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$105 Find cheap flights from Chicago Midway Airport to Toronto

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 Toronto departing on 6/21. 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
0 bags
Fri 6/21
Fri 6/28

Search hundreds of travel sites at once for deals on flights to Toronto

 
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
In the last 7 days travelers have searched 43,423,329 times on KAYAK, and here is why:

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Cheap flight deals from Midway to Toronto (MDW-YTO)

 
These are the cheapest deals for flights from Midway to Toronto currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to Toronto

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Toronto.

Recent one-way flight deals from Midway to Toronto

Only flying one-way? Below are some of the best one-way flight deals from Midway to Toronto found on KAYAK recently.

Recent last minute flight deals from Midway to Toronto

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Midway to Toronto.

Recent direct flight deals from Midway to Toronto

The latest deals for direct flights from Midway to Toronto so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Midway to Toronto

Find recent round-trip train or bus tickets from Midway to Toronto.

All round-trip flight deals to Toronto

The cheapest plane tickets to Toronto found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:05 am - 1:47 pmMDW-YTZ
1h 42mnonstop
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
$245Porter Airlines
Find Deal
Tue, Jun 11 - Mon, Jun 17
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
$246Porter Airlines
Find Deal
Sat, Jun 8 - Wed, Jun 12
12:30 pm - 3:12 pmMDW-YTZ
1h 42mnonstop
6:15 pm - 7:02 pmYTZ-MDW
1h 47mnonstop
$248Porter Airlines
Find Deal
Sat, Jun 29 - Sat, Jul 6
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
$249Porter Airlines
Find Deal
Fri, Jul 26 - Fri, Jul 26
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
2:25 pm - 8:07 pmYTZ-MDW
6h 42m1 stop
$306
Find Deal
Sat, Jun 8 - Wed, Jun 12
5:15 pm - 7:57 pmMDW-YTZ
1h 42mnonstop
11:55 am - 8:08 pmYTZ-MDW
9h 13m1 stop
$311
Find Deal
Tue, Oct 1 - Sat, Oct 5
9:46 am - 6:20 pmMDW-YYZ
7h 34m1 stop
6:04 am - 8:48 amYYZ-MDW
3h 44m1 stop
$317Delta
Find Deal
Wed, Jun 5 - Tue, Jun 11
5:59 pm - 10:50 pmMDW-YYZ
3h 51m1 stop
12:30 pm - 6:05 pmYYZ-MDW
6h 35m1 stop
$319Delta
Find Deal
Sat, Sep 7 - Sat, Sep 14
9:46 am - 6:20 pmMDW-YYZ
7h 34m1 stop
7:23 pm - 6:36 pmYYZ-MDW
24h 13m1 stop
$350WestJet
Find Deal
Tue, Jun 4 - Mon, Jun 17
6:00 am - 12:10 pmMDW-YYZ
5h 10m1 stop
7:45 am - 6:05 pmYYZ-MDW
11h 20m1 stop
$355WestJet
Find Deal
Wed, Jul 3 - Tue, Jul 9
11:25 am - 2:07 pmMDW-YTZ
1h 42mnonstop
$105Porter Airlines
Find Deal
Fri, Jun 21
11:25 am - 2:07 pmMDW-YTZ
1h 42mnonstop
$107Porter Airlines
Find Deal
Thu, Jun 6
11:25 am - 2:07 pmMDW-YTZ
1h 42mnonstop
$111Porter Airlines
Find Deal
Thu, Jun 6
9:34 am - 5:08 pmMDW-YYZ
6h 34m1 stop
$132Delta
Find Deal
Wed, Jun 19
1:24 pm - 10:53 pmMDW-YYZ
8h 29m1 stop
$137Delta
Find Deal
Thu, Jul 18
9:29 am - 6:33 pmMDW-YYZ
8h 04m1 stop
$138KLM
Find Deal
Tue, Jun 11
10:08 am - 12:02 amMDW-YYZ
12h 54m1 stop
$147
Find Deal
Sat, Jun 1
3:45 pm - 9:58 pmMDW-YYZ
5h 13m1 stop
$154WestJet
Find Deal
Tue, Aug 6
2:00 pm - 6:10 amMDW-YYZ
15h 10m2 stops
$156WestJet
Find Deal
Fri, Sep 20
8:56 pm - 11:26 pmMDW-YYZ
25h 30m1 stop
$178
Find Deal
Mon, Jun 3
5:15 pm - 7:57 pmMDW-YTZ
1h 42mnonstop
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
$459Porter Airlines
Find Deal
Mon, May 27 - Wed, May 29
5:15 pm - 7:57 pmMDW-YTZ
1h 42mnonstop
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
$463Porter Airlines
Find Deal
Mon, May 27 - Wed, May 29
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
$502Porter Airlines
Find Deal
Thu, May 23 - Thu, May 30
5:15 pm - 7:57 pmMDW-YTZ
1h 42mnonstop
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
$504Porter Airlines
Find Deal
Fri, May 24 - Tue, May 28
6:00 am - 12:10 pmMDW-YYZ
5h 10m1 stop
12:30 pm - 6:07 pmYYZ-MDW
6h 37m1 stop
$538WestJet
Find Deal
Mon, May 27 - Wed, May 29
3:45 pm - 11:57 pmMDW-YYZ
7h 12m1 stop
6:17 am - 2:55 pmYYZ-MDW
9h 38m1 stop
$589WestJet
Find Deal
Sat, May 25 - Mon, May 27
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
9:35 pm - 7:43 pmYTZ-MDW
23h 08m3 stops
$648
Find Deal
Sat, May 25 - Thu, May 30
9:32 am - 5:09 pmMDW-YYZ
6h 37m1 stop
9:45 am - 12:40 pmYYZ-MDW
3h 55m1 stop
$662Delta
Find Deal
Sat, May 25 - Thu, May 30
2:15 pm - 11:14 pmMDW-YYZ
7h 59m1 stop
6:34 am - 11:02 amYYZ-MDW
5h 28m1 stop
$696Delta
Find Deal
Fri, May 24 - Sun, May 26
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
2:30 pm - 6:07 pmYTZ-MDW
28h 37m3 stops
$950
Find Deal
Sat, May 25 - Tue, May 28
11:05 am - 1:47 pmMDW-YTZ
1h 42mnonstop
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
$245Porter Airlines
Find Deal
Tue, Jun 11 - Mon, Jun 17
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
$246Porter Airlines
Find Deal
Sat, Jun 8 - Wed, Jun 12
12:30 pm - 3:12 pmMDW-YTZ
1h 42mnonstop
6:15 pm - 7:02 pmYTZ-MDW
1h 47mnonstop
$248Porter Airlines
Find Deal
Sat, Jun 29 - Sat, Jul 6
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
$249Porter Airlines
Find Deal
Fri, Jul 26 - Fri, Jul 26
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
$252Porter Airlines
Find Deal
Sat, Jun 8 - Tue, Jun 11
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
$253Porter Airlines
Find Deal
Thu, Jun 6 - Fri, Jun 7
5:15 pm - 7:57 pmMDW-YTZ
1h 42mnonstop
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
$257Porter Airlines
Find Deal
Fri, Jun 14 - Tue, Jun 25
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
$258Porter Airlines
Find Deal
Thu, Jun 13 - Wed, Jun 19
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
10:45 am - 11:32 amYTZ-MDW
1h 47mnonstop
$259Porter Airlines
Find Deal
Tue, Oct 1 - Sat, Oct 5
11:25 am - 2:07 pmMDW-YTZ
1h 42mnonstop
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
$261Porter Airlines
Find Deal
Fri, Jun 14 - Mon, Jun 24

Flights from Midway to Toronto - Travel Insights & Trends

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

What is the cheapest Chicago Midway Airport to Toronto flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago Midway Airport to Toronto.
Our data shows that the cheapest route for a one-way flight from Chicago Midway Airport to Toronto cost $105 and was between Chicago Midway Airport and Toronto Island Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $159.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Toronto?

The average price of all flights from Chicago Midway Airport to Toronto clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Toronto on a Tuesday and more expensive on a Friday. On your return trip to Chicago Midway Airport, you should consider flying back on a Monday, and avoid Fridays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Toronto, 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 is January, where tickets cost $270 on average. On the other hand, the most expensive months are September and November, where the average cost of tickets is $386 and $384 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Toronto?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Toronto, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Toronto, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 69 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Toronto?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago Midway Airport to Toronto found by KAYAK users in the last 72 hours was for $245 on Porter Airlines, followed by Delta ($317). One-way flight deals have also been found from as low as $105 on Porter Airlines and from $132 on Delta.

Which airlines fly non-stop between Chicago Midway Airport and Toronto?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago Midway Airport to Toronto.
There is just one airline that flies from Chicago Midway Airport to Toronto direct and that is Porter Airlines. The best one-way deal found from Porter Airlines for the route is $203.

How many flights are there between Chicago Midway Airport and Toronto per day?

Each day, there are between 2 and 3 nonstop flights that take off from Chicago Midway Airport and land in Toronto, with an average flight time of 1h 42m. The most common departure time is 5:00 pm and most flights take off in the morning, while the most flights land at Toronto Island Airport. Each week, there are 19 flights. The most frequent day of departure is Wednesday, when 16% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Chicago Midway Airport and Toronto?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago Midway Airport to Toronto take?

A direct flight to Toronto will take on average 1h 42m to travel the 443 miles flying distance from Chicago Midway Airport.

What’s the earliest departure time from Chicago Midway Airport to Toronto?

Early birds can take the earliest flight from Chicago Midway Airport at 8:00 am and will be landing in Toronto at 10:42 am.

What’s the latest departure time from Chicago Midway Airport to Toronto?

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Toronto jets off at 5:40 pm and lands at 8:22 pm.

Good to know

Low season

January

High season

May

Cheapest flight

$105
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Chicago Midway Airport to Toronto Island

When to book flights from Midway to Toronto

Are your dates flexible? Find out the best times to travel from Midway to Toronto 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 flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Toronto was $105 for a one-way ticket and $245 for a round-trip.

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

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

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Toronto?

    All the following airlines offer inflight Wi-Fi service on the Chicago Midway Airport to Toronto flight route: Air Canada, American Airlines, United Airlines, Breeze Airways, Delta, and British Airways.

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

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago Midway Airport to Toronto flight route.

  • On which days can I fly direct from Chicago Midway Airport to Toronto?

    There are nonstop flights from Chicago Midway Airport to Toronto on a daily basis.

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

    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.

  • 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?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Toronto 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?

    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 with an airline and back to Chicago Midway Airport with another airline.

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

    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 from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from Chicago to Toronto

  • Looking for a cheap flight? 25% of our users found flights on this route for $132 or less one-way and $266 or less round-trip.

Prefer to fly non-stop from Chicago Midway Airport to Toronto?

Find which airlines fly direct from Midway to Toronto, which days they fly and book direct flights.

Nonstop departures

Chicago Midway to Toronto

Monday

Porter Airlines

Porter Airlines

Tuesday

Porter Airlines

Porter Airlines

Wednesday

Porter Airlines

Porter Airlines

Thursday

Porter Airlines

Porter Airlines

Friday

Porter Airlines

Porter Airlines

Saturday

Porter Airlines

Porter Airlines

Sunday

Porter Airlines

Porter Airlines

See more direct flights

Nonstop returns

Toronto to Chicago Midway

Monday

Porter Airlines

Porter Airlines

Tuesday

Porter Airlines

Porter Airlines

Wednesday

Porter Airlines

Porter Airlines

Thursday

Porter Airlines

Porter Airlines

Friday

Porter Airlines

Porter Airlines

Saturday

Porter Airlines

Porter Airlines

Sunday

Porter Airlines

Porter Airlines

See more direct flights
See more direct flights

Top airline flying from Midway to Toronto

 
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 Toronto? 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.
7.4
Porter AirlinesOverall score based on 410 reviews
7.4Food
6.6Entertainment
8.2Crew
7.6Boarding
7.5Comfort
Airline reviews

Wish we had music during take off and landing like the last flight

10.0 ExcellentAnonymous, Apr 2024EWR - YTZ
Read more about Porter Airlines reviews

Wish we had music during take off and landing like the last flight

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Crew is ok. They offered food n drinks. Had difficulty connecting to wifi on board.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

Flight was smooth and comfortable. The crew were exceptional. Amanda, Nichole and Hershel were attentive to our every need. So friendly. My daughter and I were surprised at quality of service. Loved the double row seating. Snacks were delicious. We would definitely fly with Porter again. Flight PD 670 SFO to YYZ Thank you so much for the best flight experience we have had

The E195-E2 is a great aircraft! Leather seats, lots of legroom and SO quiet! The flight crew is terrific!

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

Flight delayed 6 hr. Looking for compensation and will claim for it.allow US people to fix to avoid huge delay having a canadian tech to fix it.

Book cheap flights from Chicago to Toronto

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Toronto found on KAYAK in the last 72 hours.
6/21Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
$105
6/6Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$107
6/6Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$111
6/19Wed
1 stopDelta
6h 34mMDW-YYZ
$132
7/18Thu
1 stopDelta
8h 29mMDW-YYZ
$137
6/11Tue
1 stopKLM
8h 04mMDW-YYZ
$138
6/1Sat
1 stop
12h 54mMDW-YYZ
$147
8/6Tue
1 stopWestJet
5h 13mMDW-YYZ
$154
9/20Fri
2 stopsWestJet
15h 10mMDW-YYZ
$156
6/3Mon
1 stop
25h 30mMDW-YYZ
$178

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Last minute flights from Midway to Toronto

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Toronto that are departing in the next 10 days.
5/27Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
5/29Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$459
5/27Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
5/29Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$463
5/23Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
5/30Thu
nonstopPorter Airlines
1h 47mYTZ-MDW
$502
5/24Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
5/28Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
$504
5/27Mon
multi-stopWestJet
5h 10mMDW-YYZ
5/29Wed
multi-stopWestJet
6h 37mYYZ-MDW
$538
5/25Sat
multi-stopWestJet
7h 12mMDW-YYZ
5/27Mon
multi-stopWestJet
9h 38mYYZ-MDW
$589
5/25Sat
nonstop
1h 42mMDW-YTZ
5/30Thu
multi-stop
23h 08mYTZ-MDW
$648
5/25Sat
multi-stopDelta
6h 37mMDW-YYZ
5/30Thu
multi-stopDelta
3h 55mYYZ-MDW
$662
5/24Fri
multi-stopDelta
7h 59mMDW-YYZ
5/26Sun
multi-stopDelta
5h 28mYYZ-MDW
$696
5/25Sat
nonstop
1h 42mMDW-YTZ
5/28Tue
multi-stop
28h 37mYTZ-MDW
$950

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Chicago Midway Airport - Toronto Flights

Departure:

Chicago Midway Airport (undefined)United States

Return flight deals:

Toronto - Chicago Midway Airport

Cabin classes:

$477
$159

Browse origins:

Browse destinations: