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O'Hare Intl

$102+ Cheap flights from Calgary (YYC) 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — ORD
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Find cheap flights from Calgary to O'Hare Intl 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 Calgary to Chicago O'Hare Intl are usually found in May or April, booked 43 days in advance, depart on a Sunday or Friday and return on a Friday

Cheap flight deals from Calgary to O'Hare Intl

Cheapest flights from Calgary to O'Hare Intl
Explore the most affordable flight options available from Calgary to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/20. 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 3/69:00 am
YYC
-
ORD
Nonstop3h 35m
WestJet
Mon 3/92:20 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 1/20$165
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/69:00 am
YYC
-
ORD
Nonstop3h 35m
WestJet
Fri 3/132:20 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 1/20$172
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/209:00 am
YYC
-
ORD
Nonstop3h 35m
WestJet
Fri 2/272:20 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 1/21$183
This Air Canada deal was found by Cheapflights users on 1/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:00 am
YYC
-
ORD
1 stop8h 48m
Air Canada
Sat 2/282:00 pm
ORD
-
YYC
1 stop7h 44m
Air Canada
Deal found 1/21$186
This Trip.com deal was found by Cheapflights users on 1/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/65:35 am
YYC
-
ORD
1 stop8h 35m
Multiple Airlines
Fri 3/132:20 pm
ORD
-
YYC
Nonstop3h 55m
Multiple Airlines
Deal found 1/20$195
This Super.com deal was found by Cheapflights users on 1/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/69:00 am
YYC
-
ORD
Nonstop3h 35m
WestJet
Fri 3/62:20 pm
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 1/21$199
This Air Canada deal was found by Cheapflights users on 1/20. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/611:40 pm
YYC
-
ORD
1 stop8h 33m
Air Canada
Mon 3/93:55 pm
ORD
-
YYC
1 stop9h 04m
Air Canada
Deal found 1/20$203
This Air Canada deal was found by Cheapflights users on 1/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:40 pm
YYC
-
ORD
1 stop12h 21m
Air Canada
Sat 2/282:00 pm
ORD
-
YYC
1 stop7h 44m
Air Canada
Deal found 1/21$211
This Air Canada deal was found by Cheapflights users on 1/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:30 am
YYC
-
ORD
1 stop8h 40m
Air Canada
Sat 2/282:00 pm
ORD
-
YYC
1 stop7h 44m
Air Canada
Deal found 1/21$217
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:30 am
YYC
-
ORD
1 stop10h 31m
Delta
Fri 2/271:20 pm
ORD
-
YYC
1 stop10h 45m
Delta
Deal found 1/21$218
This Air Canada deal was found by Cheapflights users on 1/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/65:35 am
YYC
-
ORD
1 stop8h 35m
Air Canada
Sat 3/73:55 pm
ORD
-
YYC
1 stop9h 04m
Air Canada
Deal found 1/21$221

Find flight deals from Calgary to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) 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 January 21, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$165
(Kiwi.com)

One-way from

$102
(Kiwi.com)

Popular in

August

Cheapest in

May

Average price

$247

Good round-trip deal

$183 or less

Good one-way deal

$221 or less
Provider with most accurate pricing for Calgary-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Calgary-Chicago O'Hare Intl flights.
Search Deals
From Calgary to Chicago O'Hare Intl
Search Deals
One-way flight from Calgary to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($51 potential increase over avg. RT price).
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 January 2026
Search Deals
Price to beat on a round-trip flight from Calgary to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Calgary to Chicago O'Hare Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Calgary 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 January 21, 2026.
Use the filters below to find and compare flights from Calgary to Chicago O'Hare Intl Airport that are best for you.

Fly from

Calgary

Fly to

O'Hare Intl

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 3/6

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

Fri 3/13

2:20 pm-5:15 pm

Nonstop3h 55m

$172

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 3/10

7:40 am-11:54 pm

2 stops15h 14m

Chicago O'Hare Intl

Tue 3/17

1:19 pm-11:02 pm

1 stop10h 43m

$228

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 5/28

7:15 am-6:01 pm

1 stop9h 46m

Chicago O'Hare Intl

Tue 6/2

1:55 pm-11:06 pm

1 stop10h 11m

$228

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 4/21

6:40 am-3:14 pm

1 stop7h 34m

Chicago O'Hare Intl

Thu 4/23

1:22 pm-11:00 pm

1 stop10h 38m

$229

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 4/14

6:40 am-3:14 pm

1 stop7h 34m

Chicago O'Hare Intl

Thu 4/16

1:22 pm-11:00 pm

1 stop10h 38m

$229

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 3/6

7:00 am-5:44 pm

1 stop9h 44m

Chicago O'Hare Intl

Mon 3/9

2:20 pm-5:15 pm

Nonstop3h 55m

$244

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 5/15

7:15 am-6:01 pm

1 stop9h 46m

Chicago O'Hare Intl

Tue 5/19

1:55 pm-11:06 pm

1 stop10h 11m

$244

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 6/29

7:15 am-6:01 pm

1 stop9h 46m

Chicago O'Hare Intl

Tue 7/7

1:55 pm-11:06 pm

1 stop10h 11m

$245

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 2/6

6:30 am-3:19 pm

1 stop7h 49m

Chicago O'Hare Intl

Sun 2/8

8:50 am-11:02 pm

2 stops15h 12m

$261

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 2/6

5:35 am-3:10 pm

1 stop8h 35m

Chicago O'Hare Intl

Fri 3/6

6:25 pm-1:14 am

1 stop7h 49m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 22 results
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Compare providers for flights from Calgary 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 Calgary to O'Hare Intl in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
oojoPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust Score*1 star

*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 Calgary-Chicago O'Hare Intl Airport flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Calgary-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from Calgary-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Calgary-Chicago O'Hare Intl Airport flights, Cheapflights users trust CheapOair the most. CheapOair 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 Calgary-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 Calgary to O'Hare Intl

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

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

Use this chart to determine the optimal time to book a round-trip flight from Calgary to O'Hare Intl. Price data was last updated on January 16, 2026.

To ensure you get the cheapest price possible for a flight from Calgary to Chicago O'Hare Intl Airport, you should look to book at least 43 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Calgary to Chicago O'Hare Intl Airport?

Currently, April is the cheapest month in which you can book a flight from Calgary to Chicago O'Hare Intl Airport (average of $108). Flying from Calgary to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $155). 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 YYC to ORD?

Find hourly flight availability from Calgary 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 January 21, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Calgary to Chicago O'Hare Intl Airport as you normally would.

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

The best insider tips for Calgary 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 Calgary to Chicago O'Hare Intl Airport trip
Our travel experts
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 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 January 21, 2026.
Get a feel of what it's like to fly with United Airlines, American Airlines, and WestJet from Calgary to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,191 reviews

Entertainment

7.1

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,191 reviews
United Airlines
7.4
Good
9,191 reviews

Entertainment

7.1

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,174 reviews
United Airlines
7.4
Good
9,191 reviews

Entertainment

7.1

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,247 reviews
United Airlines
7.4
Good
9,191 reviews

Entertainment

7.1

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
10,646 reviews
United Airlines
7.4
Good
9,191 reviews

Entertainment

7.1

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Calgary 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.

  • What airport do you fly from for flights from Calgary to Chicago O'Hare Intl?

    For a flight from Calgary to Chicago O'Hare Intl, you will be flying from Calgary. Calgary (YYC) is just 5.8 mi from the center of the city. Calgary is the only Calgary airport and it handles 7 outbound flights to Chicago O'Hare Intl per day. 4 airlines have flights to Chicago O'Hare Intl from Calgary on a regular basis.

  • How long is the flight from Calgary to Chicago O'Hare Intl Airport?

    Departing from Calgary to Chicago O'Hare Intl Airport will take you 8h 35m. There are 1381 mi between Calgary and Chicago O'Hare Intl Airport. 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 Calgary to Chicago O'Hare Intl Airport round-trip?

    Our cheapest airline available from Calgary to Chicago O'Hare Intl Airport is Air Canada. Our recent data shows that you can find tickets from as low as $101 on this airline. Additional options worth looking into are WestJet and American Airlines, starting at $137 and $185 round-trip. You may be able to fly from Calgary to Chicago O'Hare Intl Airport for 60% less than the average price by searching for these airlines.

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

    $94 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on American Airlines and Air Canada, with prices starting from $102 and $112, respectively.

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

    The top 3 most reliable airlines when flying from Calgary to Chicago O'Hare Intl Airport are WestJet (77%), Delta (76%) and Air Canada (65%).

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

    Looking for the cheapest flight from Calgary to Chicago O'Hare Intl Airport? While on average our users pay $363, our data indicates the cheapest price to be $116. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $175.

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

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

  • How can I find direct flights from Calgary 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 Calgary to O'Hare Intl.

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

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

    Currently, April is the cheapest month in which you can book a flight from Calgary to Chicago O'Hare Intl Airport (average of $108). Flying from Calgary to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $155). 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
Schaumburg
Rosemont
Naperville
Gurnee
Elgin
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Libertyville
Lake Geneva
Bridgeview
Kenosha
Warrenville
Waukegan
Aurora

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Alternative routes for Calgary to O'Hare Intl

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

Top 4 airlines flying from Calgary to O'Hare Intl

Discover the top 4 airlines that operate flights from Calgary 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$101Average$335FlexibilityNo cancel feeOn-time67%
WestJetCheapest$137Average$237FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$185Average$376FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$186Average$457FlexibilityNo cancel feeOn-time69%

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