YTZ - MDW

$143 Find Cheap Flights from Toronto Island to Chicago - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$207
Typical prices: $206-$347
Porter Airlines
Fri 10/12Mon 10/15
YTZ - MDW • Non-stop
Cheapest one-way
$128
Typical prices: $132-$237
Porter Airlines
Sat 10/13
YTZ - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Porter Airlines. Average duration is 1h 50m
Direct flights
+1
Direct flights
+1
When to book
26 weeks
in advance
Our data shows that travelers who book at least 26 weeks in advance save around 70% compared to booking last minute.
Insights
Insights
When to travel
September
Cheapest • 14% price drop
June
Most popular
Good to know
+1
Good to know
+1
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We hope you love 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

Thu, Oct 15 - Fri, Oct 16
Air Transat Logo
10:10 am - 11:00 amYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Air Transat Logo
3:20 pm - 6:00 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$217Air Transat
Tue, Oct 20 - Wed, Oct 21
Air Transat Logo
10:10 am - 11:00 amYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Air Transat Logo
11:45 am - 2:25 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$217Air Transat
Wed, Oct 14 - Thu, Oct 15
Air Transat Logo
10:10 am - 11:00 amYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Air Transat Logo
11:45 am - 2:25 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$217Air Transat
Thu, Oct 15 - Sun, Oct 18
Air Transat Logo
10:10 am - 11:00 amYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Air Transat Logo
11:45 am - 2:25 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$217Air Transat
Wed, Oct 14 - Tue, Oct 20
Air Transat Logo
1:45 pm - 2:35 pmYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Air Transat Logo
11:45 am - 2:25 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$220Air Transat
Mon, Oct 19 - Wed, Oct 21
Air Transat Logo
10:10 am - 11:00 amYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Air Transat Logo
11:45 am - 2:25 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$226Air Transat
Fri, Oct 16 - Fri, Oct 16
Air Transat Logo
10:10 am - 11:00 amYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Air Transat Logo
3:20 pm - 6:00 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$227Air Transat
Thu, Oct 15 - Sun, Oct 18
Air Transat Logo
10:10 am - 11:00 amYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Air Transat Logo
11:45 am - 2:25 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$236Air Transat
Fri, Oct 23 - Fri, Oct 23
Porter Airlines Logo
10:10 am - 11:00 amYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$289Porter Airlines
Tue, Oct 13 - Tue, Oct 20
Porter Airlines Logo
1:45 pm - 2:35 pmYTZ  Toronto Island-MDW Chicago Midway
1h 50mnonstop
Porter Airlines Logo
11:45 am - 2:25 pmMDW  Chicago Midway-YTZ Toronto Island
1h 40mnonstop
$326Porter 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.

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

Round-trip flights from Toronto Island Airport to Chicago Midway Airport typically range from $206 to $347. The lowest price found in the past 5 days was $207, on Porter Airlines.

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, Monday is the cheapest day of the week to fly from Toronto Island Airport to Chicago Midway Airport. It’s 7% cheaper than the average day, while Sunday is the most expensive, with prices 5% higher.

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

•September is the cheapest month to fly from Toronto Island Airport to Chicago Midway Airport at $222 round-trip.
•August ($293) and May ($292) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 31% 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.

Find deals

Key details for Toronto Island Airport to Chicago Midway Airport flights

Low season

February

Cheapest flight

$128
Beat the crowds with an average 53% drop in travelers.
The most popular month to fly with an average 31% 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 are the earliest and latest flights from Toronto Island Airport to Chicago Midway Airport?

    These are the earliest and latest flight times available from Toronto Island Airport to Chicago Midway Airport:

    • Earliest: departs at 10:10 am and lands at 12:00 pm
    • Latest: departs at 1:45 pm and lands at 3:35 pm.

    The flight takes about 1h 50m.

  • 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.

  • How long is a flight from Toronto Island Airport to Chicago Midway Airport?

    A nonstop flight from Toronto Island Airport to Chicago Midway Airport takes 1h 50m, covering 442 miles.

  • 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 $206 to $347, with an average of $259 over the past 12 months. Anything below $206 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 63% above the $259 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 $26–$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 Boeing 737-900 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 $217 to $894. That means the highest observed fare was about 4x 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 lower than usual. Average one-way flight prices are about $136, which is 24% below 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 $32 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 12% on flights from Toronto Island Airport to Chicago Midway Airport. Monday is the cheapest departure day at $243 round-trip on average, while Sunday is the most expensive at $274, a difference of $31.

    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 airlines fly from Toronto Island Airport to Chicago Midway Airport?

    Only Porter Airlines operates flights between Toronto Island Airport and Chicago Midway Airport.

  • 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 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 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 Monday departure and avoid flying on Sunday. On this route, Monday flights average $243, about $31 less than Sunday fares (11% 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 September. Fares historically average $222 round-trip in that month - typically $71 less than the most expensive month, which is August (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

Prefer to fly direct from Toronto Island to Chicago?

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

Direct departures

Toronto Island 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

Direct returns

Chicago Midway to Toronto Island

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

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