MDW - YTO

$136 Find Cheap Flights from Chicago Midway Airport to Toronto - Compare and Save

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Everything you should know

Cheapest round-trip
$342
Typical prices: $233-$398
Delta
Sat 1/13Fri 1/19
MDW - YYZ • 1 stop
Cheapest one-way
$136
Typical prices: $116-$260
Multiple Airlines
Sat 1/27
MDW - YYZ • 2 stops
Top routes
MDW - YTZ
Cheapest • 23% average savings
MDW - YYZ
Most popular
Insights
Insights
Avoid delays
Delta
Most punctual • 60% on-time
Night
Best time • Fewest delays
Insights
Insights
When to book
16 weeks
in advance
Our data shows that travelers who book at least 16 weeks in advance save around 63% compared to booking last minute.
Insights
Insights
When to travel
June
Cheapest • 13% price drop
June
Most popular
Good to know
+1
Good to know
+1
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Booking Insights
Expert advice
Flight Deals

Cheap Flights from Midway to Toronto (MDW-YTO)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Toronto

Wed, Jan 13 - Tue, Jan 19
Delta Logo
1:59 pm - 7:14 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
4h 15m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:45 am - 1:01 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 16m1 stop Detroit Metropolitan Wayne County
$342Delta
Mon, Dec 7 - Mon, Dec 14
Delta Logo
6:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 26m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 9:37 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
$342Delta
Fri, Dec 11 - Mon, Dec 14
Delta Logo
1:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
8h 26m1 stop Detroit Metropolitan Wayne County
Delta Logo
12:15 pm - 6:01 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
6h 46m1 stop Detroit Metropolitan Wayne County
$342Delta
Mon, Dec 7 - Fri, Dec 11
Delta Logo
6:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 26m1 stop Detroit Metropolitan Wayne County
Delta Logo
2:25 pm - 6:01 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 36m1 stop Detroit Metropolitan Wayne County
$342Delta
Fri, Jan 29 - Sun, Jan 31
Delta Logo
1:41 pm - 7:25 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
4h 44m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:10 am - 1:01 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
7h 51m1 stop Detroit Metropolitan Wayne County
$342Delta
Wed, Dec 2 - Fri, Dec 4
Delta Logo
6:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 26m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 9:37 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
$342Delta
Wed, Feb 10 - Tue, Feb 16
Delta Logo
1:41 pm - 10:59 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
8h 18m1 stop Detroit Metropolitan Wayne County
Delta Logo
12:07 pm - 6:08 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
7h 01m1 stop Detroit Metropolitan Wayne County
$342Delta
Mon, Nov 23 - Wed, Nov 25
Delta Logo
9:30 am - 1:30 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 00m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:45 am - 12:51 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 06m1 stop Detroit Metropolitan Wayne County
$342Delta
Thu, Dec 3 - Sun, Dec 6
Air France Logo
6:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 26m1 stop Detroit Metropolitan Wayne County
Air France Logo
2:25 pm - 6:01 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 36m1 stop Detroit Metropolitan Wayne County
$402Air France
Tue, Nov 24 - Sun, Nov 29
JetBlue Logo
9:36 am - 1:36 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 00m1 stop Detroit Metropolitan Wayne County
JetBlue Logo
12:21 pm - 6:10 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
6h 49m1 stop Detroit Metropolitan Wayne County
$412JetBlue
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Toronto flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Chicago Midway Airport to Toronto?

Round-trip flights from Chicago Midway Airport to Toronto typically range from $233 to $398. The lowest price found in the past 5 days was $342, on Delta.

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

Chicago Midway Airport (MDW) to Toronto Island Airport (YTZ) is the cheapest Chicago Midway Airport to Toronto route, averaging $285 round-trip. Other Chicago Midway Airport to Toronto routes average $452, based on KAYAK data over the past 12 months.

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

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Chicago Midway Airport to Toronto. It’s 11% cheaper than the average day, while Sunday is the most expensive, with prices 14% higher.

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

•June is the cheapest month to fly from Chicago Midway Airport to Toronto at $250 round-trip.
•February ($413) and November ($367) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 65% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago Midway Airport to Toronto the cheapest?

Flights from Chicago Midway Airport to Toronto are cheapest 16 weeks before departure. Booking in this window typically costs about 63% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Expert advice

Expert advice for your flight from Midway to Toronto

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Jennifer Bain

Jennifer Bain

Expert on YTZ

Jennifer Bain is a Canadian travel writer who takes at least 50 flights a year and has proudly visited all 13 of Canada's provinces and territories. She is a former newspaper travel editor who has written three travel books. Jennifer is the Canada editor for U.S.-based National Parks Traveler and freelances for numerous other outlets.

Read more

Key details for Chicago Midway Airport to Toronto flights

Low season

February

Cheapest flight

$136
Beat the crowds with an average 43% drop in travelers.
The most popular month to fly with an average 82% increase in travelers.
One-way flight from Chicago Midway Airport to Toronto Pearson Intl Airport

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

Your Chicago Midway Airport to Toronto flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Chicago Midway Airport to Toronto?

    Three cabin classes are available on flights from Chicago Midway Airport to Toronto:

    • Economy Class
    • Premium Economy Class
    • First Class

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

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Chicago Midway Airport to Toronto flight?

    Round-trip flights from Chicago Midway Airport to Toronto range from $233 to $398, with an average of $286 over the past 12 months. Anything below $233 counts as a good deal.

  • How expensive are last-minute Chicago Midway Airport to Toronto flights?

    Last-minute fares on this route (booked within two weeks of departure) run 75% above the $286 route average. Book 16 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Chicago Midway Airport to Toronto?

    On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $284 round-trip, compared to $396 via a layover through Detroit Metropolitan Wayne County (DTW).

  • How does on-time performance compare across airlines flying from Chicago Midway Airport to Toronto?

    Delta is the only airline operating Chicago Midway Airport to Toronto flights. 60% of its flights are on time.

  • What is the standard checked-bag allowance on flights from Chicago Midway Airport to Toronto?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $42–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Have flight prices from Chicago Midway Airport to Toronto changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $342 to $1,895. That means the highest observed fare was about 6x higher than the lowest one.

  • How are flight prices from Chicago Midway Airport to Toronto looking right now?

    One-way fares from Chicago Midway Airport to Toronto are currently lower than usual. Average one-way flight prices are about $150, which is 12% below the typical average for this route.

  • What car rental options are available in Toronto?

    Since Toronto is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Toronto Pearson Intl Airport (YYZ) — daily rates averaging $37:

    • Ace
    • City Car & Truck Rental
    • Routes Car & Truck Rentals
    • Zoom Rent A Car
    • Hertz

    Near Toronto Island Airport (YTZ) — daily rates averaging $55:

    • Hertz
    • Enterprise Rent-A-Car
    • National
    • Advance Car And Truck Rental
    • Zoom Rent A Car

  • Which airports can I use when flying from Chicago Midway Airport to Toronto?

    Flights from Chicago Midway Airport to Toronto usually depart from Chicago Midway (MDW) and may arrive at several airports in Toronto area, including Toronto Region of Waterloo Intl (YKF), Toronto Island (YTZ) and Toronto Pearson Intl (YYZ).

  • What time of day has the fewest delays on flights from Chicago Midway Airport to Toronto?

    Night flights have the fewest delays on this route, while afternoon departures tend to have the most.

  • At what point is a flight considered delayed from Chicago Midway Airport to Toronto?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago Midway Airport to Toronto route, 40% of flights were delayed in the past 3 months, with delays averaging 1h 18m.

  • Which airports do connecting flights from Chicago Midway Airport to Toronto pass through?

    Most connecting flights from Chicago Midway Airport to Toronto pass through Detroit Metropolitan Wayne County (DTW), which handles 100% of one-stop traffic on this route.

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to Toronto?

    Yes. Flexible dates can save you up to 23% on flights from Chicago Midway Airport to Toronto. Saturday is the cheapest departure day at $255 round-trip on average, while Sunday is the most expensive at $328, a difference of $73.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What is the time difference between Chicago Midway Airport and Toronto?

    Toronto is 1 hour ahead of Chicago Midway Airport (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Toronto?

    Some of the most popular sights in Toronto are Rogers Centre, Union Station and Scotiabank Arena. These are among the most viewed places in Toronto on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Chicago Midway Airport to Toronto flights?

    Among airlines operating Chicago Midway Airport to Toronto flights:

    • Porter Airlines: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago Midway Airport to Toronto flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Porter Airlines: a cabin bag and a checked bag in Economy Class
    • Air Transat: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Chicago Midway Airport to Toronto flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Saturday departure and avoid flying on Sunday. On this route, Saturday flights average $255, about $73 less than Sunday fares (22% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 16 weeks before you fly. On this route, that window historically saves about 63% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to Toronto trip for June. Fares historically average $250 round-trip in that month - typically $163 less than the most expensive month, which is February (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, hotels close to the airport you're flying into can be a convenient option.

    Near Toronto Pearson Intl Airport

    • Crowne Plaza Toronto Airport By IHG
    • Sheraton Gateway Hotel in Toronto International Airport
    • Spark by Hilton Toronto Airport

    Near Toronto Island Airport

    • The Omni King Edward Hotel
    • DoubleTree by Hilton Toronto Downtown
    • Hilton Toronto

More options for your flight from Midway to Toronto

Complete your trip to Toronto with a hotel stay or car rental

Car rentals in Toronto
Hotels in Toronto
Vacations in Toronto