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Toronto Island

$85+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YTZ
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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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 October 27, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/54:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 12/79:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/27$190
This Trip.com deal was found by Cheapflights users on 10/25. 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.
Sat 11/1512:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 11/172:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/25$191
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/1311:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 11/169:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/27$192
This Trip.com deal was found by Cheapflights users on 10/26. 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 11/1211:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 11/2211:00 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/26$197
This Trip.com deal was found by Cheapflights users on 10/26. 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.
Mon 11/104:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 11/119:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/26$198
This Trip.com deal was found by Cheapflights users on 10/27. 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.
Fri 12/54:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 12/89:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/27$214
This SmartFares deal was found by Cheapflights users on 10/25. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/144:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 11/189:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/25$215

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 October 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$191
(Trip.com)

One-way from

$85
(Trip.com)

Popular in

March

Cheapest in

July

Average price

$407

Good round-trip deal

$257 or less

Good one-way deal

$186 or less
Provider with most accurate pricing for Chicago Midway-Toronto Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Toronto Island flights.
Search Deals
From Chicago Midway to Toronto Island
Search Deals
One-way flight from Chicago Midway to Toronto Island
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Toronto Island.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Toronto Island.
Search Deals

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 October 27, 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

Thu 11/13

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 11/16

9:15 am-10:05 am

Nonstop1h 50m

$192

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 11/15

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Mon 11/17

9:15 am-10:05 am

Nonstop1h 50m

$197

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 2/20

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Wed 2/25

9:15 am-10:05 am

Nonstop1h 50m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 3/21

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Sun 3/22

9:15 am-10:05 am

Nonstop1h 50m

$211

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 11/14

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Sun 11/16

9:15 am-10:05 am

Nonstop1h 50m

$216

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 2/21

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Sun 2/22

2:30 pm-3:20 pm

Nonstop1h 50m

$217

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 11/20

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Sun 11/23

2:30 pm-3:20 pm

Nonstop1h 50m

$223

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 12/6

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Sun 12/7

9:15 am-10:05 am

Nonstop1h 50m

$231

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 11/13

4:15 pm-6:57 pm

Nonstop1h 42m

$85

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 11/10

4:15 pm-6:57 pm

Nonstop1h 42m

$85

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

Showing 1-10 of 16 results
1
2

Compare providers for flights from Midway to Toronto Island

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Toronto Island in October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Toronto Island Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Toronto Island Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Toronto Island Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Toronto Island Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Toronto Island Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 month to book a flight from Chicago Midway Airport to Toronto Island Airport?

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto Island Airport (average of $135). Flying from Chicago Midway Airport to Toronto Island Airport in March is currently the most expensive (average of $473). 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.

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 October 27, 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 13% 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 October 27, 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
8.0
Very good
384 reviews

Food

7.6

Comfort

8.0

Entertainment

7.0

Overall

8.0

Boarding

8.2

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
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews

Food

7.6

Comfort

8.0

Entertainment

7.0

Overall

8.0

Boarding

8.2

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 $185. Users have found that Porter Airlines is 34% 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 (87%), Air Transat (87%), Porter Airlines (87%).

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

    Looking at all options, your cheapest flight can be booked for $77. While the most popular route (Chicago Midway - Toronto Island) can be booked for $141 on average, our data indicates $292 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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Toronto Island Airport (average of $135). Flying from Chicago Midway Airport to Toronto Island Airport in March is currently the most expensive (average of $473). 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
O'Hare Intl to Toronto Island flights
Midway to Pearson Intl 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 October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$185Average$234FlexibilityNo cancel feeOn-time52%

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