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$203+ Cheap flights from Chicago (CHI) to Sao Paulo, Brazil (SAO)

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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAO
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Sao Paulo are usually found in January or March, booked 10 days in advance, depart on a Thursday or Saturday and return on a Monday

Cheap flight deals from Chicago to Sao Paulo

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Sao Paulo (SAO). 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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$471
(MaxMilhas)

One-way from

$203
(Arajet)

Popular in

December

Cheapest in

January

Average price

$796

Good round-trip deal

$517 or less

Good one-way deal

$516 or less
Provider with most accurate pricing for Chicago (CHI)-Sao Paulo (SAO) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Sao Paulo (SAO) flights.
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From Chicago (CHI) to Sao Paulo (SAO)
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One-way flight from Chicago (CHI) to Sao Paulo (SAO)
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 4% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Sao Paulo (SAO).
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Price to beat on a one-way flight from Chicago (CHI) to Sao Paulo (SAO).
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Find flight deals from Chicago to Sao Paulo

Cheapest flights from Chicago to Sao Paulo
Explore the most affordable flight options available from Chicago to Sao Paulo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.

This MaxMilhas deal was found by Cheapflights users on 10/12. 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 MaxMilhas is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/132:05 pmORD - GRU
1 stop23h 10mGOL
Mon 11/177:35 amGRU - ORD
1 stop31h 40mGOL
Deal found 10/12$471
This Mytrip deal was found by Cheapflights users on 10/12. 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.
Wed 11/265:45 amORD - GRU
1 stop13h 35mMultiple Airlines
Wed 12/311:59 pmGRU - ORD
2 stops21h 37mMultiple Airlines
Deal found 10/12$472
This Flightnetwork deal was found by Cheapflights users on 10/13. 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 10/2811:20 pmORD - GRU
1 stop21h 20mAvianca
Thu 11/62:40 amGRU - ORD
1 stop20h 40mAvianca
Deal found 10/13$476
This Booking.com deal was found by Cheapflights users on 10/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/210:20 pmORD - GRU
1 stop24h 15mAvianca
Tue 11/112:40 amGRU - ORD
1 stop20h 40mAvianca
Deal found 10/12$477
This FlightHub deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2911:20 pmORD - GRU
1 stop21h 20mAvianca
Mon 11/101:20 amGRU - ORD
1 stop22h 00mAvianca
Deal found 10/11$478
This GOL deal was found by Cheapflights users on 10/13. 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 GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/71:35 pmORD - GRU
1 stop33h 00mGOL
Mon 11/177:35 amGRU - ORD
1 stop31h 40mGOL
Deal found 10/13$479
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Wed 11/125:50 pmORD - GRU
Nonstop10h 25mUnited Airlines
Wed 11/199:45 pmGRU - ORD
Nonstop10h 45mUnited Airlines
Deal found 10/14$483
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Wed 11/1211:46 amORD - GRU
1 stop17h 24mAmerican Airlines
Sat 11/2210:35 pmGRU - ORD
1 stop15h 16mAmerican Airlines
Deal found 10/12$485
This GOL deal was found by Cheapflights users on 10/13. 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 GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/91:35 pmORD - GRU
1 stop23h 40mGOL
Mon 11/177:35 amGRU - ORD
1 stop31h 40mGOL
Deal found 10/13$486
This Copa Airlines deal was found by Cheapflights users on 10/12. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/287:59 amORD - GRU
1 stop14h 11mCopa Airlines
Sun 11/23:10 amGRU - ORD
1 stop23h 55mCopa Airlines
Deal found 10/12$488
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Sun 11/169:00 amORD - GRU
1 stop22h 20mUnited Airlines
Wed 11/269:45 pmGRU - ORD
Nonstop10h 45mUnited Airlines
Deal found 10/14$490
This American Airlines deal was found by Cheapflights users on 10/13. 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.
Mon 11/1011:48 amORD - GRU
1 stop15h 17mAmerican Airlines
Sun 11/2310:35 pmGRU - ORD
1 stop15h 16mAmerican Airlines
Deal found 10/13$493

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Sao Paulo 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 October 14, 2025.
Use the filters below to find and compare flights from Chicago to Sao Paulo that are best for you.

Fly from

Chicago

Fly to

Sao Paulo

Route

Depart

Return

Price

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Wed 11/12

5:50 pm-7:15 am

Nonstop10h 25m

Sao Paulo Guarulhos Intl

Wed 11/19

9:45 pm-5:30 am

Nonstop10h 45m

$483

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Sun 11/9

1:35 pm-4:15 pm

1 stop23h 40m

Sao Paulo Guarulhos Intl

Tue 11/18

5:25 pm-12:15 pm

1 stop21h 50m

$486

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Wed 10/29

2:35 pm-4:15 pm

1 stop23h 40m

Sao Paulo Guarulhos Intl

Tue 11/11

5:25 pm-12:15 pm

1 stop21h 50m

$486

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Sun 11/9

8:50 am-10:20 am

1 stop22h 30m

Sao Paulo Guarulhos Intl

Tue 11/18

9:45 pm-5:30 am

Nonstop10h 45m

$490

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

Wed 11/12

6:48 am-7:20 pm

2 stops33h 32m

Sao Paulo Congonhas

Sat 11/22

6:05 am-11:06 pm

2 stops20h 01m

$567

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

Sat 11/8

7:34 pm-12:25 pm

3 stops37h 51m

Sao Paulo Congonhas

Tue 11/18

3:15 pm-11:06 pm

2 stops34h 51m

$570

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Fri 4/10

2:50 pm-4:05 pm

2 stops23h 15m

Sao Paulo Guarulhos Intl

Sat 4/18

4:50 pm-1:15 pm

1 stop22h 25m

$586

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 11/9

12:47 pm-9:35 am

1 stop17h 48m

Sao Paulo Guarulhos Intl

Tue 11/18

9:15 pm-11:52 am

1 stop17h 37m

$600

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Sun 11/9

6:45 am-5:40 am

2 stops19h 55m

Sao Paulo Guarulhos Intl

Sun 11/16

9:15 pm-4:46 pm

1 stop22h 31m

$605

ChicagoSao Paulo

ORD - VCP

ORDVCP

Chicago O'Hare Intl

Thu 11/6

12:17 pm-10:45 am

2 stops19h 28m

Sao Paulo Viracopos

Thu 11/13

1:00 pm-2:31 pm

2 stops28h 31m

$610

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 60 results
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Compare providers for flights from Chicago to Sao Paulo

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 Sao Paulo in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy2 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust 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-Sao Paulo flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Sao Paulo flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Sao Paulo flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Sao Paulo 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-Sao Paulo 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 Sao Paulo

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Sao Paulo. Price data was last updated on October 10, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Sao Paulo, you should look to book at least 10 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 Chicago to Sao Paulo?

Currently, May is the cheapest month in which you can book a flight from Chicago to Sao Paulo (average of $376). Flying from Chicago to Sao Paulo in August is currently the most expensive (average of $694). 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 SAO?

Find hourly flight availability from Chicago to Sao Paulo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 14, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 27% on flights from Chicago to Sao Paulo by exploring options for tickets in the morning.

What is the cheapest day to fly from Chicago to Sao Paulo?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Sao Paulo. Price data was last updated on December 1, 2024.

Travelers seeking maximum savings on their Chicago to Sao Paulo flight should consider departing on Monday afternoons when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Sao Paulo

Explore weekly flight availability from Chicago to Sao Paulo. 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 October 14, 2025.

The most flights from CHI to SAO are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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

What’s the top layover airport for flights from Chicago to Sao Paulo?

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

Panama City (PTY) – chosen by Cheapflights users on 92% of 1-stop itineraries from Chicago to Sao Paulo on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Sao Paulo?

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

Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of $672.

What’s the fastest layover option from Chicago to Sao Paulo?

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

Flights via Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 12h 55m.

Which airport typically offers the quickest layover for flights from Chicago to Sao Paulo?

Average layover duration for 1-stop one-way flights from Chicago to Sao Paulo, 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 06m.

Reviews of airlines servicing Sao Paulo

Get insights into the airlines that provide service to Sao Paulo. 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 Sao Paulo. Reviews last updated October 14, 2025.
Read reviews from past customers who have flown Copa Airlines, LATAM Airlines, and United Airlines from Chicago to Sao Paulo. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.6
Good
1,549 reviews

Comfort

7.4

Boarding

7.8

Crew

8.1

Overall

7.6

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Copa Airlines
7.6
Good
1,549 reviews
Copa Airlines
7.6
Good
1,549 reviews

Comfort

7.4

Boarding

7.8

Crew

8.1

Overall

7.6

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
LATAM Airlines
7.5
Good
1,866 reviews
Copa Airlines
7.6
Good
1,549 reviews

Comfort

7.4

Boarding

7.8

Crew

8.1

Overall

7.6

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
United Airlines
7.4
Good
8,977 reviews
Copa Airlines
7.6
Good
1,549 reviews

Comfort

7.4

Boarding

7.8

Crew

8.1

Overall

7.6

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Air Canada
7.1
Good
10,298 reviews
Copa Airlines
7.6
Good
1,549 reviews

Comfort

7.4

Boarding

7.8

Crew

8.1

Overall

7.6

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Avianca
6.6
Okay
2,450 reviews
Copa Airlines
7.6
Good
1,549 reviews

Comfort

7.4

Boarding

7.8

Crew

8.1

Overall

7.6

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip

Related info for your journey

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

  • How long is the flight from Chicago to Sao Paulo?

    For as low as $483, United Airlines can have you in Sao Paulo from Chicago in 10h 25m. The distance between Chicago and Sao Paulo is about 5233 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Sao Paulo round-trip?

    According to our current data, Copa Airlines ($376), United Airlines ($435), and Delta ($487) offers the cheapest pricing from Chicago to Sao Paulo. Copa Airlines is priced at 53% lower than the current average price of a flight leaving 3 months from now.

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

    The cheapest airline one-way is Arajet, with whom users have recently found tickets for as low as $203. However, be on the lookout for offers from GOL and Avianca, as they are both options that can get you from Chicago to Sao Paulo for a low price.

  • What are the most popular routes from Chicago to Sao Paulo?

    When deciding which route to take from Chicago to Sao Paulo consider Chicago O'Hare Intl - Sao Paulo Guarulhos Intl, Chicago O'Hare Intl - Sao Paulo Viracopos or Chicago Midway - Sao Paulo Guarulhos Intl as they are the most popular.

  • What are the cheapest flights from Chicago to Sao Paulo?

    While on average a flight from Chicago to Sao Paulo is generally $670, our data shows the cheapest flight currently is $303. When looking at the most popular route, (Chicago O'Hare Intl - Sao Paulo Guarulhos Intl), you can expect to pay $425 for that flight.

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

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

  • How can I find direct flights from Chicago to Sao Paulo?

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

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

    Yes. Cheapflights offers flight deals from Chicago to Sao Paulo 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 Sao Paulo?

    Currently, May is the cheapest month in which you can book a flight from Chicago to Sao Paulo (average of $376). Flying from Chicago to Sao Paulo in August is currently the most expensive (average of $694). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 7 airlines flying from Chicago to Sao Paulo

Discover the top 7 airlines that operate flights from Chicago to Sao Paulo. 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$376Average$690FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$435Average$1,003FlexibilityNo cancel feeOn-time69%
DeltaCheapest$487Average$667FlexibilityNo cancel feeOn-timeN/A
LATAM AirlinesCheapest$494Average$643FlexibilityNo cancel feeOn-time81%
American AirlinesCheapest$500Average$1,058FlexibilityNo cancel feeOn-time71%
AviancaCheapest$605Average$815FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$696Average$836FlexibilityNo cancel feeOn-time67%

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