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$127+ Cheap flights from Toronto (YTO) 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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
Nov 5 — Nov 121
Tue 11/5
Tue 11/12
1 adult, Economy
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The best prices from Toronto to Chicago Midway are usually found in March or December, booked 24 days in advance, depart on a Saturday or Wednesday and return on a Monday

Cheap flight deals from Toronto to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Toronto (YTO) 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 October 31, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

February

Cheapest in

March

Round-trip from

$214
(Mytrip)

One-way from

$127
(Mytrip)
Provider with most accurate pricing for Toronto (YTO)-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago Midway flights.
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High demand for flights, 15% potential price rise
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Best time to find cheap flights, 16% potential price drop
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From Toronto (YTO) to Chicago Midway
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One-way flight from Toronto (YTO) to Chicago Midway
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Find flight deals from Toronto to Midway

Cheapest flights from Toronto to Midway
Explore the most affordable flight options available from Toronto to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 31, 2024.

This FlightHub deal was found by Cheapflights users on 10/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/279:30 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 12/412:05 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$225
This Flightnetwork deal was found by Cheapflights users on 10/30. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/213:50 pmYTZ - MDW
Nonstop1h 50mAir Transat
Sun 11/2411:15 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 10/30$246
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/412:15 pmYYZ - MDW
1 stop5h 47mDelta
Sat 12/75:50 pmMDW - YYZ
1 stop3h 46mDelta
Deal found 10/30$265
This FlightHub deal was found by Cheapflights users on 10/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/289:30 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Sat 11/3012:55 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 10/30$282
This FlightHub deal was found by Cheapflights users on 10/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/76:30 amYYZ - MDW
1 stop13h 02mWestJet
Tue 12/1012:44 pmMDW - YYZ
1 stop5h 22mWestJet
Deal found 10/31$305
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/86:06 pmYYZ - MDW
1 stop16h 53mMultiple Airlines
Mon 11/1110:32 pmMDW - YYZ
1 stop31h 14mMultiple Airlines
Deal found 10/30$488

Find flights from Toronto to Midway within your budget

Customize your flight search to find flights from Toronto 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 2,570,725 searches. Data last updated October 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/29

9:30 am-10:20 am

Nonstop1h 50m

$140

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 11/13

8:00 pm-7:55 am

1 stop12h 55m

$154

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 12/23

3:50 pm-4:40 pm

Nonstop1h 50m

$156

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 11/25

6:00 am-12:49 pm

1 stop7h 49m

$161

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 12/7

6:30 am-6:32 pm

1 stop13h 02m

$182

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 12/17

7:00 am-5:54 pm

2 stops11h 54m

$175

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 11/27

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Wed 12/4

12:05 pm-2:47 pm

Nonstop1h 42m

$225

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/21

3:50 pm-4:40 pm

Nonstop1h 50m

Chicago Midway

Sun 11/24

11:15 am-1:57 pm

Nonstop1h 42m

$246

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 12/4

12:15 pm-5:02 pm

1 stop5h 47m

Chicago Midway

Sat 12/7

5:50 pm-10:36 pm

1 stop3h 46m

$265

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/28

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Sat 11/30

12:55 pm-3:37 pm

Nonstop1h 42m

$282

Flights are sorted by cheapest first

Deals found on 10/30

Showing 1-10 of 11 results
1
2

Compare providers for flights from Toronto 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 to Midway in October.
ProviderPrice AccuracyTrust Score*Cancellation Policy
FlightHubPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
eDreamsPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy

*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-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-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto-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-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 to Midway

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

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

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

Use this chart to determine the optimal time to book a round-trip flight from Toronto to Midway. Price data was last updated on October 25, 2024.

The price you pay for your flight from Toronto to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 24 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Find deals

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

Currently, April is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of $159). Flying from Toronto to Chicago Midway Airport in July is currently the most expensive (average of $231). 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 YTO to MDW?

Find hourly flight availability from Toronto 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 October 31, 2024.

It’s optimal to fly from Toronto to Chicago Midway Airport at noon. By choosing this option you can save up to 16% on the cost of your flight, compared to a flight in the morning.

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 October 31, 2024.
Get a feel of what it's like to fly with Porter Airlines, Delta and Air Transat from Toronto to Chicago by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,835 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines
7.8
Good
294 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Transat
7.8
Good
388 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

WestJet
7.3
Good
2,804 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

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

  • Can I find flights from Toronto to Chicago Midway Airport for under $300 on Cheapflights?

    Yes, there are multiple flights from Toronto to Chicago Midway Airport for under $300. The cheapest flight booked recently is on Porter Airlines for just $214, but on average you can expect to pay $262.

  • Are there nonstop flights from Toronto to Chicago Midway Airport for under $300 on Cheapflights?

    Cheapflights has at least 3 direct flights from Toronto to Chicago Midway Airport under $300. A good price for a nonstop flight from Toronto to Chicago Midway Airport is less than $247.

  • Are there last-minute flights available from Toronto to Chicago Midway Airport for under $300?

    There are currently 6+ open flights from Toronto to Chicago Midway Airport within the next 7 days for less than $300.

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

    Our cheapest airline available from Toronto to Chicago Midway Airport is Porter Airlines. Our recent data shows that you can find tickets from as low as $214 on this airline. Additional options worth looking into are Air Transat and Delta, starting at $246 and $265 round-trip. Porter Airlines is 17% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Toronto to Chicago Midway Airport one-way?

    $127 is the cheapest one-way deal found within the past few days, from Porter Airlines. You may also be able to find cheap deals on Air Transat and Delta, with prices starting from $156 and $161, respectively.

  • What does YYZ to MDW mean?

    YYZ and MDW are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. YYZ to MDW refers to a flight route from Toronto Pearson Intl Airport to Chicago Midway Airport. Toronto Island Airport (YTZ), Hamilton Airport (YHM), Toronto Region of Waterloo Intl Airport (YKF) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Toronto to Midway that include extra baggage allowance?

    The amount of baggage you can bring on your Toronto to Midway flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Toronto to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Toronto to Midway flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Toronto 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.

  • Can I find deals for flights from Toronto to Midway that allow pets onboard?

    Many airlines flying from Toronto to Midway offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Toronto to Midway?

    Yes, you can often find last-minute deals on Toronto to Midway flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Toronto to Chicago Midway Airport flight deals updated?

    The Toronto to Chicago Midway Airport flight deals you see on this page were last updated on 10/31.

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

    Currently, April is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of $159). Flying from Toronto to Chicago Midway Airport in July is currently the most expensive (average of $231). 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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Top airline flying from Toronto to Midway

Discover the top airline that operate flights from Toronto 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 2,570,725 searches. Data last updated October 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$205Average$256FlexibilityNo cancel feeOn-time52%
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