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O'Hare Intl

$124+ Cheap flights from Pearson Intl (YYZ) to O'Hare Intl (ORD)

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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — ORD
May 23 — May 301
Sat 5/23
Sat 5/30
1 adult, Economy
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Find cheap flights from Pearson Intl to O'Hare Intl with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago O'Hare Intl are usually found in January or May, booked 68 days in advance, depart on a Friday or Saturday and return on a Thursday

Cheap flight deals from Pearson Intl to O'Hare Intl

Cheapest flights from Pearson Intl to O'Hare Intl
Explore the most affordable flight options available from Pearson Intl to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 23, 2026.

This Kissandfly.com deal was found by Cheapflights users on 4/21. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:50 am
YYZ
-
ORD
Nonstop2h 00m
Lufthansa
Sun 6/77:09 am
ORD
-
YYZ
Nonstop1h 45m
Lufthansa
Deal found 4/21$206
This Air Canada deal was found by Cheapflights users on 4/17. 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.
Sat 5/910:30 am
YYZ
-
ORD
1 stop5h 23m
Air Canada
Tue 5/129:55 am
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 4/17$208
This American Airlines deal was found by Cheapflights users on 4/19. 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 6/67:20 am
YYZ
-
ORD
Nonstop2h 10m
American Airlines
Sat 6/204:45 pm
ORD
-
YYZ
1 stop4h 45m
American Airlines
Deal found 4/19$209
This flygcity.se deal was found by Cheapflights users on 4/20. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/14:00 pm
YYZ
-
ORD
Nonstop1h 59m
Air Canada
Sun 6/77:09 am
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 4/20$211
This Mytrip deal was found by Cheapflights users on 4/22. 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 6/66:25 pm
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Sat 6/139:55 am
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 4/22$212
This TravelUp deal was found by Cheapflights users on 4/20. 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 TravelUp is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:40 pm
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Wed 5/62:15 pm
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 4/20$213
This United Airlines deal was found by Cheapflights users on 4/19. 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.
Thu 6/2511:00 am
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Sun 6/282:56 pm
ORD
-
YYZ
Nonstop2h 00m
United Airlines
Deal found 4/19$215
This Travelis deal was found by Cheapflights users on 4/20. 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 Travelis is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2112:25 pm
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Sun 5/249:55 am
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 4/20$221
This Trip.com deal was found by Cheapflights users on 4/19. 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 5/288:00 am
YYZ
-
ORD
1 stop13h 08m
Air Canada
Sun 5/318:35 pm
ORD
-
YYZ
Nonstop1h 43m
Air Canada
Deal found 4/19$222
This Kissandfly.com deal was found by Cheapflights users on 4/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:00 pm
YYZ
-
ORD
Nonstop2h 05m
Lufthansa
Sun 5/317:09 am
ORD
-
YYZ
Nonstop1h 45m
Lufthansa
Deal found 4/20$223

Find flight deals from Pearson Intl to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Pearson Intl (YYZ) to O'Hare Intl (ORD). 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 April 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$206
(Kissandfly.com)

One-way from

$124
(Trip.com)

Popular in

December

Cheapest in

January

Average price

$321

Good round-trip deal

$331 or less

Good one-way deal

$215 or less
Provider with most accurate pricing for Toronto Pearson Intl-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toronto Pearson Intl-Chicago O'Hare Intl flights.
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From Toronto Pearson Intl to Chicago O'Hare Intl
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One-way flight from Toronto Pearson Intl to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Toronto Pearson Intl to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Toronto Pearson Intl to Chicago O'Hare Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pearson Intl to O'Hare 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 April 23, 2026.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 5/19

5:20 pm-6:21 pm

Nonstop2h 01m

Chicago O'Hare Intl

Wed 7/8

7:09 am-9:54 am

Nonstop1h 45m

$215

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/28

5:15 pm-6:19 pm

Nonstop2h 04m

Chicago O'Hare Intl

Sun 5/31

7:09 am-9:54 am

Nonstop1h 45m

$229

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 6/6

7:00 am-8:00 am

Nonstop2h 00m

Chicago O'Hare Intl

Tue 6/9

3:53 pm-11:54 pm

1 stop7h 01m

$229

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 6/4

7:00 am-8:00 am

Nonstop2h 00m

Chicago O'Hare Intl

Sun 6/7

7:09 am-9:54 am

Nonstop1h 45m

$229

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/21

1:00 pm-2:06 pm

Nonstop2h 06m

Chicago O'Hare Intl

Sat 5/30

9:55 pm-10:04 am

1 stop11h 09m

$229
Quickest round-trip

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 6/30

8:50 am-9:50 am

Nonstop2h 00m

Chicago O'Hare Intl

Sat 7/4

9:15 pm-11:59 pm

Nonstop1h 44m

$231

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 6/6

12:09 pm-4:29 pm

1 stop5h 20m

Chicago O'Hare Intl

Tue 6/9

6:00 am-1:42 pm

1 stop6h 42m

$234

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 5/12

6:10 am-8:45 am

1 stop3h 35m

Chicago O'Hare Intl

Wed 5/13

10:45 am-5:59 pm

1 stop6h 14m

$234

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 5/5

6:11 pm-8:40 pm

1 stop3h 29m

Chicago O'Hare Intl

Fri 5/8

8:42 am-6:31 pm

1 stop8h 49m

$234

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 6/17

6:30 am-11:31 am

1 stop6h 01m

Chicago O'Hare Intl

Sat 6/20

7:01 am-1:34 pm

1 stop5h 33m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/20

Showing 1-10 of 22 resultsSorted by cheapest first
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3

Compare providers for flights from Pearson Intl to O'Hare Intl

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 Pearson Intl to O'Hare Intl in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust Score*1 star
Trip.comPrice Accuracy1 starTrust 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 Pearson Intl Airport-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toronto Pearson Intl Airport-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto Pearson Intl Airport-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto Pearson Intl Airport-Chicago O'Hare Intl Airport flights, Cheapflights users trust FlightHub the most. FlightHub 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 Pearson Intl Airport-Chicago O'Hare Intl Airport 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 Pearson Intl to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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 O'Hare Intl Airport

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

Use this chart to determine the optimal time to book a round-trip flight from Pearson Intl to O'Hare Intl. Price data was last updated on April 17, 2026.

Booking 68 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 O'Hare Intl Airport. 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 O'Hare Intl Airport?

Currently, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport (average of $255). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $331). 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 ORD?

Find hourly flight availability from Pearson Intl to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 23, 2026.

When flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 45% versus a flight in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Pearson Intl to O'Hare Intl. Price data was last updated on April 18, 2026.

Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight should consider departing on Friday 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.

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

The best insider tips for Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport trip
Our travel experts
Brandon Schultz

Brandon Schultz

Expert on Qatar Airways

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more
Jessica Macdonald

Jessica Macdonald

Expert on Air Canada

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 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

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 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 O'Hare Intl

Get insights into the airlines that provide service to O'Hare 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 O'Hare Intl. Reviews last updated April 23, 2026.
Peruse reviews from past customers who have flown with Porter Airlines,United Airlines, andAmerican Airlines from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport 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
435 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
435 reviews
Porter Airlines
8.0
Very good
435 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,635 reviews
Porter Airlines
8.0
Very good
435 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
American Airlines
7.1
Good
11,661 reviews
Porter Airlines
8.0
Very good
435 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
10,957 reviews
Porter Airlines
8.0
Very good
435 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

Related info for your journey

Find useful and relevant information for your journey from Pearson Intl to O'Hare 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 Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

    For as low as $215, United Airlines can have you in Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport in 2h 01m. The distance from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport is about 436 mi. All flights are typically nonstop.

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

    Flying on Air Canada is currently your cheapest option to Chicago O'Hare Intl Airport, with prices starting at $146. Additional round-trip tickets that might be worth considering are offered by United Airlines and American Airlines, with the lowest prices starting at $165 and $189, respectively. Users have found that Air Canada is 50% cheaper than the other options available to this destination.

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

    $108 is the cheapest one-way deal found within the past few days, from Air Canada. You may also be able to find cheap deals on United Airlines and Porter Airlines, with prices starting from $111 and $122, respectively.

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

    The top 3 most reliable airlines when flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport are Copa Airlines (91%), EVA Air (78%) and Republic Airways (73%).

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

    Looking for the cheapest flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport? While on average our users pay $560, our data indicates the cheapest price to be $128. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around $199.

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

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

  • How can I find direct flights from Pearson Intl to O'Hare Intl?

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

  • Can I find deals for business class flights from Pearson Intl to O'Hare Intl?

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

    Currently, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport (average of $255). Flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $331). 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 O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Rosemont
Schaumburg
Naperville
Gurnee
Lake Geneva
Delavan
Hoffman Estates
Downers Grove
Oakbrook Terrace
Benton Harbor
Des Plaines
Oak Brook
South Holland
Libertyville
Elgin
Warrenville
Elk Grove Village
Bridgeview
Great Lakes
Lansing

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Alternative routes for Pearson Intl to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
Hamilton to O'Hare Intl flights

Top 4 airlines flying from Pearson Intl to O'Hare Intl

Discover the top 4 airlines that operate flights from Pearson Intl to O'Hare 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 April 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$146Average$274FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$165Average$267FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$295FlexibilityNo cancel feeOn-time71%
Porter AirlinesCheapest$192Average$420FlexibilityNo cancel feeOn-time52%

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