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Cheap flights from Toronto Pearson Intl Airport to Chicago Midway Airport from C$ 187

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 26/11. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — MDW
5 Dec — 12 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Pearson Intl to Midway

Enter your travel dates to find the best prices.

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 5 November 2025.

Fri 5/1212:13 p.m.YYZ - MDW
1 stop6h 47mDelta
Tue 9/129:34 a.m.MDW - YYZ
1 stop4h 14mDelta
Deal found 4/11C$ 296
Thu 11/126:05 a.m.YYZ - MDW
1 stop7h 29mKLM
Sun 14/129:34 a.m.MDW - YYZ
1 stop6h 41mKLM
Deal found 2/11C$ 300
Thu 11/126:05 a.m.YYZ - MDW
1 stop7h 29mDelta
Mon 15/126:40 p.m.MDW - YYZ
1 stop3h 31mDelta
Deal found 4/11C$ 313
Sun 14/126:05 a.m.YYZ - MDW
1 stop7h 29mDelta
Mon 22/126:08 p.m.MDW - YYZ
1 stop3h 42mDelta
Deal found 5/11C$ 322
Fri 21/116:05 a.m.YYZ - MDW
1 stop3h 49mDelta
Sat 22/116:48 p.m.MDW - YYZ
1 stop3h 17mDelta
Deal found 4/11C$ 329
Mon 8/126:05 a.m.YYZ - MDW
1 stop3h 49mDelta
Thu 11/129:34 a.m.MDW - YYZ
1 stop6h 41mDelta
Deal found 5/11C$ 362
Thu 20/116:05 a.m.YYZ - MDW
1 stop3h 49mDelta
Wed 26/116:48 p.m.MDW - YYZ
1 stop3h 17mDelta
Deal found 5/11C$ 365
Thu 11/123:38 p.m.YYZ - MDW
1 stop3h 22mDelta
Sun 14/126:40 p.m.MDW - YYZ
1 stop3h 31mDelta
Deal found 3/11C$ 366
Sat 27/126:00 a.m.YYZ - MDW
1 stop6h 06mDelta
Wed 7/16:14 p.m.MDW - YYZ
1 stop3h 27mDelta
Deal found 3/11C$ 370
Sat 27/126:00 a.m.YYZ - MDW
1 stop6h 06mDelta
Tue 6/11:28 p.m.MDW - YYZ
1 stop4h 45mDelta
Deal found 3/11C$ 376
Fri 21/116:05 a.m.YYZ - MDW
1 stop3h 49mDelta
Sun 23/116:48 p.m.MDW - YYZ
1 stop3h 17mDelta
Deal found 5/11C$ 382

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 5 November 2025.

Round-trip from

C$ 283

One-way from

C$ 187

Popular in

September

Cheapest in

February

Average price

C$ 334
Delta
  • Delta
  • 5/1-12/1
  • 2 total stops
  • 9h 30m total
  • Toronto to Chicago
Search Deals
Delta
  • Delta
  • 26/11
  • 1 total stop
  • 3h 49m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 31% potential increase in price (C$ 299 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 45 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 629,999 searches. Data last updated 5 November 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

Mon 5/1

7:45 a.m.-12:48 p.m.

1 stop6h 03m

Chicago Midway

Fri 9/1

6:30 p.m.-10:41 p.m.

1 stop3h 11m

C$ 283

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 11/1

6:00 a.m.-8:54 a.m.

1 stop3h 54m

Chicago Midway

Mon 12/1

6:14 p.m.-10:41 p.m.

1 stop3h 27m

C$ 283

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 11/1

6:00 a.m.-8:54 a.m.

1 stop3h 54m

Chicago Midway

Thu 15/1

9:50 a.m.-3:59 p.m.

1 stop5h 09m

C$ 283

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 5/1

7:45 a.m.-12:48 p.m.

1 stop6h 03m

Chicago Midway

Mon 12/1

6:14 p.m.-10:41 p.m.

1 stop3h 27m

C$ 283

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 11/1

6:00 a.m.-8:54 a.m.

1 stop3h 54m

Chicago Midway

Tue 13/1

6:14 p.m.-10:41 p.m.

1 stop3h 27m

C$ 283

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 5/1

7:45 a.m.-12:48 p.m.

1 stop6h 03m

Chicago Midway

Tue 13/1

6:14 p.m.-10:41 p.m.

1 stop3h 27m

C$ 283

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 10/1

6:00 a.m.-8:54 a.m.

1 stop3h 54m

Chicago Midway

Wed 14/1

9:50 a.m.-3:59 p.m.

1 stop5h 09m

C$ 296

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 8/1

6:00 a.m.-8:54 a.m.

1 stop3h 54m

Chicago Midway

Tue 13/1

9:50 a.m.-3:59 p.m.

1 stop5h 09m

C$ 296

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 3/12

3:38 p.m.-6:00 p.m.

1 stop3h 22m

Chicago Midway

Wed 10/12

9:34 a.m.-2:48 p.m.

1 stop4h 14m

C$ 296

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 5/12

12:13 p.m.-6:00 p.m.

1 stop6h 47m

Chicago Midway

Mon 8/12

6:40 p.m.-11:11 p.m.

1 stop3h 31m

C$ 296

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 22 results
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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, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of C$ 182). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in October is currently the most expensive (average of C$ 491). 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 5 November 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 34% on the cost of your flight, compared to a flight in the afternoon.

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 5 November 2025.
Read reviews from past customers who have flown Porter Airlines and WestJet from Toronto Pearson Intl Airport to Chicago Midway Airport. 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.
Porter Airlines
8.0
Very good
387 reviews
Check prices

Food

7.6

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
387 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Food

7.6

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
WestJet
7.2
Good
3,154 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Food

7.6

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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.

  • How long is the flight from Toronto Pearson Intl Airport to Chicago Midway Airport?

    Airlines like Delta fly from Toronto Pearson Intl Airport to Chicago Midway Airport in about 6h 03m. The time it takes to get you to your destination can typically vary by up to . The distance from Toronto Pearson Intl Airport to Chicago Midway Airport is about 695 km.

  • 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 Porter Airlines. Our recent data shows that you can find tickets from as low as C$ 232 on this airline. An additional option worth looking into is WestJet, starting at C$ 559. These flights start at 48% lower than the current average price 3 months from now.

  • 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, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport (average of C$ 182). Flying from Toronto Pearson Intl Airport to Chicago Midway Airport in October is currently the most expensive (average of C$ 491). 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
Toronto Island to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Region of Waterloo Intl 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 5 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 232AverageC$ 355FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 559AverageC$ 690FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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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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