Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 170
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 13/12. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
19 Dec — 26 Dec1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago are usually found in September or August, booked 84 days in advance, depart on a Friday or Saturday and return on a Thursday
Find flight deals from Pearson Intl to Chicago
Enter your travel dates to find the best prices.
Cheapest flights from Pearson Intl to Chicago
Explore the most affordable flight options available from Pearson Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 19 November 2025.
Tue 9/121:47 p.m.YYZ - ORD
1 stop5h 36mAmerican Airlines
Fri 12/125:00 a.m.ORD - YYZ
1 stop5h 12mAmerican Airlines
Deal found 18/11C$ 257
Sat 13/127:30 a.m.YYZ - ORD
1 stop7h 34mAmerican Airlines
Mon 15/1211:31 a.m.ORD - YYZ
1 stop4h 04mAmerican Airlines
Deal found 16/11C$ 258
Fri 5/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Mon 8/126:04 a.m.ORD - YYZ
1 stop4h 52mAmerican Airlines
Deal found 17/11C$ 266
Mon 8/124:13 p.m.YYZ - ORD
1 stop7h 41mAmerican Airlines
Thu 11/129:39 a.m.ORD - YYZ
Nonstop1h 51mAmerican Airlines
Deal found 16/11C$ 278
Tue 9/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sat 13/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 18/11C$ 279
Thu 4/122:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Sun 7/128:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 18/11C$ 280
Sun 14/126:30 a.m.YYZ - ORD
1 stop6h 10mDelta
Tue 16/122:35 p.m.ORD - YYZ
1 stop4h 52mDelta
Deal found 19/11C$ 282
Sun 14/129:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Tue 16/124:50 p.m.ORD - YYZ
Nonstop1h 55mUnited Airlines
Deal found 19/11C$ 283
Mon 8/1210:58 a.m.YYZ - ORD
1 stop6h 53mAmerican Airlines
Fri 12/125:00 a.m.ORD - YYZ
1 stop5h 12mAmerican Airlines
Deal found 17/11C$ 285
Sun 7/126:00 a.m.YYZ - ORD
1 stop7h 54mAmerican Airlines
Wed 10/125:00 a.m.ORD - YYZ
1 stop5h 12mAmerican Airlines
Deal found 19/11C$ 287
Fri 26/126:50 a.m.YYZ - ORD
Nonstop2h 13mUnited Airlines
Wed 7/111:15 a.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 17/11C$ 289
Fri 26/126:50 a.m.YYZ - ORD
Nonstop2h 13mUnited Airlines
Tue 6/16:28 p.m.ORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 19/11C$ 290
Best flights from Pearson Intl to Chicago
Discover carefully curated flight deals from Pearson Intl to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 19 November 2025.
Sun 1/29:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Thu 5/27:10 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 17/11C$ 258
Thu 11/126:05 a.m.YYZ - MDW
1 stop7h 29mDelta
Tue 16/129:34 a.m.MDW - YYZ
1 stop4h 14mDelta
Deal found 18/11C$ 294
Thu 29/19:00 a.m.YYZ - ORD
Nonstop2h 06mUnited Airlines
Mon 16/26:28 p.m.ORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 17/11C$ 258
Thu 8/19:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Sun 11/19:15 p.m.ORD - YYZ
Nonstop1h 44mUnited Airlines
Deal found 19/11C$ 259
Sun 25/16:00 a.m.YYZ - MDW
1 stop7h 46mDelta
Thu 29/11:26 p.m.MDW - YYZ
1 stop4h 42mDelta
Deal found 18/11C$ 294
Sat 14/23:30 p.m.YYZ - ORD
Nonstop2h 09mUnited Airlines
Tue 17/26:00 a.m.ORD - YYZ
1 stop4h 48mUnited Airlines
Deal found 17/11C$ 264
Sat 14/26:15 a.m.YYZ - MDW
1 stop7h 33mDelta
Tue 17/29:34 a.m.MDW - YYZ
1 stop8h 34mDelta
Deal found 17/11C$ 294
Wed 7/16:00 a.m.YYZ - MDW
1 stop3h 52mDelta
Fri 9/11:28 p.m.MDW - YYZ
1 stop4h 45mDelta
Deal found 16/11C$ 294
Sun 14/129:00 a.m.YYZ - ORD
Nonstop2h 02mUnited Airlines
Wed 17/127:10 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 19/11C$ 283
Tue 24/39:45 a.m.YYZ - MDW
1 stop3h 50mDelta
Wed 25/31:00 p.m.MDW - YYZ
1 stop3h 24mDelta
Deal found 16/11C$ 294
Sun 7/129:00 a.m.YYZ - ORD
Nonstop2h 02mUnited Airlines
Sat 13/127:10 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 17/11C$ 283
Wed 11/26:00 a.m.YYZ - MDW
1 stop3h 52mDelta
Thu 12/21:28 p.m.MDW - YYZ
1 stop4h 40mDelta
Deal found 16/11C$ 294
Mon 15/123:30 p.m.YYZ - ORD
Nonstop2h 22mUnited Airlines
Wed 17/127:10 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 19/11C$ 283
Fri 13/210:05 a.m.YYZ - MDW
1 stop8h 32mDelta
Mon 16/29:34 a.m.MDW - YYZ
1 stop8h 34mDelta
Deal found 17/11C$ 294
Mon 15/129:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Tue 16/1211:15 a.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 19/11C$ 283
Sun 14/126:30 a.m.YYZ - MDW
1 stop7h 40mDelta
Wed 17/121:14 p.m.MDW - YYZ
1 stop3h 01mDelta
Deal found 17/11C$ 294
Tue 13/111:00 a.m.YYZ - ORD
Nonstop2h 08mUnited Airlines
Thu 15/16:17 p.m.ORD - YYZ
1 stop4h 29mUnited Airlines
Deal found 18/11C$ 289
Thu 1/16:00 a.m.YYZ - MDW
1 stop6h 06mDelta
Thu 8/11:28 p.m.MDW - YYZ
1 stop4h 45mDelta
Deal found 16/11C$ 294
Fri 26/129:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Fri 9/17:10 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 17/11C$ 289
Thu 8/16:00 a.m.YYZ - MDW
1 stop7h 48mDelta
Sun 11/11:49 p.m.MDW - YYZ
1 stop8h 24mDelta
Deal found 17/11C$ 294
Thu 5/26:00 a.m.YYZ - MDW
1 stop3h 52mDelta
Sat 7/21:26 p.m.MDW - YYZ
1 stop8h 16mDelta
Deal found 19/11C$ 296
Direct flights from Pearson Intl to Chicago
Explore direct flight options from Pearson Intl to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 19 November 2025.
Thu 19/38:55 a.m.YYZ - ORD
Nonstop2h 07mUnited Airlines
Sun 22/39:14 p.m.ORD - YYZ
Nonstop1h 38mUnited Airlines
Deal found 19/11C$ 258
Thu 8/15:30 p.m.YYZ - ORD
Nonstop2h 20mUnited Airlines
Sun 11/14:50 p.m.ORD - YYZ
Nonstop1h 55mUnited Airlines
Deal found 18/11C$ 259
Thu 8/19:00 p.m.YYZ - ORD
Nonstop2h 05mLufthansa
Sun 11/16:28 p.m.ORD - YYZ
Nonstop1h 53mLufthansa
Deal found 17/11C$ 268
Tue 9/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sat 13/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 18/11C$ 279
Thu 4/122:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Sun 7/128:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 18/11C$ 280
Sun 14/129:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Tue 16/124:50 p.m.ORD - YYZ
Nonstop1h 55mUnited Airlines
Deal found 19/11C$ 283
Fri 12/122:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Sat 13/128:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 18/11C$ 285
Fri 26/129:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Thu 8/11:13 p.m.ORD - YYZ
Nonstop1h 49mUnited Airlines
Deal found 17/11C$ 289
Fri 26/129:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Tue 6/111:15 a.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 18/11C$ 290
Sun 8/39:00 p.m.YYZ - ORD
Nonstop2h 04mAir Canada
Wed 11/38:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 17/11C$ 293
Wed 3/124:50 p.m.YYZ - ORD
Nonstop1h 58mAir Canada
Sat 6/128:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 17/11C$ 303
Thu 4/122:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Thu 25/128:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 18/11C$ 310
Last-minute flights from Pearson Intl to Chicago
Discover last-minute flight deals from Pearson Intl to Chicago. Data last updated 19 November 2025 and is based on user searches.
Thu 4/122:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Sun 7/128:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 18/11C$ 280
Fri 5/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Mon 8/126:04 a.m.ORD - YYZ
1 stop4h 52mAmerican Airlines
Deal found 17/11C$ 266
Sun 7/126:00 a.m.YYZ - ORD
1 stop7h 54mAmerican Airlines
Wed 10/125:00 a.m.ORD - YYZ
1 stop5h 12mAmerican Airlines
Deal found 19/11C$ 287
Mon 8/124:13 p.m.YYZ - ORD
1 stop7h 41mAmerican Airlines
Thu 11/129:39 a.m.ORD - YYZ
Nonstop1h 51mAmerican Airlines
Deal found 16/11C$ 278
Mon 8/1210:58 a.m.YYZ - ORD
1 stop6h 53mAmerican Airlines
Fri 12/125:00 a.m.ORD - YYZ
1 stop5h 12mAmerican Airlines
Deal found 17/11C$ 285
Tue 9/121:47 p.m.YYZ - ORD
1 stop5h 36mAmerican Airlines
Fri 12/125:00 a.m.ORD - YYZ
1 stop5h 12mAmerican Airlines
Deal found 18/11C$ 257
Tue 9/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sat 13/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 18/11C$ 279
Sat 13/125:16 p.m.YYZ - ORD
1 stop5h 03mAmerican Airlines
Tue 16/123:44 p.m.ORD - YYZ
1 stop5h 49mAmerican Airlines
Deal found 16/11C$ 258
Sun 14/126:30 a.m.YYZ - ORD
1 stop6h 10mDelta
Tue 16/122:35 p.m.ORD - YYZ
1 stop4h 52mDelta
Deal found 19/11C$ 282
Sun 14/129:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Tue 16/124:50 p.m.ORD - YYZ
Nonstop1h 55mUnited Airlines
Deal found 19/11C$ 283
Fri 26/126:50 a.m.YYZ - ORD
Nonstop2h 13mUnited Airlines
Wed 7/111:15 a.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 17/11C$ 289
Fri 26/129:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Tue 6/111:15 a.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 18/11C$ 290
One-way flights from Pearson Intl to Chicago
Search for one-way flight options from Pearson Intl to Chicago. Find affordable one-way fares based on user searches. Data last updated 19 November 2025.
Sat 13/127:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Deal found 18/11C$ 170
Wed 3/124:50 p.m.YYZ - ORD
Nonstop1h 58mAir Canada
Deal found 17/11C$ 174
Wed 3/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Deal found 18/11C$ 175
Sat 6/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Deal found 17/11C$ 178
Thu 15/17:50 a.m.YYZ - ORD
1 stop9h 32mDelta
Deal found 19/11C$ 179
Thu 1/16:05 a.m.YYZ - MDW
1 stop3h 44mDelta
Deal found 17/11C$ 179
Sat 13/127:30 a.m.YYZ - ORD
1 stop7h 34mAmerican Airlines
Deal found 17/11C$ 181
Tue 2/122:00 p.m.YYZ - ORD
1 stop7h 10mAir Canada
Deal found 17/11C$ 185
Thu 1/16:05 a.m.YYZ - ORD
1 stop3h 56mDelta
Deal found 17/11C$ 186
Thu 15/17:10 a.m.YYZ - ORD
2 stops8h 45mAir Canada
Deal found 19/11C$ 191
Sat 6/128:15 a.m.YYZ - ORD
2 stops7h 40mAir Canada
Deal found 17/11C$ 192
Mon 1/1212:08 p.m.YYZ - MDW
1 stop7h 00mDelta
Deal found 17/11C$ 199
Cheap flight deals from Pearson Intl to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Pearson Intl (YYZ) to Chicago (CHI). 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 19 November 2025.
Customize your flight search to find flights from Pearson Intl to Chicago 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 19 November 2025.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago that are best for you.
Fly from
Pearson Intl
Fly to
Chicago
Route
Depart
Return
Price
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 1/2
9:00 p.m.-10:05 p.m.
Nonstop2h 05m
Chicago O'Hare Intl
Thu 5/2
7:10 a.m.-9:58 a.m.
Nonstop1h 48m
C$ 258
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 29/1
9:00 a.m.-10:06 a.m.
Nonstop2h 06m
Chicago O'Hare Intl
Mon 16/2
6:28 p.m.-9:21 p.m.
Nonstop1h 53m
C$ 258
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 8/1
9:00 p.m.-10:05 p.m.
Nonstop2h 05m
Chicago O'Hare Intl
Sun 11/1
9:15 p.m.-11:59 p.m.
Nonstop1h 44m
C$ 259
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 14/2
3:30 p.m.-4:39 p.m.
Nonstop2h 09m
Chicago O'Hare Intl
Tue 17/2
6:00 a.m.-11:48 a.m.
1 stop4h 48m
C$ 264
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 14/12
9:00 a.m.-10:02 a.m.
Nonstop2h 02m
Chicago O'Hare Intl
Wed 17/12
7:10 a.m.-9:58 a.m.
Nonstop1h 48m
C$ 283
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 7/12
9:00 a.m.-10:02 a.m.
Nonstop2h 02m
Chicago O'Hare Intl
Sat 13/12
7:10 a.m.-9:58 a.m.
Nonstop1h 48m
C$ 283
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 15/12
3:30 p.m.-4:52 p.m.
Nonstop2h 22m
Chicago O'Hare Intl
Wed 17/12
7:10 a.m.-9:58 a.m.
Nonstop1h 48m
C$ 283
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 15/12
9:00 p.m.-10:05 p.m.
Nonstop2h 05m
Chicago O'Hare Intl
Tue 16/12
11:15 a.m.-2:01 p.m.
Nonstop1h 46m
C$ 283
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 13/1
11:00 a.m.-12:08 p.m.
Nonstop2h 08m
Chicago O'Hare Intl
Thu 15/1
6:17 p.m.-11:46 p.m.
1 stop4h 29m
C$ 289
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 26/12
9:00 p.m.-10:05 p.m.
Nonstop2h 05m
Chicago O'Hare Intl
Fri 9/1
7:10 a.m.-9:58 a.m.
Nonstop1h 48m
C$ 289
Flights are sorted by cheapest round-trip flights first.
Deals found on 19/11
Showing 1-10 of 39 results
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Best time to book a flight from Pearson Intl to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago 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
How far ahead should I book a flight from Toronto Pearson Intl Airport to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Pearson Intl to Chicago. Price data was last updated on 14 November 2025.
Booking 84 days in advance of your planned departure date is, on average, the best time to get cheap flights from Toronto Pearson Intl Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Toronto Pearson Intl Airport to Chicago?
Currently, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of C$ 181). Flying from Toronto Pearson Intl Airport to Chicago in April is currently the most expensive (average of C$ 297). 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 CHI?
Find hourly flight availability from Pearson Intl to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 19 November 2025.
It’s optimal to fly from Toronto Pearson Intl Airport to Chicago in the evening. By choosing this option you can save up to 38% on the cost of your flight, compared to a flight at noon.
What is the cheapest day to fly from Toronto Pearson Intl Airport to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Pearson Intl to Chicago. Price data was last updated on 16 December 2024.
Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago flight should consider departing on Thursday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Toronto Pearson Intl Airport to Chicago
Explore weekly flight availability from Pearson Intl to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 19 November 2025.
The most flights from YYZ to CHI are scheduled on a Monday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (51 on average).
How much does it cost to fly round-trip from Toronto Pearson Intl Airport to Chicago?
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated 19 November 2025.
Read reviews from past customers who have flown Porter Airlines,United Airlines, andAmerican Airlines
from Toronto Pearson Intl Airport to Chicago. 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.
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.
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.
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.
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.
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.
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 Chicago. 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?
Airlines like United Airlines and Delta fly from Toronto Pearson Intl Airport to Chicago in about 2h 05m. The time it takes to get you to your destination can typically vary by up to 5h 24m. The distance between Toronto Pearson Intl Airport and Chicago is about 702 km. This flight may include one or multiple stops.
What are the cheapest airlines flying from Toronto Pearson Intl Airport to Chicago round-trip?
Currently priced at C$ 226, Porter Airlines will fly you from Toronto Pearson Intl Airport to Chicago and back. In addition to Porter Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and Air Canada - these airlines can fly you to your destination from C$ 264 and C$ 265, respectively. Users have found that Porter Airlines is 40% cheaper than the other options available to this destination.
What are the most reliable airlines from Toronto Pearson Intl Airport to Chicago?
Before booking your flight to Chicago from Toronto Pearson Intl Airport, check out the most reliable airlines to get you to your destination on time: EVA Air (94%), Egyptair (87%), ANA( 86%).
What are the cheapest flights from Toronto Pearson Intl Airport to Chicago?
On average you can expect to pay C$ 2,092 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 220 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 215.
Can I find deals for business class flights from Pearson Intl to Chicago?
Yes. Cheapflights offers flight deals from Pearson Intl to Chicago 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?
Currently, August is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of C$ 181). Flying from Toronto Pearson Intl Airport to Chicago in April is currently the most expensive (average of C$ 297). 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.
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Fly from Pearson Intl to Chicago on these airlines
Choose from the following airlines for your flight from Pearson Intl to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 19 November 2025.
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Browse through other flights departing from Pearson Intl. Flights are based on user searches made on Cheapflights and were last updated on 19 November 2025.
Top 5 airlines flying from Pearson Intl to Chicago
Discover the top 5 airlines that operate flights from Pearson Intl to Chicago. 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 19 November 2025.
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