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$136+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$244
(CheapTicketsDeal)

One-way from

$136
(Kiwi.com)

Popular in

April

Cheapest in

February

Average price

$246
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. 11% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This CheapTicketsDeal deal was found by Cheapflights users on 2/20. 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.
Sat 4/126:30 amYYZ - MDW
1 stop13h 03mWestJet
Sun 4/2010:20 amMDW - YYZ
1 stop24h 14mWestJet
Deal found 2/20$244
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 4/1812:15 pmYYZ - MDW
1 stop7h 05mDelta
Tue 4/223:02 pmMDW - YYZ
1 stop6h 53mDelta
Deal found 2/20$246
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 3/17:10 amYYZ - MDW
1 stop13h 19mMultiple Airlines
Tue 3/48:30 amMDW - YYZ
1 stop10h 00mMultiple Airlines
Deal found 2/20$325

Find flights from Pearson Intl to Midway within your budget

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 February 20, 2025.

Fly from

Pearson Intl

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/12

6:30 am-6:33 pm

1 stop13h 03m

Chicago Midway

Mon 4/21

1:16 pm-11:34 am

1 stop21h 18m

$244

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 3/20

10:20 am-12:36 pm

1 stop3h 16m

Chicago Midway

Mon 3/24

2:55 pm-10:38 pm

1 stop6h 43m

$247

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 3/20

8:00 pm-5:31 am

1 stop10h 31m

Chicago Midway

Mon 3/24

8:44 pm-9:11 pm

2 stops23h 27m

$328

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 5/4

7:45 am-10:40 pm

1 stop15h 55m

$136

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 3/20

10:20 am-12:36 pm

1 stop3h 16m

$154

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 5/28

12:31 pm-6:04 pm

1 stop6h 33m

$163

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 4/30

12:15 pm-6:20 pm

1 stop7h 05m

$170

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

  • 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.

Travel insights for flights from Pearson Intl to Midway

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

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 February 20, 2025.
See what other customers who have flown with Delta, KLM 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
8,220 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

8.0

Boarding

8.2

Overall

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
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

8.0

Boarding

8.2

Overall

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

KLM
7.8
Good
1,333 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

8.0

Boarding

8.2

Overall

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
2,801 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

8.0

Boarding

8.2

Overall

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?

    WestJet, at $244, 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 Delta. WestJet is 30% 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 Pearson Intl Airport to Chicago Midway Airport one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $154. However, be on the lookout for offers from WestJet and KLM, as they are both options that can get you from Toronto Pearson Intl Airport to Chicago Midway Airport for a low price.

  • 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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