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Toronto Island

$75+ Cheap flights from Midway (MDW) to Toronto Island (YTZ)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YTZ
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Midway to Toronto Island

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Toronto Island (YTZ). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$171
(Kiwi.com)

One-way from

$75
(Trip.com)

Popular in

September

Cheapest in

June

Average price

$392

Good round-trip deal

$201 or less

Good one-way deal

$90 or less
From Chicago Midway to Toronto Island
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One-way flight from Chicago Midway to Toronto Island
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Highest demand for flights based on searches. 14% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to Toronto Island.
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Price to beat on a one-way flight from Chicago Midway to Toronto Island.
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Find flight deals from Midway to Toronto Island

Cheapest flights from Midway to Toronto Island
Explore the most affordable flight options available from Midway to Toronto Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/49:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 10/87:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/10$171
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/145:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 10/177:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/9$173
This Trip.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/129:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 10/197:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/9$178
This Trip.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/304:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 11/22:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 9/10$179
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/119:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 10/143:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/9$195
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 10/197:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/10$200
This Trip.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/85:20 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Sat 10/187:50 amYTZ - MDW
Nonstop1h 49mMultiple Airlines
Deal found 9/10$206
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/204:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 11/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 9/10$213
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/194:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 11/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 9/10$215
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/29:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 10/57:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/10$218
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2212:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 11/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 9/10$219
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/611:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 11/102:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 9/10$220

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Toronto Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Toronto Island Airport that are best for you.

Fly from

Midway

Fly to

Toronto Island

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 10/4

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Wed 10/8

7:50 am-8:39 am

Nonstop1h 49m

$171

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 10/31

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Mon 11/3

9:15 am-10:05 am

Nonstop1h 50m

$171

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 10/15

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Wed 10/22

7:50 am-8:39 am

Nonstop1h 49m

$173

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 10/19

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Fri 10/24

3:35 pm-4:24 pm

Nonstop1h 49m

$173

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 10/2

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 10/5

7:50 am-8:39 am

Nonstop1h 49m

$173

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 10/23

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Sun 10/26

9:15 am-10:05 am

Nonstop1h 50m

$177

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 10/5

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Tue 10/7

7:50 am-8:39 am

Nonstop1h 49m

$190

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 10/11

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sat 10/18

7:50 am-8:39 am

Nonstop1h 49m

$190

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 10/14

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Wed 10/15

7:50 am-8:39 am

Nonstop1h 49m

$195

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 10/4

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 10/5

7:50 am-8:39 am

Nonstop1h 49m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 20 results
1
2

Best time to book a flight from Midway to Toronto Island

Have a flexible travel schedule? Discover the best time to fly to Toronto Island from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Toronto Island Airport

What is the cheapest time of day to fly from MDW to YTZ?

Find hourly flight availability from Midway to Toronto Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Toronto Island Airport in the afternoon. If you’re flexible enough to do this you can expect to save up to 12% on your trip compared to booking a flight at noon.

Reviews of airlines servicing Toronto Island

Get insights into the airlines that provide service to Toronto Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Toronto Island. Reviews last updated September 11, 2025.
See what other customers who have flown with Porter Airlines from Chicago Midway Airport to Toronto Island Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

Related info for your journey

Find useful and relevant information for your journey from Midway to Toronto Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Porter Airlines can get you from Chicago Midway Airport to Toronto Island Airport in just under 1h 42m. Your travel time will be generally consistent. The distance from Chicago Midway Airport to Toronto Island Airport is about 442 mi. Most flights are nonstop.

  • What is the cheapest airline to fly from Chicago Midway Airport to Toronto Island Airport round-trip?

    Cheapflights users have booked flights from Chicago Midway Airport to Toronto Island Airport round-trip from $187. Users have found that Porter Airlines is 32% cheaper than the other options available to this destination.

  • What are the most reliable airlines from Chicago Midway Airport to Toronto Island Airport?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago Midway Airport to Toronto Island Airport on time: Porter Airlines (83%), Air Transat (83%), Porter Airlines (83%).

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

    Looking at all options, your cheapest flight can be booked for $69. While the most popular route (Chicago Midway - Toronto Island) can be booked for $171 on average, our data indicates $204 when flying from Chicago Midway Airport to Toronto Island Airport.

  • Can I find deals for flights from Midway to Toronto Island that include hotel bookings?

    Yes. In addition to deals on Midway to Toronto Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Toronto Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Toronto Island.

  • Can I find deals for business class flights from Midway to Toronto Island?

    Yes. Cheapflights offers flight deals from Midway to Toronto Island by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Toronto Island Airport?

    Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto Island Airport (average of $228). Flying from Chicago Midway Airport to Toronto Island Airport in November is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midway to Toronto Island

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Pearson Intl flights
Midway to Pearson Intl flights
O'Hare Intl to Toronto Island flights
O'Hare Intl to Hamilton flights

Top airline flying from Midway to Toronto Island

Discover the top airline that operate flights from Midway to Toronto Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$187Average$258FlexibilityNo cancel feeOn-time52%

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