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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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
12 dic. — 19 dic.1
1 adult
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

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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 12 noviembre 2025.

vie. 5/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
dom. 14/125:00 a.m.ORD - YYZ
1 stop5h 02mAmerican Airlines
Deal found 12/11C$ 271
jue. 27/116:00 a.m.YYZ - ORD
1 stop7h 56mAmerican Airlines
mar. 2/129:45 a.m.ORD - YYZ
Nonstop1h 47mAmerican Airlines
Deal found 9/11C$ 272
sáb. 6/124:50 p.m.YYZ - ORD
Nonstop1h 58mAir Canada
dom. 7/128:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 11/11C$ 275
mar. 9/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
mié. 10/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 10/11C$ 278
vie. 12/124:30 p.m.YYZ - ORD
1 stop8h 09mAmerican Airlines
dom. 11/18:07 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 10/11C$ 279
mié. 26/116:50 a.m.YYZ - ORD
Nonstop2h 06mMultiple Airlines
mié. 26/118:15 p.m.ORD - YYZ
Nonstop1h 39mMultiple Airlines
Deal found 10/11C$ 280
sáb. 6/126:05 a.m.YYZ - MDW
1 stop3h 44mKLM
lun. 8/126:40 p.m.MDW - YYZ
1 stop3h 31mKLM
Deal found 11/11C$ 280
mié. 26/119:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
dom. 30/111:19 p.m.ORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 11/11C$ 282
vie. 5/127:09 p.m.YYZ - ORD
1 stop5h 30mAmerican Airlines
dom. 7/126:05 a.m.ORD - YYZ
1 stop4h 51mAmerican Airlines
Deal found 12/11C$ 285
lun. 24/1110:00 a.m.YYZ - ORD
1 stop5h 55mAir Canada
jue. 27/113:55 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 10/11C$ 287
mié. 10/1211:00 a.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
vie. 9/17:10 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 10/11C$ 289
vie. 5/123:38 p.m.YYZ - MDW
1 stop3h 22mDelta
dom. 7/126:40 p.m.MDW - YYZ
1 stop3h 31mDelta
Deal found 12/11C$ 294

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 12 noviembre 2025.

Round-trip from

C$ 264

One-way from

C$ 181

Popular in

December

Cheapest in

September

Average price

C$ 442

Good round-trip deal

C$ 564 or less

Good one-way deal

C$ 351 or less
American Airlines
  • American Airlines
  • 7/1-14/1
  • 1 total stop
  • 6h 43m total
  • Toronto to Chicago
Search Deals
American Airlines
  • American Airlines
  • 11/1
  • 1 total stop
  • 6h 19m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Toronto Pearson Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Toronto Pearson Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
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 12 noviembre 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

vie. 6/2

9:00 a.m.-10:06 a.m.

Nonstop2h 06m

Chicago O'Hare Intl

mar. 10/2

6:17 p.m.-11:46 p.m.

1 stop4h 29m

C$ 289

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

vie. 26/12

6:50 a.m.-8:03 a.m.

Nonstop2h 13m

Chicago O'Hare Intl

mar. 6/1

1:13 p.m.-4:02 p.m.

Nonstop1h 49m

C$ 290

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

mar. 7/4

5:00 p.m.-9:46 p.m.

1 stop5h 46m

Chicago O'Hare Intl

sáb. 11/4

7:00 a.m.-3:20 p.m.

1 stop7h 20m

C$ 294

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

vie. 3/4

12:15 p.m.-6:46 p.m.

1 stop7h 31m

Chicago O'Hare Intl

mié. 15/4

10:35 a.m.-5:53 p.m.

1 stop6h 18m

C$ 294

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

vie. 3/4

12:15 p.m.-6:46 p.m.

1 stop7h 31m

Chicago O'Hare Intl

mar. 14/4

7:00 a.m.-3:18 p.m.

1 stop7h 18m

C$ 294

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

sáb. 4/4

6:00 a.m.-12:35 p.m.

1 stop7h 35m

Chicago Midway

mié. 15/4

9:30 a.m.-5:23 p.m.

1 stop6h 53m

C$ 294

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

vie. 5/12

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

1 stop3h 22m

Chicago Midway

dom. 7/12

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

1 stop3h 31m

C$ 294

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

vie. 3/4

6:00 a.m.-12:35 p.m.

1 stop7h 35m

Chicago Midway

sáb. 11/4

9:30 a.m.-5:24 p.m.

1 stop6h 54m

C$ 294

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

dom. 5/4

9:45 a.m.-12:35 p.m.

1 stop3h 50m

Chicago Midway

mié. 15/4

9:30 a.m.-5:23 p.m.

1 stop6h 53m

C$ 294

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

sáb. 4/4

3:59 p.m.-6:34 p.m.

1 stop3h 35m

Chicago Midway

mar. 14/4

9:30 a.m.-5:23 p.m.

1 stop6h 53m

C$ 294

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 43 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 7 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 12 noviembre 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 12 noviembre 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 (41 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 12 noviembre 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.
Porter Airlines
8.0
Very good
389 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

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
389 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

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.
United Airlines
7.4
Good
9,015 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

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.
American Airlines
7.2
Good
11,050 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

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
3,159 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

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.
Air Canada
7.1
Good
10,443 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

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 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 06m. The time it takes to get you to your destination can typically vary by up to 3h 40m. 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 (92%), ANA( 88%).

  • 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 flights from Pearson Intl to Chicago that include hotel bookings?

    Yes. In addition to deals on Pearson Intl to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pearson Intl to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pearson Intl to Chicago.

  • 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.

See more FAQs

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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 12 noviembre 2025.
Air Canada flights from Toronto Pearson Intl to Chicago
United Airlines flights from Toronto Pearson Intl to Chicago

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 12 noviembre 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 226AverageC$ 317FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
American AirlinesCheapestC$ 264AverageC$ 454FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 265AverageC$ 401FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 283AverageC$ 425FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 374AverageC$ 600FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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

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

Certainly. Search results for flights to Chicago from Pearson Intl shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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