potentially save up to 20% on your flight if you consider stops on a Chicago Midway Airport to Toronto Pearson Intl Airport flight.

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 17m
Direct flights	None

The fastest flight from Chicago Midway Airport to Toronto Pearson Intl Airport takes 3h 17m

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.

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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 17m.
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 many operators does momondo search for flights from Chicago Midway Airport to Toronto Pearson Intl Airport?
There is 1 operator available for flights from Chicago Midway Airport to Toronto Pearson Intl Airport as of March 2026.
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.
What is the most popular airline from Chicago Midway Airport to Toronto Pearson Intl Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago Midway Airport to Toronto Pearson Intl Airport is Delta (100% of total bookings).

Best airlines flying from Chicago Midway Airport to Toronto Pearson Intl Airport

Compare and see reviews for airlines that fly from Chicago Midway Airport to Toronto Pearson Intl Airport with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $88	Free Cancellation	Rating 7.9 8,356 reviews		Search Delta flights

Niagara Falls

Mississauga

Niagara-on-the-Lake

Brampton

Markham

Vaughan

Richmond Hill

Oakville

Barrie

Kitchener

St. Catharines

Collingwood

Cambridge

Burlington

Guelph

Peterborough

Whitby

Orillia

Oshawa

Stratford

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

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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 5/1. 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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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?

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

Can stopping save me money on Chicago Midway Airport to Toronto Pearson Intl Airport flights?

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

How often are flights from Chicago to Toronto delayed?

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

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

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

Best airlines flying from Chicago Midway Airport to Toronto Pearson Intl Airport

Compare and see reviews for airlines that fly from Chicago Midway Airport to Toronto Pearson Intl Airport with momondo

Traveling to a place near Toronto?

Why use momondo?

An easier way to manage your Toronto Pearson Intl Airport trip

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