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$144+ Cheap flights from Toronto Island (YTZ) to Midway (MDW)

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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — MDW
Dec 7 — Dec 141
Sat 12/7
Sat 12/14
1 adult, Economy
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The best prices from Toronto Island to Chicago Midway are usually found in January or December, booked 90 days in advance, depart on a Tuesday or Friday and return on a Tuesday

Cheap flight deals from Toronto Island to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Toronto Island (YTZ) to Midway (MDW). 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 December 2, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

November

Cheapest in

January

Round-trip from

$228
(Kiwi.com)

One-way from

$144
(Porter Airlines)
Provider with most accurate pricing for Toronto Island-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Toronto Island-Chicago Midway flights.
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High demand for flights, 11% potential price rise
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Best time to find cheap flights, 19% potential price drop
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From Toronto Island to Chicago Midway
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One-way flight from Toronto Island to Chicago Midway
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Find flight deals from Toronto Island to Midway

Cheapest flights from Toronto Island to Midway
Explore the most affordable flight options available from Toronto Island to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 2, 2024.

This oojo deal was found by Cheapflights users on 12/2. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/199:40 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 1/45:35 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/2$237
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/199:40 amYTZ - MDW
Nonstop1h 50mAir Transat
Sat 1/45:35 pmMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 12/1$293
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/1411:10 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Sun 12/155:15 amMDW - YTZ
2 stops12h 38mMultiple Airlines
Deal found 12/1$342

Find flights from Toronto Island to Midway within your budget

Customize your flight search to find flights from Toronto Island to Midway 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 2,650,959 searches. Data last updated December 2, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 2/20

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

Sun 2/23

1:05 pm-3:47 pm

Nonstop1h 42m

$228

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/9

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

Sun 1/12

1:05 pm-3:47 pm

Nonstop1h 42m

$246

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/24

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

Fri 1/31

1:05 pm-3:47 pm

Nonstop1h 42m

$254

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 2/12

11:20 am-12:10 pm

Nonstop1h 50m

$144

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 3/29

11:10 am-12:00 pm

Nonstop1h 50m

$179

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/17

11:20 am-6:01 pm

1 stop7h 41m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

Compare providers for flights from Toronto Island to Midway

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 Toronto Island to Midway in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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 Toronto Island Airport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toronto Island Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto Island Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto Island Airport-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub 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 Toronto Island Airport-Chicago Midway 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 Toronto Island to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Toronto Island 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.

Travel insights for flights from Toronto Island to Midway

Get recent, data-driven insights about flights from Toronto Island to Midway including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Toronto Island Airport to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Toronto Island to Midway. Price data was last updated on November 22, 2024.

Booking 89 days in advance of your planned departure date is, on average, the best time to get cheap flights from Toronto Island Airport to Chicago Midway Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, April is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of $160). Flying from Toronto Island Airport to Chicago Midway Airport in October is currently the most expensive (average of $232). 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 YTZ to MDW?

Find hourly flight availability from Toronto Island to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 2, 2024.

When flying from Toronto Island Airport to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 4% versus a flight in the morning.

Weekly flight availability from Toronto Island Airport to Chicago Midway Airport

Explore weekly flight availability from Toronto Island to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 2, 2024.

The most flights from YTZ to MDW are scheduled on a Friday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated December 2, 2024.
Read reviews from past customers who have flown Porter Airlines and Air Transat from Toronto to Chicago. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.8
Good
286 reviews

Boarding

8.1

Food

7.6

Crew

8.7

Overall

7.8

Entertainment

6.9

Comfort

8.0

Reviews

1 / 10

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

Porter Airlines
7.8
Good
286 reviews
Porter Airlines
7.8
Good
286 reviews

Boarding

8.1

Food

7.6

Crew

8.7

Overall

7.8

Entertainment

6.9

Comfort

8.0

Reviews

1 / 10

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

Air Transat
7.8
Good
391 reviews
Porter Airlines
7.8
Good
286 reviews

Boarding

8.1

Food

7.6

Crew

8.7

Overall

7.8

Entertainment

6.9

Comfort

8.0

Reviews

1 / 10

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

Related info for your journey

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

  • What are the cheapest airlines flying from Toronto Island Airport to Chicago Midway Airport round-trip?

    Porter Airlines, at $228, was found to be the cheapest airline from Toronto Island Airport to Chicago Midway Airport. An alternate airline flying to your destination would be Air Transat. Porter Airlines is currently priced 11% below the average price you’ll pay for this route.

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

    The top 3 most reliable airlines when flying from Toronto Island Airport to Chicago Midway Airport are Air Transat (88%), Porter Airlines (88%) and Porter Airlines (88%).

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

    The cheapest flight price from Toronto Island Airport to Chicago Midway Airport is $135. On average you can expect to pay $254. The most popular route, (Toronto Island - Chicago Midway), can usually be booked for $202.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Toronto Island to Midway 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 Toronto Island Airport to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago Midway Airport (average of $160). Flying from Toronto Island Airport to Chicago Midway Airport in October is currently the most expensive (average of $232). 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.

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Alternative routes for Toronto Island to Midway

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

Top airline flying from Toronto Island to Midway

Discover the top airline that operate flights from Toronto Island to Midway. 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 2,650,959 searches. Data last updated December 2, 2024.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$205Average$254FlexibilityNo cancel feeOn-time52%
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