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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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAO
dic. 26 — ene. 21
vie. 12/26
vie. 1/2
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 Wednesday and return on a Sunday

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 noviembre 26, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$525
(Kiwi.com)

One-way from

$203
(Arajet)

Popular in

December

Cheapest in

January

Average price

$697

Good round-trip deal

$841 or less

Good one-way deal

$2,413 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, 2% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($29 potential savings vs. average RT price).
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Average for round-trip flights in November 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 noviembre 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/23. 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.
mar. 12/211:40 amORD - GRU
2 stops42h 35mMultiple Airlines
sáb. 12/64:10 amGRU - ORD
1 stop20h 00mMultiple Airlines
Deal found 11/23$610
This Kiwi.com deal was found by Cheapflights users on 11/23. 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.
mié. 12/35:45 amORD - GRU
1 stop13h 35mArajet
sáb. 12/64:10 amGRU - ORD
1 stop20h 00mArajet
Deal found 11/23$624
This Kiwi.com deal was found by Cheapflights users on 11/23. 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.
mié. 12/311:40 amORD - GRU
2 stops36h 00mMultiple Airlines
dom. 12/711:10 amGRU - ORD
1 stop15h 55mMultiple Airlines
Deal found 11/23$642
This Expedia deal was found by Cheapflights users on 11/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/15:45 amORD - GRU
1 stop13h 35mArajet
sáb. 12/64:10 amGRU - ORD
1 stop20h 00mArajet
Deal found 11/23$648
This Avianca deal was found by Cheapflights users on 11/24. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/210:20 pmORD - GRU
1 stop14h 55mAvianca
lun. 2/27:35 amGRU - ORD
1 stop15h 45mAvianca
Deal found 11/24$654
This Avianca deal was found by Cheapflights users on 11/25. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/410:20 pmORD - GRU
1 stop21h 20mAvianca
vie. 2/61:20 amGRU - ORD
1 stop22h 00mAvianca
Deal found 11/25$656
This FlightHub deal was found by Cheapflights users on 11/23. 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.
mar. 12/210:20 pmORD - GRU
2 stops45h 35mAvianca
dom. 12/77:35 amGRU - ORD
1 stop15h 45mAvianca
Deal found 11/23$679
This Mytrip deal was found by Cheapflights users on 11/23. 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.
mar. 12/233:26 pmORD - VCP
3 stops40h 19mMultiple Airlines
sáb. 2/2811:20 pmVCP - ORD
1 stop15h 07mMultiple Airlines
Deal found 11/23$683
This Air Canada deal was found by Cheapflights users on 11/23. 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.
jue. 11/2712:50 pmORD - GRU
1 stop17h 10mAir Canada
jue. 12/49:45 pmGRU - ORD
1 stop20h 10mAir Canada
Deal found 11/23$688
This Kiwi.com deal was found by Cheapflights users on 11/23. 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.
mié. 12/33:43 pmORD - VCP
1 stop24h 37mMultiple Airlines
dom. 12/77:40 pmVCP - ORD
2 stops31h 25mMultiple Airlines
Deal found 11/23$717
This Mytrip deal was found by Cheapflights users on 11/23. 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.
mar. 12/233:26 pmORD - CGH
3 stops40h 34mMultiple Airlines
sáb. 2/285:05 pmCGH - ORD
3 stops34h 13mMultiple Airlines
Deal found 11/23$760
This Mytrip deal was found by Cheapflights users on 11/23. 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.
mié. 11/264:40 pmORD - CGH
3 stops40h 45mMultiple Airlines
lun. 12/16:35 pmCGH - ORD
2 stops31h 31mMultiple Airlines
Deal found 11/23$867

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 noviembre 26, 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

mié. 2/18

1:35 pm-10:40 pm

1 stop30h 05m

Sao Paulo Guarulhos Intl

mié. 3/18

1:20 am-1:15 pm

1 stop13h 55m

$573

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

mar. 2/24

4:47 pm-4:30 pm

2 stops20h 43m

Sao Paulo Congonhas

vie. 3/6

6:10 pm-1:01 pm

2 stops21h 51m

$576

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

dom. 2/8

7:05 am-5:40 am

1 stop19h 35m

Sao Paulo Guarulhos Intl

mar. 2/17

9:00 pm-9:56 am

1 stop15h 56m

$600

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

mié. 2/4

9:55 am-5:40 am

1 stop16h 45m

Sao Paulo Guarulhos Intl

vie. 2/13

11:45 pm-2:10 pm

1 stop17h 25m

$600

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

mié. 2/4

7:05 am-5:40 am

1 stop19h 35m

Sao Paulo Guarulhos Intl

dom. 2/15

9:00 pm-9:56 am

1 stop15h 56m

$600

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

mié. 2/4

9:55 am-5:40 am

1 stop16h 45m

Sao Paulo Guarulhos Intl

sáb. 2/14

11:45 pm-1:34 pm

1 stop16h 49m

$600

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

dom. 2/8

2:50 pm-9:35 am

1 stop15h 45m

Sao Paulo Guarulhos Intl

lun. 2/16

9:15 pm-1:34 pm

1 stop19h 19m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mié. 2/4

6:00 am-5:40 am

1 stop20h 40m

Sao Paulo Guarulhos Intl

sáb. 2/14

11:45 pm-10:06 am

1 stop13h 21m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

dom. 2/8

10:48 am-5:40 am

1 stop15h 52m

Sao Paulo Guarulhos Intl

dom. 2/15

9:15 pm-9:56 am

1 stop15h 41m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mié. 2/4

10:46 am-5:40 am

1 stop15h 54m

Sao Paulo Guarulhos Intl

dom. 2/15

11:45 pm-11:59 am

1 stop15h 14m

$600

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 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 Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Chicago-Sao Paulo flight deals on Cheapflights vs. Mytrip >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 Mytrip the most. Mytrip 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 November 21, 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 noviembre 26, 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 noviembre 26, 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 89% 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 18m.

How often are flights from Chicago to Sao Paulo delayed?

About 38% of weekly flights between Chicago and Sao Paulo have experienced delays in the past year, with the average delay time being 169 minutes.

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

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the morning 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 Wednesday 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 Sao Paulo flights?

Over the last year, Atlas Air have had the lowest number of delays on this route, with just 29% of flights being delayed.

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 noviembre 26, 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
1,569 reviews

Crew

8.1

Entertainment

6.8

Overall

7.6

Food

6.8

Boarding

7.8

Comfort

7.4

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
1,569 reviews
Copa Airlines
7.6
Good
1,569 reviews

Crew

8.1

Entertainment

6.8

Overall

7.6

Food

6.8

Boarding

7.8

Comfort

7.4

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
1,886 reviews
Copa Airlines
7.6
Good
1,569 reviews

Crew

8.1

Entertainment

6.8

Overall

7.6

Food

6.8

Boarding

7.8

Comfort

7.4

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
9,047 reviews
Copa Airlines
7.6
Good
1,569 reviews

Crew

8.1

Entertainment

6.8

Overall

7.6

Food

6.8

Boarding

7.8

Comfort

7.4

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
10,481 reviews
Copa Airlines
7.6
Good
1,569 reviews

Crew

8.1

Entertainment

6.8

Overall

7.6

Food

6.8

Boarding

7.8

Comfort

7.4

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
2,477 reviews
Copa Airlines
7.6
Good
1,569 reviews

Crew

8.1

Entertainment

6.8

Overall

7.6

Food

6.8

Boarding

7.8

Comfort

7.4

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 $600, GOL can have you in Sao Paulo from Chicago in 19h 35m. 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 51% 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 LATAM Airlines and GOL, 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 $1,967, our data shows the cheapest flight currently is $677. When looking at the most popular route, (Chicago O'Hare Intl - Sao Paulo Guarulhos Intl), you can expect to pay $456 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

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Top 8 airlines flying from Chicago to Sao Paulo

Discover the top 8 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 noviembre 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$376Average$678FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$435Average$996FlexibilityNo cancel feeOn-time69%
DeltaCheapest$487Average$627FlexibilityNo cancel feeOn-timeN/A
LATAM AirlinesCheapest$494Average$621FlexibilityNo cancel feeOn-time81%
American AirlinesCheapest$500Average$893FlexibilityNo cancel feeOn-time71%
AviancaCheapest$572Average$805FlexibilityNo cancel feeOn-time71%
GOLCheapest$596Average$620FlexibilityNo cancel feeOn-time74%
Air CanadaCheapest$696Average$831FlexibilityNo cancel feeOn-time67%

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