YTZ - MDW

$220 Find Cheap Flights from Toronto Island to Chicago - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$495
Typical prices: $209-$358
Multiple Airlines
Tue 12/11Fri 12/14
YTZ - MDW • 2 stops
Cheapest one-way
$220
Typical prices: $132-$246
Multiple Airlines
Sun 12/9
YTZ - MDW • 3 stops
When to book
25 weeks
in advance
Our data shows that travelers who book at least 25 weeks in advance save around 66% compared to booking last minute.
Insights
Insights
When to travel
January
Cheapest • 13% price drop
July
Most popular
Good to know
+1
Good to know
+1
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We hope you love your trip to Chicago Midway Airport!
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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

Fri, Dec 11 - Mon, Dec 14
Multiple Airlines Logo
7:10 pm - 11:33 amYTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
5:02 pm - 9:39 amMDW  Chicago Midway-YTZ Toronto Island
15h 37m2 stops Atlanta Hartsfield-Jackson Newark
$495Multiple Airlines
Mon, Dec 7 - Wed, Dec 16
Multiple Airlines Logo
7:10 pm - 11:33 amYTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:28 pm - 9:39 amMDW  Chicago Midway-YTZ Toronto Island
20h 11m2 stops Atlanta Hartsfield-Jackson Newark
$495Multiple Airlines
Tue, Dec 8 - Tue, Dec 15
Multiple Airlines Logo
9:10 am - 11:33 amYTZ  Toronto Island-MDW Chicago Midway
27h 23m2 stops Washington, D.C. Dulles Intl Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:28 pm - 1:34 pmMDW  Chicago Midway-YTZ Toronto Island
24h 06m2 stops Atlanta Hartsfield-Jackson Newark
$502Multiple Airlines
Mon, Dec 7 - Wed, Dec 9
Multiple Airlines Logo
7:10 pm - 11:33 amYTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:28 pm - 9:39 amMDW  Chicago Midway-YTZ Toronto Island
20h 11m2 stops Atlanta Hartsfield-Jackson Newark
$507Multiple Airlines
Wed, Dec 9 - Wed, Dec 16
Multiple Airlines Logo
7:10 pm - 4:06 pmYTZ  Toronto Island-MDW Chicago Midway
21h 56m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:28 pm - 11:19 amMDW  Chicago Midway-YTZ Toronto Island
21h 51m2 stops Atlanta Hartsfield-Jackson Newark
$509Multiple Airlines
Wed, Dec 9 - Wed, Dec 16
Multiple Airlines Logo
7:10 pm - 4:06 pmYTZ  Toronto Island-MDW Chicago Midway
21h 56m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:28 pm - 9:39 amMDW  Chicago Midway-YTZ Toronto Island
20h 11m2 stops Atlanta Hartsfield-Jackson Newark
$512Multiple Airlines
Tue, Dec 1 - Thu, Dec 3
Multiple Airlines Logo
7:10 pm - 11:33 amYTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
5:02 pm - 11:19 amMDW  Chicago Midway-YTZ Toronto Island
17h 17m2 stops Atlanta Hartsfield-Jackson Newark
$521Multiple Airlines
Fri, Dec 4 - Mon, Dec 7
Multiple Airlines Logo
7:10 pm - 11:33 amYTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
5:02 pm - 11:19 amMDW  Chicago Midway-YTZ Toronto Island
17h 17m2 stops Atlanta Hartsfield-Jackson Newark
$530Multiple Airlines
Mon, Dec 7 - Mon, Dec 14
Multiple Airlines Logo
7:10 pm - 11:33 amYTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
5:02 pm - 1:34 pmMDW  Chicago Midway-YTZ Toronto Island
19h 32m2 stops Atlanta Hartsfield-Jackson Newark
$541Multiple Airlines
Mon, Dec 7 - Wed, Dec 16
Multiple Airlines Logo
7:10 pm - 11:33 amYTZ  Toronto Island-MDW Chicago Midway
17h 23m2 stops Newark Atlanta Hartsfield-Jackson
Multiple Airlines Logo
10:40 am - 9:39 amMDW  Chicago Midway-YTZ Toronto Island
21h 59m3 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson Newark
$542Multiple 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 8% higher.

What’s 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 $230 round-trip.
•October ($307) and November ($301) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 33% 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 25 weeks before departure. Booking in this window typically costs about 66% 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

November

Cheapest flight

$220
Beat the crowds with an average 42% drop in travelers.
The most popular month to fly with an average 67% increase in travelers.
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.

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

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

  • 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 $209 to $358, with an average of $266 over the past 12 months. Anything below $209 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 $266 route average. Book 25 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 $30–$100 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 Embraer 175 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 $495 to $1,514. That means the highest observed fare was about 3x 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 $243, which is 32% 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 averaging $86 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 21% on flights from Toronto Island Airport to Chicago Midway Airport. Tuesday is the cheapest departure day at $229 round-trip on average, while Friday is the most expensive at $289, a difference of $60.

    KAYAK's flexible dates feature shows options up to 3 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.

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

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

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

    Only Porter Airlines currently offers free seat selection on this route. Availability depends on fare class.

  • Which airlines offer extra legroom on Toronto Island Airport to Chicago Midway Airport flights?

    None of the airlines on this route currently offer extra legroom.

  • 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 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 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 $229, about $60 less than Friday fares (21% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 25 weeks before you fly. On this route, that window historically saves about 66% 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 $230 round-trip in that month - typically $77 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