Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 181
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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
6 Dec — 13 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 6 November 2025.
Tue 2/127:30 a.m.YYZ - ORD
1 stop7h 29mAmerican Airlines
Sat 6/128:00 a.m.ORD - YYZ
1 stop7h 35mAmerican Airlines
Deal found 4/11C$ 260
Thu 11/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 14/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 3/11C$ 265
Sun 23/116:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Mon 1/125:00 a.m.ORD - YYZ
1 stop5h 03mAmerican Airlines
Deal found 5/11C$ 268
Fri 5/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 7/125:00 a.m.ORD - YYZ
1 stop5h 02mAmerican Airlines
Deal found 4/11C$ 271
Thu 20/116:20 a.m.YYZ - ORD
1 stop5h 58mAir Canada
Mon 24/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 6/11C$ 272
Thu 11/124:50 p.m.YYZ - ORD
Nonstop1h 58mAir Canada
Mon 15/122:00 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 4/11C$ 274
Thu 20/117:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Wed 26/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 5/11C$ 275
Thu 27/112:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Thu 27/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 6/11C$ 282
Sat 6/129:00 a.m.YYZ - ORD
Nonstop2h 02mUnited Airlines
Sun 7/127:10 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 5/11C$ 284
Wed 26/113:30 p.m.YYZ - ORD
Nonstop2h 22mMultiple Airlines
Sun 30/118:00 a.m.ORD - YYZ
Nonstop1h 40mMultiple Airlines
Deal found 4/11C$ 285
Tue 2/126:30 p.m.YYZ - ORD
Nonstop2h 00mAir Canada
Tue 9/123:55 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 3/11C$ 286
Thu 4/1212:13 p.m.YYZ - MDW
1 stop6h 47mDelta
Thu 11/129:34 a.m.MDW - YYZ
1 stop6h 41mDelta
Deal found 5/11C$ 295
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 6 November 2025.
Mon 5/16:40 p.m.YYZ - ORD
1 stop5h 55mUnited Airlines
Wed 14/11:13 p.m.ORD - YYZ
Nonstop1h 49mUnited Airlines
Deal found 4/11C$ 272
Sun 11/16:00 a.m.YYZ - ORD
1 stop4h 40mDelta
Thu 15/111:05 a.m.ORD - YYZ
1 stop4h 07mDelta
Deal found 4/11C$ 284
Fri 21/115:30 p.m.YYZ - ORD
Nonstop2h 09mMultiple Airlines
Mon 24/118:15 p.m.ORD - YYZ
Nonstop1h 39mMultiple Airlines
Deal found 4/11C$ 285
Mon 5/17:45 a.m.YYZ - MDW
1 stop6h 03mDelta
Fri 9/16:30 p.m.MDW - YYZ
1 stop3h 11mDelta
Deal found 4/11C$ 284
Fri 28/1111:00 a.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Sun 30/119:20 p.m.ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 4/11C$ 285
Fri 21/119:00 p.m.YYZ - ORD
Nonstop2h 05mMultiple Airlines
Sat 29/118:00 a.m.ORD - YYZ
Nonstop1h 40mMultiple Airlines
Deal found 5/11C$ 285
Sun 11/16:00 a.m.YYZ - MDW
1 stop3h 54mDelta
Mon 12/16:14 p.m.MDW - YYZ
1 stop3h 27mDelta
Deal found 4/11C$ 284
Tue 30/129:00 a.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Thu 1/19:20 p.m.ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 5/11C$ 285
Thu 25/125:30 p.m.YYZ - ORD
Nonstop2h 20mMultiple Airlines
Tue 6/18:30 p.m.ORD - YYZ
Nonstop1h 39mMultiple Airlines
Deal found 5/11C$ 289
Sun 11/16:00 a.m.YYZ - MDW
1 stop3h 54mDelta
Thu 15/19:50 a.m.MDW - YYZ
1 stop5h 09mDelta
Deal found 4/11C$ 284
Tue 23/129:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Tue 6/16:28 p.m.ORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 3/11C$ 291
Mon 5/17:45 a.m.YYZ - MDW
1 stop6h 03mDelta
Tue 13/16:14 p.m.MDW - YYZ
1 stop3h 27mDelta
Deal found 4/11C$ 284
Wed 7/111:00 a.m.YYZ - ORD
Nonstop2h 08mUnited Airlines
Fri 9/16:17 p.m.ORD - YYZ
1 stop4h 29mUnited Airlines
Deal found 4/11C$ 291
Tue 6/19:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Thu 15/16:05 a.m.ORD - YYZ
1 stop4h 43mUnited Airlines
Deal found 4/11C$ 291
Thu 11/126:05 a.m.YYZ - MDW
1 stop3h 49mDelta
Sun 14/126:40 p.m.MDW - YYZ
1 stop3h 31mDelta
Deal found 5/11C$ 295
Fri 9/19:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Tue 13/11:00 p.m.ORD - YYZ
1 stop4h 57mUnited Airlines
Deal found 4/11C$ 291
Thu 4/1212:13 p.m.YYZ - MDW
1 stop6h 47mDelta
Thu 11/129:34 a.m.MDW - YYZ
1 stop6h 41mDelta
Deal found 5/11C$ 295
Tue 23/129:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Wed 7/17:10 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 3/11C$ 291
Tue 24/39:45 a.m.YYZ - MDW
1 stop3h 50mDelta
Wed 25/31:00 p.m.MDW - YYZ
1 stop3h 24mDelta
Deal found 5/11C$ 295
Thu 15/110:05 a.m.YYZ - MDW
1 stop3h 43mDelta
Sun 18/19:34 a.m.MDW - YYZ
1 stop8h 34mDelta
Deal found 5/11C$ 295
Sat 10/16:00 a.m.YYZ - MDW
1 stop3h 54mDelta
Wed 14/19:50 a.m.MDW - YYZ
1 stop5h 09mDelta
Deal found 4/11C$ 296
Thu 8/112:10 p.m.YYZ - MDW
1 stop6h 24mDelta
Fri 9/16:30 p.m.MDW - YYZ
1 stop3h 11mDelta
Deal found 4/11C$ 296
Wed 3/126:05 a.m.YYZ - MDW
1 stop3h 49mDelta
Wed 10/129:34 a.m.MDW - YYZ
1 stop4h 14mDelta
Deal found 5/11C$ 296
Fri 5/1212:13 p.m.YYZ - MDW
1 stop6h 47mDelta
Mon 8/126:40 p.m.MDW - YYZ
1 stop3h 31mDelta
Deal found 4/11C$ 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 6 November 2025.
Sat 17/112:05 p.m.YYZ - ORD
Nonstop1h 56mAir Canada
Mon 16/28:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 4/11C$ 260
Thu 11/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 14/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 3/11C$ 265
Thu 20/116:30 p.m.YYZ - ORD
Nonstop2h 00mAir Canada
Mon 24/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 6/11C$ 272
Thu 11/124:50 p.m.YYZ - ORD
Nonstop1h 58mAir Canada
Mon 15/122:00 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 4/11C$ 274
Thu 20/116:30 p.m.YYZ - ORD
Nonstop2h 00mAir Canada
Wed 26/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 5/11C$ 276
Thu 27/112:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Thu 27/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 6/11C$ 282
Sat 6/129:00 a.m.YYZ - ORD
Nonstop2h 02mUnited Airlines
Sun 7/127:10 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 5/11C$ 284
Tue 18/119:00 p.m.YYZ - ORD
Nonstop2h 05mMultiple Airlines
Tue 25/112:00 p.m.ORD - YYZ
Nonstop1h 39mMultiple Airlines
Deal found 4/11C$ 285
Thu 20/116:30 p.m.YYZ - ORD
Nonstop2h 00mAir Canada
Thu 27/112:00 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 4/11C$ 286
Wed 10/122:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Sat 30/58:25 p.m.ORD - YYZ
Nonstop1h 45mAir Canada
Deal found 5/11C$ 289
Wed 24/129:00 p.m.YYZ - ORD
Nonstop2h 05mMultiple Airlines
Mon 5/18:30 p.m.ORD - YYZ
Nonstop1h 39mMultiple Airlines
Deal found 5/11C$ 291
Last-minute flights from Pearson Intl to Chicago
Discover last-minute flight deals from Pearson Intl to Chicago. Data last updated 6 November 2025 and is based on user searches.
Sun 16/114:00 p.m.YYZ - ORD
1 stop19h 42mMultiple Airlines
Sat 29/116:45 a.m.ORD - YYZ
1 stop3h 39mMultiple Airlines
Deal found 6/11C$ 442
Sun 16/114:00 p.m.YYZ - ORD
1 stop19h 42mMultiple Airlines
Mon 24/113:53 p.m.ORD - YYZ
1 stop15h 02mMultiple Airlines
Deal found 4/11C$ 451
Fri 21/116:05 a.m.YYZ - MDW
1 stop3h 49mDelta
Sat 22/116:48 p.m.MDW - YYZ
1 stop3h 17mDelta
Deal found 5/11C$ 330
Fri 21/116:05 a.m.YYZ - MDW
1 stop3h 49mDelta
Sun 23/116:48 p.m.MDW - YYZ
1 stop3h 17mDelta
Deal found 6/11C$ 381
Sun 23/116:05 a.m.YYZ - MDW
1 stop3h 49mDelta
Sat 29/119:34 a.m.MDW - YYZ
1 stop4h 14mDelta
Deal found 4/11C$ 313
Thu 4/1212:13 p.m.YYZ - MDW
1 stop6h 47mDelta
Thu 11/129:34 a.m.MDW - YYZ
1 stop6h 41mDelta
Deal found 5/11C$ 295
Fri 5/126:05 a.m.YYZ - MDW
1 stop3h 49mDelta
Thu 11/129:34 a.m.MDW - YYZ
1 stop6h 41mDelta
Deal found 4/11C$ 296
Fri 5/1212:50 p.m.YYZ - MDW
1 stop10h 49mMultiple Airlines
Sun 7/126:37 p.m.MDW - YYZ
1 stop24h 23mMultiple Airlines
Deal found 6/11C$ 340
Fri 5/1210:55 a.m.YYZ - MDW
1 stop12h 44mMultiple Airlines
Fri 12/126:15 a.m.MDW - YYZ
2 stops31h 25mMultiple Airlines
Deal found 5/11C$ 344
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$ 363
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$ 323
Sat 27/126:00 a.m.YYZ - MDW
1 stop6h 06mDelta
Mon 5/11:28 p.m.MDW - YYZ
1 stop8h 13mDelta
Deal found 5/11C$ 365
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 6 November 2025.
Tue 2/1210:20 a.m.YYZ - ORD
1 stop10h 00mDelta
Deal found 5/11C$ 181
Fri 5/124:30 p.m.YYZ - ORD
1 stop8h 09mAmerican Airlines
Deal found 5/11C$ 182
Thu 20/116:20 a.m.YYZ - ORD
1 stop5h 58mAir Canada
Deal found 6/11C$ 183
Tue 18/116:20 a.m.YYZ - ORD
1 stop5h 58mAir Canada
Deal found 4/11C$ 186
Fri 28/116:05 a.m.YYZ - ORD
1 stop7h 39mDelta
Deal found 5/11C$ 188
Wed 26/116:05 a.m.YYZ - MDW
1 stop3h 49mDelta
Deal found 5/11C$ 188
Fri 12/127:15 a.m.YYZ - MDW
1 stop16h 24mMultiple Airlines
Deal found 6/11C$ 189
Tue 2/1210:10 a.m.YYZ - ORD
2 stops11h 00mAir Canada
Deal found 6/11C$ 192
Sun 23/118:15 a.m.YYZ - ORD
2 stops7h 40mAir Canada
Deal found 3/11C$ 193
Sun 7/129:00 a.m.YYZ - ORD
Nonstop2h 02mUnited Airlines
Deal found 4/11C$ 196
Fri 28/119:00 a.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Deal found 5/11C$ 198
Fri 26/127:40 p.m.YYZ - ORD
1 stop5h 04mUnited Airlines
Deal found 5/11C$ 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 6 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 6 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
Mon 5/1
6:40 p.m.-11:35 p.m.
1 stop5h 55m
Chicago O'Hare Intl
Wed 14/1
1:13 p.m.-4:02 p.m.
Nonstop1h 49m
C$ 272
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 11/1
6:00 a.m.-9:40 a.m.
1 stop4h 40m
Chicago O'Hare Intl
Thu 15/1
11:05 a.m.-4:12 p.m.
1 stop4h 07m
C$ 284
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$ 284
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$ 284
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$ 284
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$ 284
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 21/11
5:30 p.m.-6:39 p.m.
Nonstop2h 09m
Chicago O'Hare Intl
Mon 24/11
8:15 p.m.-10:54 p.m.
Nonstop1h 39m
C$ 285
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 28/11
11:00 a.m.-12:05 p.m.
Nonstop2h 05m
Chicago O'Hare Intl
Sun 30/11
9:20 p.m.-11:59 p.m.
Nonstop1h 39m
C$ 285
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 21/11
9:00 p.m.-10:05 p.m.
Nonstop2h 05m
Chicago O'Hare Intl
Sat 29/11
8:00 a.m.-10:40 a.m.
Nonstop1h 40m
C$ 285
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 30/12
9:00 a.m.-10:05 a.m.
Nonstop2h 05m
Chicago O'Hare Intl
Thu 1/1
9:20 p.m.-11:59 p.m.
Nonstop1h 39m
C$ 285
Flights are sorted by cheapest round-trip flights first.
Deals found on 5/11
Showing 1-10 of 46 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 31 October 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$ 182). Flying from Toronto Pearson Intl Airport to Chicago in April is currently the most expensive (average of C$ 299). 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 6 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 6 November 2025.
The most flights from YYZ to CHI are scheduled on a Monday (58 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (39 on average).
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 6 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 4h 40m. The time it takes to get you to your destination can typically vary by up to 1h 15m. 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$ 227, 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$ 266 and C$ 266, respectively. Users have found that Porter Airlines is 41% cheaper than the other options available to this destination.
What are the cheapest airlines to fly from Toronto Pearson Intl Airport to Chicago one-way?
One-way options have recently been found by users for as low as C$ 181 on Delta. Other airlines that offer cheap prices include American Airlines from C$ 182 and Air Canada from C$ 183 one-way.
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 (92%), ANA( 88%).
What are the cheapest flights from Toronto Pearson Intl Airport to Chicago?
On average you can expect to pay C$ 2,105 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 222 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 216.
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$ 182). Flying from Toronto Pearson Intl Airport to Chicago in April is currently the most expensive (average of C$ 299). 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 6 November 2025.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 6 November 2025.
Browse through other flights departing from Pearson Intl. Flights are based on user searches made on Cheapflights and were last updated on 6 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 6 November 2025.
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