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$132+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYC
Jul 20 — Jul 271
Mon 7/20
Mon 7/27
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 64 days in advance, depart on a Friday or Tuesday and return on a Friday

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 June 20, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Fri 10/1612:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 6/17$295
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Sun 10/259:00 am
YYC
-
ORD
Nonstop3h 35m
WestJet
Deal found 6/20$297
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Fri 9/2512:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 6/20$298
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Fri 9/1812:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 6/18$299
This Gotogate deal was found by Cheapflights users on 6/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:35 pm
ORD
-
YYC
1 stop8h 42m
Air Canada
Sat 10/36:30 am
YYC
-
ORD
1 stop7h 25m
Air Canada
Deal found 6/17$300
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Fri 9/2512:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 6/20$301
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Mon 9/2812:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 6/18$303
This Trip.com deal was found by Cheapflights users on 6/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Thu 9/1012:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 6/17$304
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Mon 9/1412:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 6/17$305
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
Tue 9/155:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Fri 9/1812:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 6/18$306
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:30 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Mon 9/1412:00 pm
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 6/18$307
This Delta deal was found by Cheapflights users on 6/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:47 pm
MDW
-
YYC
1 stop7h 45m
Delta
Tue 9/296:45 am
YYC
-
MDW
1 stop5h 22m
Delta
Deal found 6/19$352

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 June 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$295
(Kiwi.com)

One-way from

$132
(Kiwi.com)

Popular in

July

Cheapest in

January

Average price

$361

Good round-trip deal

$416 or less

Good one-way deal

$174 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
Highest demand for flights based on searches. 16% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 20, 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

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 8/13

7:45 pm-10:36 pm

Nonstop3h 51m

Calgary

Mon 8/17

6:00 am-11:59 pm

1 stop16h 59m

$344

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 9/18

7:45 pm-10:36 pm

Nonstop3h 51m

Calgary

Tue 9/22

6:00 am-6:32 pm

1 stop11h 32m

$344

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 10/16

5:00 am-1:53 pm

1 stop9h 53m

Calgary

Wed 10/21

7:30 am-4:58 pm

1 stop8h 28m

$349

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 10/16

3:50 pm-8:54 pm

1 stop6h 04m

Calgary

Wed 10/21

7:45 am-9:45 pm

2 stops13h 00m

$361

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 12/8

12:30 pm-11:13 pm

2 stops11h 43m

Calgary

Fri 12/11

7:45 am-4:50 pm

1 stop8h 05m

$364

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 7/1

8:40 am-11:32 am

Nonstop3h 52m

Calgary

Sat 7/11

6:00 am-9:39 pm

1 stop14h 39m

$375

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 8/7

5:00 am-6:10 pm

1 stop14h 10m

Calgary

Sat 8/15

7:45 pm-9:00 am

1 stop12h 15m

$376
Quickest round-trip

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 9/8

7:45 pm-10:36 pm

Nonstop3h 51m

Calgary

Tue 9/15

8:30 am-1:05 pm

Nonstop3h 35m

$404

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 8/24

7:45 pm-10:36 pm

Nonstop3h 51m

Calgary

Thu 8/27

8:30 am-1:05 pm

Nonstop3h 35m

$407

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 9/23

8:55 am-8:42 pm

2 stops12h 47m

Calgary

Tue 9/29

6:35 am-5:33 pm

1 stop9h 58m

$416

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/18

Showing 1-10 of 41 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 June.
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

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 $618). 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 June 20, 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 at noon could potentially save you up to 40% on airfare.

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 June 20, 2026.

The most flights from CHI to YYC are scheduled on a Tuesday (13 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (9 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 142 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.

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

The best time to book flights from Chicago to Calgary is 62 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 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 June 13, 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. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 June 20, 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
7.8
Good
8,421 reviews

Comfort

7.8

Food

7.2

Crew

8.5

Overall

7.8

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,421 reviews
Delta
7.8
Good
8,421 reviews

Comfort

7.8

Food

7.2

Crew

8.5

Overall

7.8

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
United Airlines
7.4
Good
9,865 reviews
Delta
7.8
Good
8,421 reviews

Comfort

7.8

Food

7.2

Crew

8.5

Overall

7.8

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
WestJet
7.2
Good
3,375 reviews
Delta
7.8
Good
8,421 reviews

Comfort

7.8

Food

7.2

Crew

8.5

Overall

7.8

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
American Airlines
7.1
Good
11,715 reviews
Delta
7.8
Good
8,421 reviews

Comfort

7.8

Food

7.2

Crew

8.5

Overall

7.8

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Air Canada
7.1
Good
11,227 reviews
Delta
7.8
Good
8,421 reviews

Comfort

7.8

Food

7.2

Crew

8.5

Overall

7.8

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 11 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 United Airlines and Delta fly from Chicago to Calgary in about 3h 51m. The time it takes to get you to your destination can typically vary by up to 7h 52m. Chicago and Calgary are separated by a distance of 1381 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 United Airlines. Our recent data shows that you can find tickets from as low as $108 on this airline. Additional options worth looking into are Delta and Air Canada, starting at $111 and $123 round-trip. United Airlines is 65% 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 $64. 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: Envoy Air (94%), Air Canada (83%), United Airlines (83%).

  • What are the cheapest flights from Chicago to Calgary?

    While on average a flight from Chicago to Calgary is generally $393, our data shows the cheapest flight currently is $123. When looking at the most popular route, (Chicago O'Hare Intl - Calgary), you can expect to pay $296 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 $618). 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

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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 June 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$108Average$397FlexibilityNo cancel feeOn-time69%
DeltaCheapest$111Average$215FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$123Average$306FlexibilityNo cancel feeOn-time67%
WestJetCheapest$132Average$272FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$231Average$447FlexibilityNo cancel feeOn-time71%

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