Chicago

$131+ Cheap flights from Pearson Intl (YYZ) 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Apr 2 — Apr 91
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Find cheap flights from Pearson Intl to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
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Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago are usually found in April or July, booked 88 days in advance, depart on a Friday or Thursday and return on a Friday

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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(Ticket)

One-way from

$131
(Mytrip)

Popular in

December

Cheapest in

April

Average price

$296

Good round-trip deal

$294 or less

Good one-way deal

$182 or less
Provider with most accurate pricing for Toronto Pearson Intl-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Toronto Pearson Intl-Chicago (CHI) flights.
From Toronto Pearson Intl to Chicago (CHI)
One-way flight from Toronto Pearson Intl to Chicago (CHI)
Highest demand for flights based on searches. 5% potential increase in price ($16 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Average for round-trip flights in March 2025
Price to beat on a round-trip flight from Toronto Pearson Intl to Chicago (CHI).
Price to beat on a one-way flight from Toronto Pearson Intl to Chicago (CHI).

Find flight deals from Pearson Intl to Chicago

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 March 28, 2025.

This Ticket deal was found by Cheapflights users on 3/27. 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 Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/192:45 pmYYZ - ORD
Nonstop2h 06mAir Canada
Sun 4/207:20 amORD - YYZ
1 stop5h 19mAir Canada
Deal found 3/27$207
This Delta deal was found by Cheapflights users on 3/26. 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.
Wed 4/2312:54 pmYYZ - MDW
1 stop5h 25mDelta
Wed 4/305:59 pmMDW - YYZ
1 stop3h 56mDelta
Deal found 3/26$224
This United deal was found by Cheapflights users on 3/27. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1411:00 amYYZ - ORD
Nonstop2h 01mMultiple Airlines
Sun 6/158:25 pmORD - YYZ
Nonstop1h 42mMultiple Airlines
Deal found 3/27$227
This Delta deal was found by Cheapflights users on 3/26. 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 4/199:45 amYYZ - ORD
1 stop7h 26mDelta
Thu 5/17:10 amORD - YYZ
1 stop9h 49mDelta
Deal found 3/26$239
This United Airlines deal was found by Cheapflights users on 3/27. 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.
Sat 4/195:30 pmYYZ - ORD
Nonstop2h 00mUnited Airlines
Sat 4/2612:59 pmORD - YYZ
Nonstop1h 47mUnited Airlines
Deal found 3/27$251
This American Airlines deal was found by Cheapflights users on 3/27. 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 4/196:20 pmYYZ - ORD
Nonstop1h 55mAmerican Airlines
Sun 4/208:27 amORD - YYZ
1 stop5h 28mAmerican Airlines
Deal found 3/27$261
This Cheapflightsfares deal was found by Cheapflights users on 3/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/179:49 amYYZ - ORD
1 stop7h 41mWestJet
Sun 8/311:55 pmORD - YYZ
2 stops15h 17mWestJet
Deal found 3/28$291
This FlightHub deal was found by Cheapflights users on 3/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/306:30 amYYZ - MDW
1 stop11h 49mWestJet
Fri 5/210:20 amMDW - YYZ
1 stop11h 55mWestJet
Deal found 3/27$291
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/107:25 pmYYZ - MDW
1 stop10h 58mMultiple Airlines
Wed 4/163:00 pmMDW - YYZ
1 stop7h 54mMultiple Airlines
Deal found 3/27$333
This Kissandfly.com deal was found by Cheapflights users on 3/27. 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.
Mon 4/71:15 pmYYZ - ORD
Nonstop1h 55mBritish Airways
Thu 4/109:55 amORD - YYZ
Nonstop1h 40mBritish Airways
Deal found 3/27$343

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 2,558,603 searches. Data last updated March 28, 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

Sat 4/19

2:45 pm-3:51 pm

Nonstop2h 06m

Chicago O'Hare Intl

Sun 4/20

7:20 am-1:39 pm

1 stop5h 19m

$207

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 4/23

12:54 pm-5:19 pm

1 stop5h 25m

Chicago Midway

Wed 4/30

5:59 pm-10:55 pm

1 stop3h 56m

$224

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 6/14

11:00 am-12:01 pm

Nonstop2h 01m

Chicago O'Hare Intl

Sun 6/15

8:25 pm-11:07 pm

Nonstop1h 42m

$227

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 4/19

9:45 am-4:11 pm

1 stop7h 26m

Chicago O'Hare Intl

Thu 5/1

7:10 am-5:59 pm

1 stop9h 49m

$239

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 4/19

5:30 pm-6:30 pm

Nonstop2h 00m

Chicago O'Hare Intl

Sat 4/26

12:59 pm-3:46 pm

Nonstop1h 47m

$251

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 4/19

6:20 pm-7:15 pm

Nonstop1h 55m

Chicago O'Hare Intl

Sun 4/20

8:27 am-2:55 pm

1 stop5h 28m

$261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 5/17

9:49 am-4:30 pm

1 stop7h 41m

Chicago O'Hare Intl

Sun 8/31

1:55 pm-6:12 am

2 stops15h 17m

$291

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 4/30

6:30 am-5:19 pm

1 stop11h 49m

Chicago Midway

Fri 5/2

10:20 am-11:15 pm

1 stop11h 55m

$291

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 4/10

7:25 pm-5:23 am

1 stop10h 58m

Chicago Midway

Wed 4/16

3:00 pm-11:54 pm

1 stop7h 54m

$333

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 4/7

1:15 pm-2:10 pm

Nonstop1h 55m

Chicago O'Hare Intl

Thu 4/10

9:55 am-12:35 pm

Nonstop1h 40m

$343

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/28

Showing 1-10 of 20 results
1
2

Compare providers for flights from Pearson Intl 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 Pearson Intl to Chicago in March.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice 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 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 flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto Pearson Intl Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto Pearson Intl Airport-Chicago 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 flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for Toronto Pearson Intl Airport 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 Pearson Intl Airport to Chicago trip
Airlines
British Airways

BA's Club Suite offers privacy with solo pods and a door you can close.


BA's World Traveller Plus offers extra seat width and legroom for added comfort.

Air Canada

Air Canada offers free texting via Apple iMessage, WhatsApp, and Facebook Messenger for Aeroplan Members.


Families with kids under 6 get early boarding on Air Canada flights.

Read more about Air Canadaby Jessica Macdonald
United Airlines

Basic Economy allows a personal item only; no carry-on bags unless exceptions apply.


United First offers priority perks and two free checked bags on domestic routes.

Airports
YYZ

Security lines at YYZ are efficient and fast. Arrive early for US-bound flights to clear customs smoothly.

Read more about YYZby Kaitlyn McInnis
ORD

For a quick city transfer, take the 'L' train from ORD to downtown Chicago, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
Our travel experts
Gabriel Leigh

Gabriel Leigh

Expert on British Airways

Gabriel Leigh

Gabriel Leigh

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more
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 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 March 21, 2025.

Booking 88 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 $245). Flying from Toronto Pearson Intl Airport to Chicago in March is currently the most expensive (average of $323). 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 March 28, 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 52% on the cost of your flight, compared to a flight in the afternoon.

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 June 30, 2024.

Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Tuesday afternoons 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 March 28, 2025.

The most flights from YYZ to CHI are scheduled on a Thursday (53 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 March 28, 2025.
Get a feel of what it's like to fly with Delta, United Airlines and American Airlines from Toronto to Chicago by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
8.0
Very good
8.0
Very good

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
8.0
Very good

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
8.0
Very good

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
8.0
Very good

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
8.0
Very good

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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

    Currently priced at $207, Air Canada will fly you from Toronto Pearson Intl Airport to Chicago and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and United Airlines - these airlines can fly you to your destination from $224 and $251, respectively. Air Canada is 30% cheaper than the average price of flights available within the next 90 days to this destination.

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

    The cheapest airlines for a one-way flight from Toronto Pearson Intl Airport to Chicago are Air Canada ($134), United Airlines ($139), and Delta ($139).

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

    Consider Copa Airlines (88%), Emirates (87%) or ANA (86%) when booking your flight. These represent the most reliable airlines when flying from Toronto Pearson Intl Airport to Chicago.

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

    While on average a flight from Toronto Pearson Intl Airport to Chicago is generally $2,110, our data shows the cheapest flight currently is $119. When looking at the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), you can expect to pay $227 for that flight.

  • 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 $245). Flying from Toronto Pearson Intl Airport to Chicago in March is currently the most expensive (average of $323). 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 4 airlines flying from Pearson Intl to Chicago

Discover the top 4 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 2,558,603 searches. Data last updated March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$194Average$229FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$203Average$292FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$233Average$310FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$236Average$327FlexibilityNo cancel feeOn-time71%
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