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San José

$120+ Cheap flights from Chicago (CHI) to San José (SJO)

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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Jun 20 — Jun 271
Sat 6/20
Sat 6/27
1 adult, Economy
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Find cheap flights from Chicago to San José 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 San José Juan Santamaria Intl are usually found in September or October, booked 6 days in advance, depart on a Tuesday or Monday and return on a Tuesday

Cheap flight deals from Chicago to San José

Cheapest flights from Chicago to San José
Explore the most affordable flight options available from Chicago to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 21, 2026.

This Air Canada deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/148:45 am
ORD
-
SJO
1 stop12h 50m
Air Canada
Mon 6/227:15 am
SJO
-
ORD
1 stop23h 35m
Air Canada
Deal found 5/17$434
This Air Canada deal was found by Cheapflights users on 5/16. 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 6/128:20 pm
ORD
-
SJO
1 stop26h 40m
Air Canada
Mon 6/157:15 am
SJO
-
ORD
2 stops23h 30m
Air Canada
Deal found 5/16$438
This Viva deal was found by Cheapflights users on 5/19. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/231:30 am
ORD
-
SJO
1 stop24h 45m
Viva
Fri 8/142:20 am
SJO
-
ORD
1 stop21h 20m
Viva
Deal found 5/19$441
This Air Canada deal was found by Cheapflights users on 5/20. 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.
Sun 5/248:45 am
ORD
-
SJO
1 stop12h 50m
Air Canada
Sat 5/307:15 am
SJO
-
ORD
2 stops23h 45m
Air Canada
Deal found 5/20$442
This Viva deal was found by Cheapflights users on 5/17. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/311:30 am
ORD
-
SJO
1 stop24h 45m
Viva
Fri 8/72:20 am
SJO
-
ORD
1 stop21h 20m
Viva
Deal found 5/17$445
This Air Canada deal was found by Cheapflights users on 5/20. 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.
Sat 5/236:22 pm
ORD
-
SJO
2 stops27h 13m
Air Canada
Sat 5/307:15 am
SJO
-
ORD
2 stops23h 45m
Air Canada
Deal found 5/20$447
This Volaris deal was found by Cheapflights users on 5/17. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/142:53 am
ORD
-
SJO
1 stop22h 06m
Multiple Airlines
Tue 9/224:15 pm
SJO
-
ORD
1 stop18h 54m
Multiple Airlines
Deal found 5/17$450
This Air Canada deal was found by Cheapflights users on 5/16. 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 6/128:20 pm
ORD
-
SJO
1 stop26h 40m
Air Canada
Mon 6/227:15 am
SJO
-
ORD
2 stops29h 51m
Air Canada
Deal found 5/16$452
This Southwest deal was found by Cheapflights users on 5/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:20 am
MDW
-
SJO
2 stops11h 20m
Southwest
Tue 9/19:00 am
SJO
-
MDW
2 stops11h 50m
Southwest
Deal found 5/19$453
This Ovago deal was found by Cheapflights users on 5/20. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am
ORD
-
SJO
1 stop6h 55m
JetBlue
Wed 9/162:05 pm
SJO
-
ORD
1 stop8h 39m
JetBlue
Deal found 5/20$455
This JetBlue deal was found by Cheapflights users on 5/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 am
ORD
-
SJO
1 stop6h 55m
JetBlue
Fri 9/182:05 pm
SJO
-
ORD
1 stop8h 39m
JetBlue
Deal found 5/20$460
This Delta deal was found by Cheapflights users on 5/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:00 am
MDW
-
SJO
1 stop6h 58m
Delta
Thu 10/221:23 pm
SJO
-
MDW
1 stop7h 22m
Delta
Deal found 5/20$482

Find flight deals from Chicago to San José

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San José (SJO). 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 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$434
(Air Canada)

One-way from

$120
(Super.com)

Popular in

December

Cheapest in

September

Average price

$535

Good round-trip deal

$497 or less

Good one-way deal

$434 or less
Provider with most accurate pricing for Chicago (CHI)-San José Juan Santamaria Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-San José Juan Santamaria Intl flights.
Search Deals
From Chicago (CHI) to San José Juan Santamaria Intl
Search Deals
One-way flight from Chicago (CHI) to San José Juan Santamaria Intl
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 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 San José Juan Santamaria Intl.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to San José Juan Santamaria Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to San José 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 21, 2026.
Use the filters below to find and compare flights from Chicago to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 7/31

1:30 am-1:15 am

1 stop24h 45m

San José Juan Santamaria Intl

Fri 8/7

2:20 am-12:40 am

1 stop21h 20m

$445

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 8/16

3:21 pm-7:10 am

1 stop16h 49m

San José Juan Santamaria Intl

Wed 8/19

4:08 am-1:59 pm

1 stop8h 51m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 7/1

3:21 pm-8:21 am

1 stop18h 00m

San José Juan Santamaria Intl

Mon 7/6

4:08 am-1:57 pm

1 stop8h 49m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 7/9

3:21 pm-7:12 am

1 stop16h 51m

San José Juan Santamaria Intl

Thu 7/16

10:03 am-4:00 am

1 stop16h 57m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 7/26

8:02 am-7:12 am

1 stop24h 10m

San José Juan Santamaria Intl

Tue 8/4

5:55 pm-1:59 pm

1 stop19h 04m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 7/9

3:21 pm-7:12 am

1 stop16h 51m

San José Juan Santamaria Intl

Fri 7/17

8:30 am-12:01 am

1 stop14h 31m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 7/31

3:21 pm-7:10 am

1 stop16h 49m

San José Juan Santamaria Intl

Sat 8/8

5:45 am-12:02 am

1 stop17h 17m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 7/6

3:21 pm-9:06 am

1 stop18h 45m

San José Juan Santamaria Intl

Tue 7/14

4:08 am-12:01 am

1 stop18h 53m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 7/31

1:20 am-8:19 am

1 stop7h 59m

San José Juan Santamaria Intl

Mon 8/31

10:03 am-1:02 am

1 stop13h 59m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 10/5

7:55 pm-11:58 am

1 stop17h 03m

San José Juan Santamaria Intl

Wed 10/21

1:23 pm-11:50 pm

1 stop9h 27m

$482

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/19

Showing 1-10 of 47 resultsSorted by cheapest first
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Compare providers for flights from Chicago to San José

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

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

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

Currently, August is the cheapest month in which you can book a flight from Chicago to San José (average of $88). Flying from Chicago to San José in December is currently the most expensive (average of $2,882). 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 SJO?

Find hourly flight availability from Chicago to San José. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 21, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to San José as you normally would.

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

What’s the top layover airport for flights from Chicago to San José?

Share of 1-stop round-trip flights from Chicago to San José chosen by Cheapflights users in the past 12 months, using the same layover each way.

Panama City (PTY) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to San José on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to San José?

Average round-trip fare for 1-stop flights from Chicago to San José, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Fort Lauderdale (FLL) is the most affordable 1-stop option, with an average round-trip price of $371.

What’s the fastest layover option from Chicago to San José?

Shortest average travel time for 1-stop one-way flights from Chicago to San José, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Fort Lauderdale (FLL) have the shortest average one-way travel time for 1-stop routes: 7h 06m.

Which airport typically offers the quickest layover for flights from Chicago to San José?

Average layover duration for 1-stop one-way flights from Chicago to San José, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Panama City (PTY) offer the fastest connection on this route, with an average layover time of 1h 29m.

How often are flights from Chicago to San José delayed?

About 20% of weekly flights between Chicago and San José have experienced delays in the past year, with the average delay time being 158 minutes.

What is the most punctual flight time for Chicago to San José 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?

Saturday 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 San José flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.

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

The price you pay for your flight from Chicago to San José may vary depending on when you book. For the best chance of a lower fare, look to book 13 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Reviews of airlines servicing San José

Get insights into the airlines that provide service to San José. 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 San José. Reviews last updated May 21, 2026.
Read through reviews of airlines operating flights from Chicago to San José, such as Southwest,Copa Airlines, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,282 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,282 reviews
Southwest
7.9
Good
4,282 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Copa Airlines
7.5
Good
1,577 reviews
Southwest
7.9
Good
4,282 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,748 reviews
Southwest
7.9
Good
4,282 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,641 reviews
Southwest
7.9
Good
4,282 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.2
Okay
8,609 reviews
Southwest
7.9
Good
4,282 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Chicago to San José. 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 San José from Chicago?

    Located just 8.8 mi from the city center, San José Juan Santamaria Intl is the airport most travelers will use when flying to San José from Chicago. Booking flights from Chicago to Juan Santamaria Intl (SJO) should be relatively easy as there are 0 daily inbound flights from Chicago from 10 different airlines.

  • How long is the flight from Chicago to San José?

    A quick flight from Chicago to San José can take about 6h 55m. JetBlue provides one of the quickest options available for as low as $460. Airlines will cover a distance of 2220 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to San José round-trip?

    Cheapflights users have booked flights from Chicago to San José round-trip from $139. Other airlines that can offer you cheap pricing are Delta, from $205, and Spirit Airlines, from $232. Avianca is currently priced 72% below the average price you’ll pay for this route.

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

    The cheapest airlines for a one-way flight from Chicago to San José are Spirit Airlines ($88), Frontier ($135), and Delta ($136).

  • What are the cheapest flights from Chicago to San José?

    The cheapest flight price from Chicago to San José is $165. On average you can expect to pay $544. The most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), can usually be booked for $428.

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

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

  • How can I find direct flights from Chicago to San José?

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

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

    Yes. Cheapflights offers flight deals from Chicago to San José 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 San José?

    Currently, August is the cheapest month in which you can book a flight from Chicago to San José (average of $88). Flying from Chicago to San José in December is currently the most expensive (average of $2,882). 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 San José?

Book flights to San José if you plan to visit one of these locations
Alajuela
Monteverde
Jacó
Heredia
Dominical
Manuel Antonio

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Top 10 airlines flying from Chicago to San José

Discover the top 10 airlines that operate flights from Chicago to San José. 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 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
AviancaCheapest$139Average$432FlexibilityNo cancel feeOn-time71%
DeltaCheapest$205Average$482FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$232Average$358FlexibilityNo cancel feeOn-time65%
FrontierCheapest$271Average$796FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$303Average$475FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$341Average$564FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$383Average$579FlexibilityNo cancel feeOn-time69%
GOLCheapest$384Average$788FlexibilityNo cancel feeOn-time74%
SouthwestCheapest$386Average$540FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$628Average$661FlexibilityNo cancel feeOn-time67%

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