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$139+ Cheap flights from Pearson Intl (YYZ) 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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
1 adult, Economy
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Cheap flight deals from Pearson Intl to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Pearson Intl (YYZ) 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 March 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$223
(Delta)

One-way from

$139
(Delta)

Popular in

April

Cheapest in

February

Average price

$281
Provider with most accurate pricing for Toronto Pearson Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Toronto Pearson Intl-Chicago Midway flights.
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From Toronto Pearson Intl to Chicago Midway
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One-way flight from Toronto Pearson Intl to Chicago Midway
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Highest demand for flights based on searches. 7% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Find flight deals from Pearson Intl to Midway

Cheapest flights from Pearson Intl to Midway
Explore the most affordable flight options available from Pearson Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2025.

This Delta deal was found by Cheapflights users on 3/24. 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.
Tue 5/612:54 pmYYZ - MDW
1 stop5h 25mDelta
Wed 5/76:25 pmMDW - YYZ
1 stop3h 33mDelta
Deal found 3/24$223
This CheapTicketsDeal deal was found by Cheapflights users on 3/25. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/27:21 pmYYZ - MDW
1 stop22h 58mWestJet
Mon 5/57:00 pmMDW - YYZ
1 stop15h 59mWestJet
Deal found 3/25$280
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Sun 4/66:30 amYYZ - MDW
2 stops23h 50mMultiple Airlines
Wed 4/912:46 pmMDW - YYZ
1 stop29h 44mMultiple Airlines
Deal found 3/24$326

Cheapflights Fare Finder

Customize your flight search to find flights from Pearson Intl 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 2,558,603 searches. Data last updated March 26, 2025.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Pearson Intl

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 5/6

12:54 pm-5:19 pm

1 stop5h 25m

Chicago Midway

Wed 5/7

6:25 pm-10:58 pm

1 stop3h 33m

$223

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 5/2

7:21 pm-5:19 pm

1 stop22h 58m

Chicago Midway

Mon 5/5

7:00 pm-11:59 am

1 stop15h 59m

$280

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 4/6

6:30 am-5:20 am

2 stops23h 50m

Chicago Midway

Wed 4/9

12:46 pm-7:30 pm

1 stop29h 44m

$326

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 4/23

12:54 pm-5:19 pm

1 stop5h 25m

$139

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 4/2

2:00 pm-11:43 am

2 stops22h 43m

$154

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/26

12:54 pm-5:19 pm

1 stop5h 25m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

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

Have a flexible travel schedule? Discover the best time to fly to Midway from Pearson Intl 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 Toronto Pearson Intl Airport to Chicago Midway Airport

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

Currently, April is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of $160). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

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 March 26, 2025.
See what other customers who have flown with Delta and WestJet from Toronto to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,891 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,891 reviews
Delta
8.0
Very good
7,891 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,785 reviews
Delta
8.0
Very good
7,891 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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 Pearson Intl 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 Pearson Intl Airport to Chicago Midway Airport round-trip?

    Delta, at $223, was found to be the cheapest airline from Toronto Pearson Intl Airport to Chicago Midway Airport. An alternate airline flying to your destination would be WestJet. Delta is 34% cheaper than the average price of flights available within the next 90 days to this destination.

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

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

  • How can I find direct flights from Pearson Intl to Midway?

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

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

    Yes. Cheapflights offers flight deals from Pearson Intl 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 Pearson Intl Airport to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of $160). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Toronto Pearson Intl Airport?

Book flights to Toronto Pearson Intl Airport if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Pearson Intl to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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