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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 193

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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
25 Feb — 4 Mar1
1 adult

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 20 February 2025.

Round-trip from

C$ 347

One-way from

C$ 193

Popular in

April

Cheapest in

February

Average price

C$ 349
WestJet
  • WestJet
  • 12/4-20/4
  • 2 total stops
  • 37h 17m total
  • Toronto to Chicago
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4/5
  • 4/5
  • 1 total stop
  • 15h 55m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 94 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 20 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 20 February 2025.

Sat 12/46:30 a.m.YYZ - MDW
1 stop13h 03mWestJet
Mon 21/41:16 p.m.MDW - YYZ
1 stop21h 18mWestJet
Deal found 20/2C$ 347
Thu 20/310:20 a.m.YYZ - MDW
1 stop3h 16mDelta
Mon 24/32:55 p.m.MDW - YYZ
1 stop6h 43mDelta
Deal found 19/2C$ 351
Sat 1/37:10 a.m.YYZ - MDW
1 stop13h 19mMultiple Airlines
Tue 4/38:30 a.m.MDW - YYZ
1 stop10h 00mMultiple Airlines
Deal found 18/2C$ 443

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 629,999 searches. Data last updated 20 February 2025.

Fly from

Pearson Intl

Fly to

Midway

Route

Depart

Return

Price

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 12/4

6:30 a.m.-6:33 p.m.

1 stop13h 03m

Chicago Midway

Sun 20/4

10:20 a.m.-11:34 a.m.

1 stop24h 14m

C$ 347

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 20/3

10:20 a.m.-12:36 p.m.

1 stop3h 16m

Chicago Midway

Mon 24/3

2:55 p.m.-10:38 p.m.

1 stop6h 43m

C$ 351

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 1/3

7:10 a.m.-7:29 p.m.

1 stop13h 19m

Chicago Midway

Tue 4/3

8:30 a.m.-7:30 p.m.

1 stop10h 00m

C$ 443

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 4/5

7:45 a.m.-10:40 p.m.

1 stop15h 55m

C$ 193

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 20/3

10:20 a.m.-12:36 p.m.

1 stop3h 16m

C$ 219

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 22/3

2:45 p.m.-6:33 p.m.

1 stop4h 48m

C$ 237

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 30/4

12:15 p.m.-6:20 p.m.

1 stop7h 05m

C$ 241

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/2

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, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of C$ 243). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 YYZ to MDW?

Find hourly flight availability from Pearson Intl 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 20 February 2025.

It’s optimal to fly from Toronto Pearson Intl Airport to Chicago Midway Airport in the evening. By choosing this option you can save up to 35% on the cost of your flight, compared to a flight in the afternoon.

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 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 43.0 mm.

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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 20 February 2025.
See what other customers who have flown with Delta, KLM and WestJet from Toronto to Chicago have to say. 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
8,219 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

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
8,219 reviews
Delta
8.0
Very good
8,219 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

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
8,219 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

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
8,219 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

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?

    Our cheapest airline available from Toronto Pearson Intl Airport to Chicago Midway Airport is WestJet. Our recent data shows that you can find tickets from as low as C$ 347 on this airline. An additional option worth looking into is Delta, starting at C$ 349. These flights start at 30% lower than the current average price 3 months from now.

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

    The cheapest airlines for a one-way flight from Toronto Pearson Intl Airport to Chicago Midway Airport are Delta (C$ 219), WestJet (C$ 237), and KLM (C$ 241).

  • 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, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of C$ 243). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 Pearson Intl to Midway

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

Top 2 airlines flying from Pearson Intl to Midway

Discover the top 2 airlines that operate flights from Pearson Intl 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 629,999 searches. Data last updated 20 February 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 267AverageC$ 369FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 450AverageC$ 650FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Pearson Intl to Midway?

Cheapflights makes it easy to find Pearson Intl to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Pearson Intl to Midway?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Pearson Intl to Midway.

Can Cheapflights find flights from Pearson Intl to Midway with no change fees?

Yes, we can. To see specific flights from Pearson Intl to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Pearson Intl to Midway become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Midway from Pearson Intl today and book when prices fit your budget.

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