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$130+ Cheap flights from Toronto (YTO) to Chicago (CHI)

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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Toronto to Chicago are usually found in July or June, booked 77 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap flight deals from Toronto to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Toronto (YTO) 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$181
(SmartFares)

One-way from

$130
(American Airlines)

Popular in

October

Cheapest in

July

Average price

$296

Good round-trip deal

$333 or less

Good one-way deal

$189 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
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From Toronto (YTO) to Chicago (CHI)
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One-way flight from Toronto (YTO) to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Toronto (YTO) to Chicago (CHI).
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Price to beat on a one-way flight from Toronto (YTO) to Chicago (CHI).
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Find flight deals from Toronto to Chicago

Cheapest flights from Toronto to Chicago
Explore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This SmartFares deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:00 amYYZ - ORD
1 stop5h 18mAir Canada
Mon 11/178:15 pmORD - YYZ
Nonstop1h 39mAir Canada
Deal found 10/29$181
This Air Canada deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:00 amYYZ - ORD
1 stop5h 18mAir Canada
Thu 2/122:00 pmORD - YYZ
Nonstop1h 39mAir Canada
Deal found 10/29$183
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/310:58 amYYZ - ORD
1 stop9h 23mAmerican Airlines
Thu 2/127:19 amORD - YYZ
1 stop4h 43mAmerican Airlines
Deal found 10/29$184
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/239:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 12/1211:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$185
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/249:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 12/811:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$187
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/179:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 11/2212:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$188
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:00 amYYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 12/148:10 amORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 10/29$189
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/186:00 amYYZ - ORD
Nonstop2h 15mAmerican Airlines
Thu 11/207:35 amORD - YYZ
1 stop4h 27mAmerican Airlines
Deal found 10/29$190
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/149:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 11/174:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/29$190
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/64:44 pmYYZ - ORD
Nonstop2h 00mAmerican Airlines
Tue 12/96:22 amORD - YYZ
1 stop5h 38mAmerican Airlines
Deal found 10/28$193
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/119:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 12/1411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/29$193
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:00 amYYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 12/75:00 amORD - YYZ
1 stop5h 02mAmerican Airlines
Deal found 10/29$194

Cheapflights Fare Finder

 
Customize your flight search to find flights from Toronto 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 2,558,603 searches. Data last updated October 30, 2025.
Use the filters below to find and compare flights from Toronto to Chicago that are best for you.

Fly from

Toronto

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 1/16

2:15 pm-3:10 pm

Nonstop1h 55m

Chicago O'Hare Intl

Mon 1/19

3:35 pm-11:04 pm

1 stop6h 29m

$183

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 2/27

3:30 pm-4:39 pm

Nonstop2h 09m

Chicago O'Hare Intl

Sun 3/1

4:47 pm-7:45 pm

Nonstop1h 58m

$184

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 2/24

8:55 am-10:02 am

Nonstop2h 07m

Chicago O'Hare Intl

Sat 2/28

8:15 pm-10:54 pm

Nonstop1h 39m

$184

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/26

6:30 pm-7:30 pm

Nonstop2h 00m

Chicago O'Hare Intl

Sun 3/1

2:00 pm-4:39 pm

Nonstop1h 39m

$185

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 11/22

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Tue 11/25

11:00 am-1:42 pm

Nonstop1h 42m

$197

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 11/24

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Mon 12/1

11:00 am-1:42 pm

Nonstop1h 42m

$199

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/28

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Fri 12/5

4:15 pm-6:57 pm

Nonstop1h 42m

$201

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/4

6:24 pm-7:24 pm

Nonstop2h 00m

Chicago O'Hare Intl

Fri 12/5

9:39 am-12:30 pm

Nonstop1h 51m

$202

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/18

9:00 pm-10:05 pm

Nonstop2h 05m

Chicago O'Hare Intl

Tue 1/13

1:13 pm-4:02 pm

Nonstop1h 49m

$207

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/17

6:50 am-8:03 am

Nonstop2h 13m

Chicago O'Hare Intl

Wed 1/14

9:15 pm-11:59 pm

Nonstop1h 44m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 60 results
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Compare providers for flights from Toronto to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Toronto to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust Score*1 star
oojoPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Toronto-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Toronto-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Toronto-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Toronto-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Toronto to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Toronto 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 to Chicago

How far ahead should I book a flight from Toronto to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Toronto to Chicago. Price data was last updated on October 24, 2025.

To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 77 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Toronto to Chicago?

Currently, June is the cheapest month in which you can book a flight from Toronto to Chicago (average of $83). Flying from Toronto to Chicago in February is currently the most expensive (average of $190). 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 YTO to CHI?

Find hourly flight availability from Toronto 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 October 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Toronto to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 21% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from Toronto to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Toronto to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Tuesday at noon when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Toronto to Chicago?

The best insider tips for Toronto to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Toronto to Chicago trip
Airports
YYZ

Toronto Pearson offers fast security lines for US-bound flights, but arrive early to clear US customs before boarding.

Read more about YYZby Kaitlyn McInnis
ORD

At ORD, consider taking the “L” train to avoid traffic when heading to downtown Chicago.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Kaitlyn McInnis

Kaitlyn McInnis

Expert on YYZ

Kaitlyn McInnis

Kaitlyn McInnis

Kaitlyn is a guidebook author and travel writer splitting her time between Atlantic Canada and Istanbul, Türkiye. She has visited over fifty countries and all seven continents, so she is very familiar with many hotels, airports and airlines around the globe. But her favorite type of vacation is sunbathing by the sea with a good book in hand.

Read more

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 October 30, 2025.
Peruse reviews from past customers who have flown with Porter Airlines, Air Transat, and United Airlines from Toronto to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
384 reviews

Crew

8.6

Comfort

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews

Crew

8.6

Comfort

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Transat
7.8
Good
469 reviews
Porter Airlines
8.0
Very good
384 reviews

Crew

8.6

Comfort

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,998 reviews
Porter Airlines
8.0
Very good
384 reviews

Crew

8.6

Comfort

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
American Airlines
7.2
Good
11,030 reviews
Porter Airlines
8.0
Very good
384 reviews

Crew

8.6

Comfort

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,377 reviews
Porter Airlines
8.0
Very good
384 reviews

Crew

8.6

Comfort

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

Related info for your journey

Find useful and relevant information for your journey from Toronto 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 to Chicago?

    Air Canada, United Airlines, and Porter Airlines can get you from Toronto to Chicago in just under 1h 50m. Your travel time will be generally consistent. There are 442 mi between Toronto and Chicago. Generally, flights for this route are nonstop.

  • What are the cheapest airlines flying from Toronto to Chicago round-trip?

    Our cheapest airline available from Toronto to Chicago is Air Canada. Our recent data shows that you can find tickets from as low as $147 on this airline. Additional options worth looking into are Porter Airlines and United Airlines, starting at $158 and $165 round-trip. Air Canada is currently priced 42% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Toronto to Chicago one-way?

    For one-way options, check prices for Air Canada. According to our data, you can fly for as low as $132. Users have also found prices from $133 and $134 on Porter Airlines and Delta, respectively.

  • What are the most popular routes from Toronto to Chicago?

    The most popular flight routes from Toronto to Chicago are Toronto Pearson Intl - Chicago O'Hare Intl, Toronto Island - Chicago Midway and Toronto Pearson Intl - Chicago Midway.

  • What are the most reliable airlines from Toronto to Chicago?

    Consider EVA Air (94%), Egyptair (90%) or Copa Airlines (90%) when booking your flight. These represent the most reliable airlines when flying from Toronto to Chicago.

  • What are the cheapest flights from Toronto to Chicago?

    Looking for the cheapest flight from Toronto to Chicago? While on average our users pay $1,238, our data indicates the cheapest price to be $153. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around $153.

  • Can I find deals for flights from Toronto to Chicago that include hotel bookings?

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

  • How can I find direct flights from Toronto to Chicago?

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

  • Can I find deals for business class flights from Toronto to Chicago?

    Yes. Cheapflights offers flight deals from Toronto 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 to Chicago?

    Currently, June is the cheapest month in which you can book a flight from Toronto to Chicago (average of $83). Flying from Toronto to Chicago in February is currently the most expensive (average of $190). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
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Hammond
Porter
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Top 5 airlines flying from Toronto to Chicago

Discover the top 5 airlines that operate flights from Toronto 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 2,558,603 searches. Data last updated October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$147Average$272FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$158Average$327FlexibilityNo cancel feeOn-time52%
United AirlinesCheapest$165Average$288FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$344FlexibilityNo cancel feeOn-time71%
WestJetCheapest$208Average$348FlexibilityNo cancel feeOn-time60%

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