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Pearson Intl

$75+ Cheap flights from Chicago (CHI) to Pearson Intl (YYZ)

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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Toronto Pearson Intl are usually found in June or July, booked 68 days in advance, depart on a Thursday or Friday and return on a Saturday

Cheap flight deals from Chicago to Pearson Intl

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Pearson Intl (YYZ). 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 September 11, 2025.

Round-trip from

$189
(Flightnetwork)

One-way from

$75
(Mytrip)

Popular in

December

Cheapest in

June

Average price

$307

Good round-trip deal

$270 or less

Good one-way deal

$212 or less
From Chicago (CHI) to Toronto Pearson Intl
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One-way flight from Chicago (CHI) to Toronto Pearson Intl
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Highest demand for flights based on searches. 7% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Toronto Pearson Intl.
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Price to beat on a one-way flight from Chicago (CHI) to Toronto Pearson Intl.
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Find flight deals from Chicago to Pearson Intl

Cheapest flights from Chicago to Pearson Intl
Explore the most affordable flight options available from Chicago to Pearson Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Flightnetwork deal was found by Cheapflights users on 9/9. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/309:55 amORD - YYZ
Nonstop1h 42mAir Canada
Thu 10/28:15 amYYZ - ORD
Nonstop1h 54mAir Canada
Deal found 9/9$189
This Mytrip deal was found by Cheapflights users on 9/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/410:40 amORD - YYZ
1 stop5h 44mAir Canada
Sun 10/56:15 amYYZ - ORD
1 stop4h 36mAir Canada
Deal found 9/9$194
This Mytrip deal was found by Cheapflights users on 9/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/207:43 pmORD - YYZ
1 stop17h 22mMultiple Airlines
Thu 10/236:30 amYYZ - ORD
1 stop10h 34mMultiple Airlines
Deal found 9/9$196
This Mytrip deal was found by Cheapflights users on 9/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:44 pmORD - YYZ
1 stop18h 21mMultiple Airlines
Tue 9/306:30 amYYZ - ORD
1 stop12h 09mMultiple Airlines
Deal found 9/9$199
This Mytrip deal was found by Cheapflights users on 9/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/217:43 pmORD - YYZ
1 stop17h 22mMultiple Airlines
Thu 10/236:30 amYYZ - ORD
1 stop10h 34mMultiple Airlines
Deal found 9/9$200
This Trip.com deal was found by Cheapflights users on 9/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/212:52 pmORD - YYZ
Nonstop1h 54mUnited Airlines
Sun 10/57:00 amYYZ - ORD
Nonstop1h 58mUnited Airlines
Deal found 9/9$201
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/19:20 pmORD - YYZ
1 stop11h 44mUnited Airlines
Thu 10/21:00 pmYYZ - ORD
Nonstop2h 01mUnited Airlines
Deal found 9/9$205
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/235:05 amORD - YYZ
1 stop8h 00mMultiple Airlines
Mon 10/274:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Deal found 9/9$207
This Mytrip deal was found by Cheapflights users on 9/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/285:05 amORD - YYZ
1 stop8h 00mMultiple Airlines
Tue 9/306:30 amYYZ - ORD
1 stop12h 09mMultiple Airlines
Deal found 9/9$210
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/210:11 amORD - YYZ
1 stop9h 56mMultiple Airlines
Sun 10/54:00 pmYYZ - ORD
1 stop26h 16mMultiple Airlines
Deal found 9/9$211
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/41:43 pmMDW - YYZ
1 stop8h 37mDelta
Wed 10/812:15 pmYYZ - MDW
1 stop7h 10mDelta
Deal found 9/10$244
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:00 pmMDW - YYZ
1 stop7h 18mDelta
Tue 10/146:15 amYYZ - MDW
1 stop3h 25mDelta
Deal found 9/9$277

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Pearson Intl 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 September 11, 2025.
Use the filters below to find and compare flights from Chicago to Toronto Pearson Intl Airport that are best for you.

Fly from

Chicago

Fly to

Pearson Intl

Route

Depart

Return

Price

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 10/8

7:10 am-9:58 am

Nonstop1h 48m

Toronto Pearson Intl

Sun 10/12

9:00 am-9:55 am

Nonstop1h 55m

$219

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 10/7

12:52 pm-3:46 pm

Nonstop1h 54m

Toronto Pearson Intl

Wed 10/8

9:00 am-9:55 am

Nonstop1h 55m

$219

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 11/7

1:19 pm-4:02 pm

Nonstop1h 43m

Toronto Pearson Intl

Mon 11/10

9:00 am-10:05 am

Nonstop2h 05m

$219

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 11/6

4:50 pm-7:45 pm

Nonstop1h 55m

Toronto Pearson Intl

Sat 11/8

9:00 am-10:05 am

Nonstop2h 05m

$219

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 10/21

12:52 pm-3:46 pm

Nonstop1h 54m

Toronto Pearson Intl

Thu 10/23

7:00 am-7:58 am

Nonstop1h 58m

$219

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 10/14

9:20 pm-10:04 am

1 stop11h 44m

Toronto Pearson Intl

Thu 10/16

9:00 am-9:55 am

Nonstop1h 55m

$229

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 10/7

8:50 am-2:19 pm

1 stop4h 29m

Toronto Pearson Intl

Tue 10/14

9:00 pm-10:07 pm

Nonstop2h 07m

$229

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sun 11/9

8:50 am-11:46 pm

1 stop13h 56m

Toronto Pearson Intl

Mon 11/10

9:00 pm-10:05 pm

Nonstop2h 05m

$229

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sun 10/5

10:45 am-5:14 pm

1 stop5h 29m

Toronto Pearson Intl

Tue 10/7

9:00 am-9:55 am

Nonstop1h 55m

$229

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 10/14

9:12 pm-11:58 pm

Nonstop1h 46m

Toronto Pearson Intl

Mon 10/20

12:45 pm-7:58 pm

1 stop8h 13m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 48 results
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The best insider tips for Chicago to Toronto Pearson Intl Airport 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 Chicago to Toronto Pearson Intl Airport trip
Airlines
Air Canada

Economy Latitude offers priority check-in and two checked bags, ideal for efficient travel.


Preferred Seats offer up to four inches extra space, bookable for a fee in any fare class.

Read more about Air Canadaby Jessica Macdonald
United Airlines

Basic Economy allows no carry-on bags, except for Premier members or select routes.


United Club lounges offer healthy snacks and comfortable seating, enhancing travel experience.

Read more about United Airlinesby Harriet Baskas
Airports
ORD

For a quick departure from ORD, use the “L” train to avoid traffic delays and reach the airport efficiently.

Read more about ORDby Ramsey Qubein
YYZ

Upon arrival at YYZ, consider using public transportation to avoid traffic and save money on your trip to downtown Toronto.

Read more about YYZby Kaitlyn McInnis
Our travel experts
Jessica Macdonald

Jessica Macdonald

Expert on Air Canada

Jessica Macdonald

Jessica Macdonald

Currently based in Scotland after living in South Africa and the United States, Jessica has been writing travel and aviation content for more than 10 years. She regularly contributes to Travel + Leisure and TripSavvy, and has had work published by Condé Nast Traveller and The Independent. She has traveled to more than 50 countries across six continents.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
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

Best time to book a flight from Chicago to Pearson Intl

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Pearson Intl. Price data was last updated on August 29, 2025.

The price you pay for your flight from Chicago to Toronto Pearson Intl Airport may vary depending on when you book. For the best chance of a lower fare, look to book 68 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Toronto Pearson Intl Airport (average of $243). Flying from Chicago to Toronto Pearson Intl Airport in August is currently the most expensive (average of $348). 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 CHI to YYZ?

Find hourly flight availability from Chicago to Pearson Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

One of the essential ways to save on airfare from Chicago to Toronto Pearson Intl Airport is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 26% on airfare.

What is the cheapest day to fly from Chicago to Toronto Pearson Intl Airport?

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

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

Weekly flight availability from Chicago to Toronto Pearson Intl Airport

Explore weekly flight availability from Chicago to Pearson Intl. 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 September 11, 2025.

The most flights from CHI to YYZ are scheduled on a Thursday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 on average).

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

Reviews of airlines servicing Pearson Intl

Get insights into the airlines that provide service to Pearson Intl. 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 Pearson Intl. Reviews last updated September 11, 2025.
See what other customers who have flown with Porter Airlines, United Airlines, and American Airlines from Chicago to Toronto Pearson Intl Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
363 reviews

Food

7.6

Boarding

8.1

Overall

7.9

Entertainment

7.0

Crew

8.6

Comfort

7.9

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
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews

Food

7.6

Boarding

8.1

Overall

7.9

Entertainment

7.0

Crew

8.6

Comfort

7.9

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
8,937 reviews
Porter Airlines
7.9
Good
363 reviews

Food

7.6

Boarding

8.1

Overall

7.9

Entertainment

7.0

Crew

8.6

Comfort

7.9

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
10,000 reviews
Porter Airlines
7.9
Good
363 reviews

Food

7.6

Boarding

8.1

Overall

7.9

Entertainment

7.0

Crew

8.6

Comfort

7.9

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
10,000 reviews
Porter Airlines
7.9
Good
363 reviews

Food

7.6

Boarding

8.1

Overall

7.9

Entertainment

7.0

Crew

8.6

Comfort

7.9

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 Chicago to Pearson Intl. 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 Chicago to Toronto Pearson Intl Airport?

    A quick flight from Chicago to Toronto Pearson Intl Airport can take about 1h 48m. United Airlines provides one of the quickest options available for as low as $219. The distance from Chicago to Toronto Pearson Intl Airport is about 436 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Cheapflights users have booked flights from Chicago to Toronto Pearson Intl Airport round-trip from $118. Other airlines that can offer you cheap pricing are United Airlines, from $146, and American Airlines, from $221. You may be able to fly from Chicago to Toronto Pearson Intl Airport for 60% less than the average price by searching for these airlines.

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

    One-way options have recently been found by users for as low as $78 on Air Canada. Other airlines that offer cheap prices include United Airlines from $85 and Delta from $94 one-way.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Toronto Pearson Intl Airport on time: Qatar Airways (85%), Envoy Air (80%), SkyWest Airlines (80%).

  • What are the cheapest flights from Chicago to Toronto Pearson Intl Airport?

    Looking at all options, your cheapest flight can be booked for $74. While the most popular route (Chicago O'Hare Intl - Toronto Pearson Intl) can be booked for $202 on average, our data indicates $1,016 when flying from Chicago to Toronto Pearson Intl Airport.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Pearson Intl 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 Chicago to Toronto Pearson Intl Airport?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Toronto Pearson Intl Airport (average of $243). Flying from Chicago to Toronto Pearson Intl Airport in August is currently the most expensive (average of $348). 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 Toronto Pearson Intl Airport?

Book flights to Toronto Pearson Intl Airport if you plan to visit one of these locations
Brampton
Kitchener
Collingwood
Markham
Oakville
Brantford
Pickering
Lindsay
Peterborough
Barrie
Cambridge
Milton
Oshawa
Burlington
Owen Sound
Ajax
Vaughan
Richmond Hill
Gravenhurst
St. Catharines

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Top 3 airlines flying from Chicago to Pearson Intl

Discover the top 3 airlines that operate flights from Chicago to Pearson Intl. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$118Average$270FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$146Average$306FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$221Average$390FlexibilityNo cancel feeOn-time71%

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