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Calgary

$107+ Cheap flights from Chicago (CHI) to Calgary (YYC)

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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYC
Jun 4 — Jun 111
Thu 6/4
Thu 6/11
1 adult, Economy
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Find cheap flights from Chicago to Calgary 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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3. Compare prices and book

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Cheapflights Tip: The best prices from Chicago to Calgary are usually found in January or October, booked 23 days in advance, depart on a Friday or Thursday and return on a Sunday

Cheap flight deals from Chicago to Calgary

Cheapest flights from Chicago to Calgary
Explore the most affordable flight options available from Chicago to Calgary. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.

This Kissandfly.com deal was found by Cheapflights users on 5/3. 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 5/257:44 pm
ORD
-
YYC
Nonstop3h 53m
Lufthansa
Tue 6/28:30 am
YYC
-
ORD
Nonstop3h 37m
Lufthansa
Deal found 5/3$242
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Fri 5/297:44 pm
ORD
-
YYC
Nonstop3h 53m
United Airlines
Mon 6/88:30 am
YYC
-
ORD
Nonstop3h 37m
United Airlines
Deal found 5/1$243
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Tue 5/266:00 am
ORD
-
YYC
1 stop16h 48m
United Airlines
Fri 5/296:00 am
YYC
-
ORD
1 stop15h 49m
United Airlines
Deal found 5/1$245
This Flightnetwork deal was found by Cheapflights users on 5/2. 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 7/145:35 pm
ORD
-
YYC
1 stop8h 46m
Air Canada
Tue 7/216:30 am
YYC
-
ORD
1 stop7h 25m
Air Canada
Deal found 5/2$247
This American Airlines deal was found by Cheapflights users on 5/1. 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 9/18:46 pm
ORD
-
YYC
Nonstop3h 43m
American Airlines
Wed 9/27:00 am
YYC
-
ORD
Nonstop3h 35m
American Airlines
Deal found 5/1$254
This Delta deal was found by Cheapflights users on 5/1. 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 5/271:59 pm
MDW
-
YYC
1 stop7h 31m
Delta
Sat 5/306:45 am
YYC
-
MDW
1 stop10h 11m
Delta
Deal found 5/1$256
This Delta deal was found by Cheapflights users on 5/1. 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.
Tue 5/2612:30 pm
ORD
-
YYC
1 stop9h 00m
Delta
Sun 5/317:45 am
YYC
-
ORD
1 stop10h 05m
Delta
Deal found 5/1$256
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Fri 5/297:44 pm
ORD
-
YYC
Nonstop3h 53m
United Airlines
Thu 6/116:00 am
YYC
-
ORD
1 stop13h 11m
United Airlines
Deal found 5/1$258
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Fri 5/297:44 pm
ORD
-
YYC
Nonstop3h 53m
United Airlines
Mon 6/18:30 am
YYC
-
ORD
Nonstop3h 37m
United Airlines
Deal found 5/1$259
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 5/225:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Mon 5/2512:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 5/2$260
This FlightHub deal was found by Cheapflights users on 5/1. 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.
Sat 5/305:30 pm
ORD
-
YYC
Nonstop3h 55m
Multiple Airlines
Sat 6/67:05 am
YYC
-
ORD
1 stop8h 13m
Multiple Airlines
Deal found 5/1$261
This Trip.com deal was found by Cheapflights users on 5/1. 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.
Tue 8/45:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Wed 8/1212:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 5/1$263

Find flight deals from Chicago to Calgary

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Calgary (YYC). 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 May 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$242
(Kissandfly.com)

One-way from

$107
(United Airlines)

Popular in

December

Cheapest in

January

Average price

$274

Good round-trip deal

$345 or less

Good one-way deal

$125 or less
Provider with most accurate pricing for Chicago (CHI)-Calgary flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Calgary flights.
Search Deals
From Chicago (CHI) to Calgary
Search Deals
One-way flight from Chicago (CHI) to Calgary
Search Deals
High demand for flights, 5% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Calgary.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Calgary.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Calgary 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 May 5, 2026.
Use the filters below to find and compare flights from Chicago to Calgary that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 5/16

9:22 am-8:30 pm

2 stops12h 08m

Calgary

Tue 5/19

6:45 am-5:56 pm

1 stop10h 11m

$266

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 5/27

12:30 pm-8:30 pm

1 stop9h 00m

Calgary

Fri 6/5

7:45 am-6:50 pm

1 stop10h 05m

$290

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 7/13

5:00 am-6:10 pm

1 stop14h 10m

Calgary

Mon 7/20

6:00 am-11:19 pm

1 stop16h 19m

$291

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 6/3

9:49 am-10:57 pm

2 stops14h 08m

Calgary

Tue 6/9

6:45 am-8:31 pm

2 stops12h 46m

$338

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 7/15

2:02 pm-10:58 pm

1 stop9h 56m

Calgary

Mon 7/20

7:45 am-6:57 pm

1 stop10h 12m

$357

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 5/23

1:59 pm-8:30 pm

1 stop7h 31m

Calgary

Sat 5/30

6:45 am-5:56 pm

1 stop10h 11m

$397

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 7/30

12:27 pm-8:35 pm

1 stop9h 08m

Calgary

Sat 8/1

6:45 am-5:26 pm

1 stop9h 41m

$409

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 6/2

8:42 am-10:57 pm

2 stops15h 15m

Calgary

Mon 6/8

7:40 am-6:58 pm

1 stop10h 18m

$412

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 6/5

12:47 pm-10:15 pm

1 stop10h 28m

Calgary

Thu 6/11

7:40 am-6:58 pm

1 stop10h 18m

$423

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 8/2

2:02 pm-10:58 pm

1 stop9h 56m

Calgary

Fri 8/7

7:45 am-6:19 pm

1 stop9h 34m

$436

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 43 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Calgary

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 Chicago to Calgary in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust 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 Chicago-Calgary flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Calgary flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Calgary flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Calgary 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 Chicago-Calgary 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 Chicago to Calgary

Have a flexible travel schedule? Discover the best time to fly to Calgary 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 Calgary

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

The best time to book flights from Chicago to Calgary is 52 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, November is the cheapest month in which you can book a flight from Chicago to Calgary (average of $60). Flying from Chicago to Calgary in September is currently the most expensive (average of $617). 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 YYC?

Find hourly flight availability from Chicago to Calgary. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 5, 2026.

One of the essential ways to save on airfare from Chicago to Calgary is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 38% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Calgary. Price data was last updated on May 2, 2026.

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

Weekly flight availability from Chicago to Calgary

Explore weekly flight availability from Chicago to Calgary. 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 May 5, 2026.

The most flights from CHI to YYC are scheduled on a Monday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

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

How often are flights from Chicago to Calgary delayed?

About 31% of weekly flights between Chicago and Calgary have experienced delays in the past year, with the average delay time being 140 minutes.

What is the most punctual flight time for Chicago to Calgary flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Calgary flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 27% of flights being delayed.

The best insider tips for Chicago to Calgary 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 Chicago to Calgary trip
Our travel experts
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
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
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
Jenna Scatena

Jenna Scatena

Expert on YYC

Journalist and Travel Writer, Jenna Scatena is an award-winning travel writer with a love for sharing stories and exploring new places, especially by Vespa. Though she's from San Francisco, she has spent a significant chunk of her vacation days over the last decade eating her way through Texas and sleeping in hotels around the world—especially in California, the Middle East, and Europe.

Read more

Reviews of airlines servicing Calgary

Get insights into the airlines that provide service to Calgary. 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 Calgary. Reviews last updated May 5, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andWestJet from Chicago to Calgary 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.
Delta
7.9
Good
8,460 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.9

Entertainment

7.8

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
Delta
7.9
Good
8,460 reviews
Delta
7.9
Good
8,460 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.9

Entertainment

7.8

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
United Airlines
7.4
Good
9,683 reviews
Delta
7.9
Good
8,460 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.9

Entertainment

7.8

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
WestJet
7.2
Good
3,331 reviews
Delta
7.9
Good
8,460 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.9

Entertainment

7.8

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
American Airlines
7.1
Good
11,669 reviews
Delta
7.9
Good
8,460 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.9

Entertainment

7.8

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
Air Canada
7.1
Good
10,999 reviews
Delta
7.9
Good
8,460 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.9

Entertainment

7.8

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Calgary. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Calgary from Chicago?

    Most people fly into Calgary (YYC) if they book a flight to Calgary from Chicago. On average, Calgary has 3 inbound flights from Chicago per day from 5 airlines. Calgary is conveniently located just 5.8 mi from Calgary’s city center.

  • How long is the flight from Chicago to Calgary?

    Airlines like Delta and United Airlines fly from Chicago to Calgary in about 12h 08m. The time it takes to get you to your destination can typically vary by up to 2h 02m. Chicago and Calgary are separated by a distance of 1396 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 Calgary round-trip?

    Our cheapest airline available from Chicago to Calgary is Air Canada. Our recent data shows that you can find tickets from as low as $74 on this airline. Additional options worth looking into are United Airlines and Delta, starting at $89 and $111 round-trip. Air Canada is 75% cheaper than the average price of flights available within the next 90 days to this destination.

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

    The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as $63. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Chicago to Calgary for a low price.

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

    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 Calgary on time: Air Canada (77%), United Airlines (77%), American Airlines (68%).

  • What are the cheapest flights from Chicago to Calgary?

    While on average a flight from Chicago to Calgary is generally $790, our data shows the cheapest flight currently is $101. When looking at the most popular route, (Chicago O'Hare Intl - Calgary), you can expect to pay $235 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Calgary 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 Calgary?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Calgary (average of $60). Flying from Chicago to Calgary in September is currently the most expensive (average of $617). 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 Calgary?

Book flights to Calgary if you plan to visit one of these locations
Canmore
Airdrie

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Calgary

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Calgary flights
Midway to Calgary flights
St. Louis to Calgary flights
O'Hare Intl to Edmonton flights
Springfield to Calgary flights
O'Hare Intl to Grande Prairie flights

Top 5 airlines flying from Chicago to Calgary

Discover the top 5 airlines that operate flights from Chicago to Calgary. 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 May 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$74Average$254FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$89Average$342FlexibilityNo cancel feeOn-time69%
DeltaCheapest$111Average$196FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$130Average$263FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$228Average$429FlexibilityNo cancel feeOn-time71%

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