YTZ - MDW

C$ 265 Find Cheap Flights from Toronto Island to Chicago Midway Airport – Compare and Save

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Everything you should know

Cheapest round-trip
C$ 536
Typical prices: C$ 292-C$ 502
Multiple Airlines
Sun 11/11Wed 14/11
YTZ - MDW • 2 stops
Cheapest one-way flights
C$ 265
Typical prices: C$ 185-C$ 341
Multiple Airlines
Sat 17/11
YTZ - MDW • 2 stops
When to book
26 weeks
in advance
Our data shows that travellers who book at least 26 weeks in advance save around 70% compared to booking last minute.
Insights
Insights
When to travel
January
Cheapest • 14% price drop
July
Most popular
Good to know
+1
Good to know
+1
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We hope you enjoy your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Flight Deals

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

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

Recent round-trip flight deals from Toronto Island to Midway

Wed, 11 Nov - Sat, 14 Nov
Multiple Airlines Logo
9:10 a.m. - 11:47 p.m.YTZ  Toronto Island-MDW Chicago Midway
15h 37m2 stops Washington, D.C. Dulles Intl Atlanta Hartsfield-Jackson
Multiple Airlines Logo
7:15 a.m. - 12:50 p.m.MDW  Chicago Midway-YTZ Toronto Island
28h 35m2 stops Atlanta Hartsfield-Jackson Washington, D.C. Dulles Intl
C$ 536Multiple Airlines
Fri, 4 Dec - Sun, 6 Dec
Multiple Airlines Logo
7:10 p.m. - 11:33 a.m.YTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
5:02 p.m. - 11:19 a.m.MDW  Chicago Midway-YTZ Toronto Island
17h 17m2 stops Atlanta Hartsfield-Jackson Newark
C$ 574Multiple Airlines
Mon, 7 Dec - Mon, 14 Dec
Multiple Airlines Logo
7:10 p.m. - 11:33 a.m.YTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
5:02 p.m. - 1:34 p.m.MDW  Chicago Midway-YTZ Toronto Island
19h 32m2 stops Atlanta Hartsfield-Jackson Newark
C$ 577Multiple Airlines
Fri, 4 Dec - Fri, 11 Dec
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
Multiple Airlines Logo
11:00 a.m. - 6:15 p.m.MDW  Chicago Midway-YTZ Toronto Island
30h 15m3 stops Dallas/Fort Worth Denver Intl Nashville Intl
C$ 583Multiple Airlines
Mon, 7 Dec - Wed, 9 Dec
Multiple Airlines Logo
7:10 p.m. - 11:33 a.m.YTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:28 p.m. - 11:19 a.m.MDW  Chicago Midway-YTZ Toronto Island
21h 51m2 stops Atlanta Hartsfield-Jackson Newark
C$ 585Multiple Airlines
Tue, 1 Dec - Tue, 8 Dec
Multiple Airlines Logo
7:10 p.m. - 11:33 a.m.YTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:28 p.m. - 11:19 a.m.MDW  Chicago Midway-YTZ Toronto Island
21h 51m2 stops Atlanta Hartsfield-Jackson Newark
C$ 595Multiple Airlines
Tue, 8 Dec - Tue, 15 Dec
Multiple Airlines Logo
7:10 p.m. - 11:33 a.m.YTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:28 p.m. - 9:39 a.m.MDW  Chicago Midway-YTZ Toronto Island
20h 11m2 stops Atlanta Hartsfield-Jackson Newark
C$ 599Multiple Airlines
Tue, 1 Dec - Wed, 9 Dec
Multiple Airlines Logo
4:30 p.m. - 11:33 a.m.YTZ  Toronto Island-MDW Chicago Midway
20h 03m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:28 p.m. - 9:39 a.m.MDW  Chicago Midway-YTZ Toronto Island
20h 11m2 stops Atlanta Hartsfield-Jackson Newark
C$ 602Multiple Airlines
Tue, 1 Dec - Tue, 8 Dec
Multiple Airlines Logo
7:10 p.m. - 11:33 a.m.YTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:28 p.m. - 9:39 a.m.MDW  Chicago Midway-YTZ Toronto Island
20h 11m2 stops Atlanta Hartsfield-Jackson Newark
C$ 604Multiple Airlines
Thu, 19 Nov - Mon, 23 Nov
Multiple Airlines Logo
7:10 p.m. - 11:55 a.m.YTZ  Toronto Island-MDW Chicago Midway
17h 45m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
9:09 a.m. - 7:55 p.m.MDW  Chicago Midway-YTZ Toronto Island
9h 46m2 stops Atlanta Hartsfield-Jackson Washington, D.C. Dulles Intl
C$ 609Multiple Airlines
Booking Insights

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

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Toronto Island Airport to Chicago Midway Airport. It’s 14% cheaper than the average day, while Friday is the most expensive, with prices 6% higher.

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

•January is the cheapest month to fly from Toronto Island Airport to Chicago Midway Airport at C$ 321 round-trip.
•October (C$ 469) and May (C$ 408) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 46% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

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

Flights from Toronto Island Airport to Chicago Midway Airport are cheapest 26 weeks before departure. Booking in this window typically costs about 70% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Key details for Toronto Island Airport to Chicago Midway Airport flights

Low season

February

Cheapest flight

C$ 265
Beat the crowds with an average 41% drop in traveller numbers.
The most popular month to fly with an average 59% increase in traveller numbers.
One-way flight from Toronto Island Airport to Chicago Midway Airport

When to book flights from Toronto Island to Midway

Are your dates flexible? Find out the best times to travel from Toronto Island to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Toronto Island Airport to Chicago Midway 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 Toronto Island Airport to Chicago Midway Airport?

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

    • Economy Class
    • Premium Economy Class

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

    Round-trip flights from Toronto Island Airport to Chicago Midway Airport range from C$ 292 to C$ 502, with an average of C$ 371 over the past 12 months. Anything below C$ 292 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 59% above the C$ 371 route average. Book 26 weeks before departure for the lowest fares.

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

    There is no standard. Checked bag policies vary by airline on this route. Most carriers charge C$ 41–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 Toronto Island Airport to Chicago Midway 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 Boeing 737 MAX 8 variants.

  • Have flight prices from Toronto Island Airport to Chicago Midway 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$ 536 to C$ 2,851. That means the highest observed fare was about 5x higher than the lowest one.

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

    One-way fares from Toronto Island Airport to Chicago Midway Airport are currently higher than usual. Average one-way flight prices are about C$ 277, which is 10% above the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around C$ 45 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

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

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

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

    Yes. Flexible dates can save you up to 19% on flights from Toronto Island Airport to Chicago Midway Airport. Tuesday is the cheapest departure day at C$ 322 round-trip on average, while Friday is the most expensive at C$ 396, a difference of C$ 74.

    KAYAK's flexible dates feature shows options up to three days before and after your selected dates, making it easier to compare nearby fares.

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

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

  • Which popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, River North, and Grant Park. These are among the most viewed places in Chicago Midway Airport on KAYAK.

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

    Among airlines operating Toronto Island Airport to Chicago Midway 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 Toronto Island Airport to Chicago Midway 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 Toronto Island Airport to Chicago Midway 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 Tuesday departure and avoid flying on Friday. On this route, Tuesday flights average C$ 322, about C$ 74 less than Friday fares (19% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 26 weeks before you fly. On this route, that window historically saves about 70% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Toronto Island Airport to Chicago Midway Airport trip for January. Fares historically average C$ 321 round-trip in that month – typically C$ 148 less than the most expensive month, which is October (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel

More options for your flight from Toronto Island to Midway

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

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago