MDW - YTZ

C$ 180 Find Cheap Flights from Chicago Midway Airport to Toronto Island – Compare and Save

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Everything you should know

Cheapest round-trip
C$ 605
Typical prices: C$ 329-C$ 563
Multiple Airlines
Sat 8/12Sat 15/12
MDW - YTZ • 2 stops
Cheapest one-way flights
C$ 180
Typical prices: C$ 161-C$ 376
Multiple Airlines
Sun 9/12
MDW - YTZ • 2 stops
When to book
16 weeks
in advance
Our data shows that travellers who book at least 16 weeks in advance save around 64% compared to booking last minute.
Insights
Insights
When to travel
April
Cheapest • 15% price drop
June
Most popular
Good to know
+1
Good to know
+1
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We hope you enjoy your trip to Toronto Island Airport!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Midway to Toronto Island (MDW-YTZ)

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

Recent round-trip flight deals from Midway to Toronto Island

Tue, 8 Dec - Tue, 15 Dec
Multiple Airlines Logo
12:28 p.m. - 9:39 a.m.MDW  Chicago Midway-YTZ Toronto Island
20h 11m2 stops Atlanta Hartsfield-Jackson Newark
Multiple Airlines Logo
9:10 a.m. - 9:45 a.m.YTZ  Toronto Island-MDW Chicago Midway
25h 35m2 stops Washington, D.C. Dulles Intl Dallas/Fort Worth
C$ 605Multiple Airlines
Fri, 11 Dec - Mon, 14 Dec
Multiple Airlines Logo
5:02 p.m. - 11:19 a.m.MDW  Chicago Midway-YTZ Toronto Island
17h 17m2 stops Atlanta Hartsfield-Jackson Newark
Multiple Airlines Logo
4:15 p.m. - 11:33 a.m.YTZ  Toronto Island-MDW Chicago Midway
20h 18m2 stops Washington, D.C. Dulles Intl Atlanta Hartsfield-Jackson
C$ 615Multiple Airlines
Wed, 9 Dec - Fri, 11 Dec
Multiple Airlines Logo
10:40 a.m. - 9:39 a.m.MDW  Chicago Midway-YTZ Toronto Island
21h 59m3 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson Newark
Multiple Airlines Logo
7:10 p.m. - 11:33 a.m.YTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
C$ 633Multiple Airlines
Thu, 19 Nov - Sun, 22 Nov
Multiple Airlines Logo
6:08 a.m. - 11:51 a.m.MDW  Chicago Midway-YTZ Toronto Island
28h 43m3 stops Atlanta Hartsfield-Jackson New York LaGuardia Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
9:50 a.m. - 8:14 a.m.YTZ  Toronto Island-MDW Chicago Midway
23h 24m3 stops Montreal Pierre Elliott Trudeau Intl Newark Atlanta Hartsfield-Jackson
C$ 698Multiple Airlines
Thu, 19 Nov - Sun, 22 Nov
Multiple Airlines Logo
6:08 a.m. - 11:51 a.m.MDW  Chicago Midway-YTZ Toronto Island
28h 43m3 stops Atlanta Hartsfield-Jackson New York LaGuardia Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
9:50 a.m. - 8:14 a.m.YTZ  Toronto Island-MDW Chicago Midway
23h 24m3 stops Montreal Pierre Elliott Trudeau Intl Newark Atlanta Hartsfield-Jackson
C$ 699Multiple Airlines
Thu, 19 Nov - Sun, 22 Nov
Multiple Airlines Logo
12:20 p.m. - 9:40 a.m.MDW  Chicago Midway-YTZ Toronto Island
20h 20m2 stops Dallas/Fort Worth New York LaGuardia
Multiple Airlines Logo
10:45 a.m. - 8:14 a.m.YTZ  Toronto Island-MDW Chicago Midway
22h 29m3 stops Montreal Pierre Elliott Trudeau Intl Newark Atlanta Hartsfield-Jackson
C$ 702Multiple Airlines
Thu, 19 Nov - Sun, 22 Nov
Multiple Airlines Logo
12:20 p.m. - 9:40 a.m.MDW  Chicago Midway-YTZ Toronto Island
20h 20m2 stops Dallas/Fort Worth New York LaGuardia
Multiple Airlines Logo
10:45 a.m. - 8:14 a.m.YTZ  Toronto Island-MDW Chicago Midway
22h 29m3 stops Montreal Pierre Elliott Trudeau Intl Newark Atlanta Hartsfield-Jackson
C$ 708Multiple Airlines
Fri, 11 Dec - Mon, 14 Dec
Multiple Airlines Logo
11:00 a.m. - 11:19 a.m.MDW  Chicago Midway-YTZ Toronto Island
23h 19m3 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson Newark
Multiple Airlines Logo
4:15 p.m. - 11:33 a.m.YTZ  Toronto Island-MDW Chicago Midway
20h 18m2 stops Washington, D.C. Dulles Intl Atlanta Hartsfield-Jackson
C$ 730Multiple Airlines
Thu, 3 Dec - Sun, 6 Dec
Multiple Airlines Logo
5:02 p.m. - 9:39 a.m.MDW  Chicago Midway-YTZ Toronto Island
15h 37m2 stops Atlanta Hartsfield-Jackson Newark
Multiple Airlines Logo
7:10 p.m. - 4:06 p.m.YTZ  Toronto Island-MDW Chicago Midway
21h 56m2 stops Newark Atlanta Hartsfield-Jackson
C$ 733Multiple Airlines
Tue, 8 Dec - Tue, 15 Dec
Multiple Airlines Logo
12:28 p.m. - 9:39 a.m.MDW  Chicago Midway-YTZ Toronto Island
20h 11m2 stops Atlanta Hartsfield-Jackson Newark
Multiple Airlines Logo
9:10 a.m. - 11:33 a.m.YTZ  Toronto Island-MDW Chicago Midway
27h 23m3 stops Washington, D.C. Dulles Intl Fort Lauderdale Atlanta Hartsfield-Jackson
C$ 744Multiple Airlines
Booking Insights

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

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

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

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 Island Airport. It's 8% cheaper than the average day, while Sunday is the most expensive, with prices 13% higher.

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

•April is the cheapest month to fly from Chicago Midway Airport to Toronto Island Airport at C$ 344 round-trip.
•January (C$ 508) and September (C$ 494) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 47% 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 Island Airport the cheapest?

Flights from Chicago Midway Airport to Toronto Island Airport are cheapest 16 weeks before departure. Booking in this window typically costs about 64% 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 Island

 
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 Island Airport flights

Low season

February

Cheapest flight

C$ 180
Beat the crowds with an average 45% drop in traveller numbers.
The most popular month to fly with an average 75% increase in traveller numbers.
One-way flight from Chicago Midway Airport to Toronto Island Airport

When to book flights from Midway to Toronto Island

Are your dates flexible? Find out the best times to travel from Midway to Toronto Island 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 Island Airport flight questions, answered

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

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

    Only Economy Class is available on flights from Chicago Midway Airport to Toronto Island Airport.

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

    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 Island Airport flight?

    Round-trip flights from Chicago Midway Airport to Toronto Island Airport range from C$ 329 to C$ 563, with an average of C$ 404 over the past 12 months. Anything below C$ 329 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 75% above the C$ 404 route average. Book 16 weeks before departure for the lowest fares.

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

    There is no standard. Checked bag policies vary by airline on this route. Most carriers charge C$ 59–C$ 140 for the first checked bag in economy. Premium fares and elite status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Chicago Midway Airport to Toronto Island Airport?

    The De Havilland (Bombardier) DHC-8-400 Dash 8Q family is used most often on this route, operated mainly by Porter Airlines and Air Transat. Other aircraft seen on the route include Embraer 175 variants.

  • Have flight prices from Chicago Midway Airport to Toronto Island Airport 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 C$ 605 to C$ 3,169. That means the highest observed fare was about 5x higher than the lowest one.

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

    One-way fares from Chicago Midway Airport to Toronto Island Airport are currently in line with typical prices for this route. Average one-way fares are about C$ 242.

  • What car rental options are available at Toronto Island Airport (YTZ)?

    Toronto Island Airport (YTZ) hosts 5 major car rental companies, with daily rates starting from around C$ 18 for economy cars. Top options include:

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

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

    Flights from Chicago Midway Airport to Toronto Island Airport usually depart from Chicago Midway (MDW) and arrive at Toronto Island (YTZ).

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

    Yes. Flexible dates can save you up to 19% on flights from Chicago Midway Airport to Toronto Island Airport. Saturday is the cheapest departure day at C$ 373 round-trip on average, while Sunday is the most expensive at C$ 460, a difference of C$ 87.

    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 Island Airport?

    Toronto Island Airport 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.

  • Which popular places can I visit in Toronto Island Airport?

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

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

    Among airlines operating Chicago Midway Airport to Toronto Island Airport 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 Island Airport flights?

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

    • Porter Airlines: a carry-on bag and a checked bag in Economy Class
    • Air Transat: a carry-on bag and a checked bag in Economy Class

    Baggage 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 Island Airport 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 C$ 373, about C$ 87 less than Sunday fares (19% 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 64% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to Toronto Island Airport trip for April. Fares historically average C$ 344 round-trip in that month – typically C$ 164 less than the most expensive month, which is January (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Toronto Island Airport.

    • The Omni King Edward Hotel
    • DoubleTree by Hilton Toronto Downtown
    • The Westin Harbour Castle, Toronto

More options for your flight from Midway to Toronto Island

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

Car rentals in Toronto
Hotels in Toronto
Vacations in Toronto