MDW - YYZ

$101 Find Cheap Flights from Chicago Midway Airport to Toronto Pearson Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Pearson Intl departing on 6/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Toronto Pearson Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Toronto, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Toronto, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$260
Typical prices: $404-$356
Delta
Fri 5/29Mon 6/1
MDW - YYZ • 1 stop
Cheapest one-way
$101
Delta
Fri 6/5
MDW - YYZ • 1 stop
Top airlines
Delta
Cheapest • from $260 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Midway and Pearson Intl. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
When to travel
July
Cheapest • 44% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Pearson Intl!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Pearson Intl (MDW-YYZ)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Pearson Intl that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Pearson Intl

Fri, May 29 - Mon, Jun 1
Delta Logo
1:59 pm - 11:14 pm
MDW
-
YYZ
8h 15m
1 stop
Delta Logo
12:09 pm - 6:33 pm
YYZ
-
MDW
7h 24m
1 stop
$260Delta
Tue, May 26 - Wed, Jun 3
Delta Logo
9:22 am - 5:21 pm
MDW
-
YYZ
6h 59m
1 stop
Delta Logo
6:30 am - 1:19 pm
YYZ
-
MDW
7h 49m
1 stop
$261Delta
Fri, May 29 - Tue, Jun 2
Delta Logo
1:59 pm - 11:14 pm
MDW
-
YYZ
8h 15m
1 stop
Delta Logo
2:20 pm - 6:33 pm
YYZ
-
MDW
5h 13m
1 stop
$269Delta
Fri, Jun 12 - Fri, Jun 19
Delta Logo
1:21 pm - 11:02 pm
MDW
-
YYZ
8h 41m
1 stop
Delta Logo
2:29 pm - 6:31 pm
YYZ
-
MDW
5h 02m
1 stop
$271Delta
Tue, Jun 23 - Wed, Jul 8
Delta Logo
9:17 am - 1:34 pm
MDW
-
YYZ
3h 17m
1 stop
Delta Logo
6:10 am - 9:08 am
YYZ
-
MDW
3h 58m
1 stop
$281Delta
Wed, Jun 3 - Sun, Jun 7
Delta Logo
6:36 pm - 10:59 pm
MDW
-
YYZ
3h 23m
1 stop
Delta Logo
6:05 am - 9:14 am
YYZ
-
MDW
4h 09m
1 stop
$286Delta
Thu, Jun 11 - Sun, Jun 14
Delta Logo
1:21 pm - 11:02 pm
MDW
-
YYZ
8h 41m
1 stop
Delta Logo
6:05 am - 9:14 am
YYZ
-
MDW
4h 09m
1 stop
$297Delta
Mon, Jul 13 - Wed, Jul 15
Delta Logo
9:19 am - 3:20 pm
MDW
-
YYZ
5h 01m
1 stop
Delta Logo
4:10 pm - 6:25 pm
YYZ
-
MDW
3h 15m
1 stop
$301Delta
Thu, Jun 25 - Sun, Jun 28
Delta Logo
9:17 am - 5:24 pm
MDW
-
YYZ
7h 07m
1 stop
Delta Logo
6:05 am - 12:41 pm
YYZ
-
MDW
7h 36m
1 stop
$307Delta
Sat, Jun 13 - Sat, Jun 27
Delta Logo
6:35 pm - 11:02 pm
MDW
-
YYZ
3h 27m
1 stop
Delta Logo
6:05 am - 12:41 pm
YYZ
-
MDW
7h 36m
1 stop
$309Delta
Booking Insights

KAYAK's insights & trends for Midway to Pearson Intl flights

Get data-powered insights and trends into flights from Midway to Pearson Intl to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago Midway Airport to Toronto Pearson Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Toronto Pearson Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Toronto Pearson Intl Airport is July, where tickets cost $211 (return) on average. On the other hand, the most expensive months are September and February, where the average cost of round-trip tickets is $824 and $673 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$101
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 19% lower on average.
Flight from Chicago Midway Airport to Toronto Pearson Airport

When to book flights from Midway to Pearson Intl

Are your dates flexible? Find out the best times to travel from Midway to Pearson Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Toronto Pearson Airport flights

  • What is the cheapest flight from Chicago Midway Airport to Toronto Pearson Intl Airport?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Toronto Pearson Intl Airport was $101 for a one-way ticket and $260 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Toronto Pearson Airport?

    Yes, you’ll need a passport to travel to Toronto Pearson Airport from Chicago Midway Airport.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Toronto Pearson Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Toronto Pearson Airport?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Toronto Pearson Airport.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Toronto Pearson Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Toronto Pearson Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Toronto Pearson Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Toronto Pearson Airport from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Toronto Pearson Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Toronto Pearson Airport with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and YYZ can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Toronto Pearson Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Toronto Pearson Airport from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Pearson Intl

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Toronto. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Pearson Intl? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8466 reviews
7.8Entertainment
7.2Food
8.5Crew
8.1Boarding
7.9Comfort
Airline reviews

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

6.0 GoodSilvestre, Apr 2026
MCO - GRU
Read more Delta reviews

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

Everything you need to know for your flight from Midway to Pearson Intl

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Pearson Intl (YYZ)