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$202+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAO
Jan 26 — Feb 21
Mon 1/26
Mon 2/2
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Sao Paulo are usually found in January or February, booked 49 days in advance, depart on a Thursday or Monday and return on a Sunday

Cheap 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 December 27, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/277:33 amORD - GRU
1 stop13h 37mCopa Airlines
Sun 12/281:30 amGRU - ORD
1 stop14h 22mCopa Airlines
Deal found 12/25$816
This Trip.com deal was found by Cheapflights users on 12/26. 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.
Mon 12/295:45 amORD - GRU
1 stop13h 35mMultiple Airlines
Wed 12/317:35 amGRU - ORD
1 stop15h 45mMultiple Airlines
Deal found 12/26$875
This Air Canada deal was found by Cheapflights users on 12/26. 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 12/292:00 pmORD - GRU
2 stops16h 00mAir Canada
Wed 12/319:45 pmGRU - ORD
2 stops20h 25mAir Canada
Deal found 12/26$1,172
This Avianca deal was found by Cheapflights users on 12/25. 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.
Fri 12/2610:20 pmORD - GRU
1 stop14h 55mAvianca
Mon 1/52:40 amGRU - ORD
1 stop20h 40mAvianca
Deal found 12/25$1,360
This Mytrip deal was found by Cheapflights users on 12/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2912:09 pmORD - VCP
1 stop15h 26mMultiple Airlines
Wed 12/311:00 pmVCP - ORD
2 stops25h 14mMultiple Airlines
Deal found 12/25$1,392
This KAYAK deal was found by Cheapflights users on 12/25. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2712:39 pmORD - GRU
2 stops19h 41mLATAM Airlines
Mon 12/297:35 amGRU - ORD
2 stops19h 27mLATAM Airlines
Deal found 12/25$1,420
This FlightHub deal was found by Cheapflights users on 12/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/274:25 pmMDW - GRU
2 stops20h 45mLATAM Airlines
Mon 12/2910:40 amGRU - MDW
1 stop14h 42mLATAM Airlines
Deal found 12/25$1,472
This CheapOair deal was found by Cheapflights users on 12/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2710:20 pmORD - GRU
1 stop21h 20mAvianca
Fri 1/25:25 pmGRU - ORD
1 stop29h 55mAvianca
Deal found 12/25$1,495
This KAYAK deal was found by Cheapflights users on 12/26. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:05 pmMDW - GRU
2 stops16h 35mLATAM Airlines
Tue 12/303:55 amGRU - MDW
2 stops21h 27mLATAM Airlines
Deal found 12/26$1,548
This Kiwi.com deal was found by Cheapflights users on 12/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/293:10 pmMDW - GRU
1 stop14h 40mMultiple Airlines
Wed 12/3111:59 pmGRU - MDW
2 stops20h 39mMultiple Airlines
Deal found 12/25$1,686
This Expedia deal was found by Cheapflights users on 12/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/293:04 pmORD - CGH
2 stops16h 56mMultiple Airlines
Wed 12/316:10 pmCGH - ORD
2 stops28h 35mMultiple Airlines
Deal found 12/25$1,732
This Cheapflightsfares deal was found by Cheapflights users on 12/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:00 amMDW - GRU
2 stops20h 45mLATAM Airlines
Tue 1/68:15 amGRU - MDW
2 stops29h 12mLATAM Airlines
Deal found 12/25$2,203

Find 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 December 27, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$538
(Kiwi.com)

One-way from

$202
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$1,121

Good round-trip deal

$837 or less

Good one-way deal

$2,413 or less
Provider with most accurate pricing for Chicago (CHI)-Sao Paulo (SAO) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Sao Paulo (SAO) flights.
Search Deals
From Chicago (CHI) to Sao Paulo (SAO)
Search Deals
One-way flight from Chicago (CHI) to Sao Paulo (SAO)
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Sao Paulo (SAO).
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Sao Paulo (SAO).
Search Deals

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 December 27, 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 - CGH

ORDCGH

Chicago O'Hare Intl

Thu 3/5

7:10 am-4:30 pm

2 stops30h 20m

Sao Paulo Congonhas

Sun 3/8

2:40 pm-10:04 pm

2 stops33h 24m

$626

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Fri 5/15

7:20 pm-2:42 am

3 stops29h 22m

Sao Paulo Guarulhos Intl

Fri 5/22

1:45 am-1:15 pm

1 stop13h 30m

$691

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Sun 1/18

10:20 pm-10:40 pm

1 stop21h 20m

Sao Paulo Guarulhos Intl

Thu 1/22

2:40 am-8:20 pm

1 stop20h 40m

$706

ChicagoSao Paulo

ORD - VCP

ORDVCP

Chicago O'Hare Intl

Thu 3/5

2:12 pm-9:00 am

2 stops39h 48m

Sao Paulo Viracopos

Sun 3/8

10:10 am-11:38 pm

1 stop15h 28m

$750

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Fri 5/8

2:50 pm-1:00 pm

2 stops20h 10m

Sao Paulo Guarulhos Intl

Sun 5/24

7:20 am-1:15 pm

1 stop31h 55m

$756

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Sat 5/16

2:35 pm-2:10 am

1 stop33h 35m

Sao Paulo Guarulhos Intl

Sat 5/30

4:45 pm-9:25 pm

2 stops30h 40m

$764

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Thu 2/19

2:22 pm-6:30 am

1 stop13h 08m

Sao Paulo Guarulhos Intl

Tue 3/3

5:25 pm-9:39 am

2 stops19h 14m

$765

ChicagoSao Paulo

ORD - VCP

ORDVCP

Chicago O'Hare Intl

Mon 2/9

2:22 pm-7:40 pm

2 stops26h 18m

Sao Paulo Viracopos

Mon 2/16

11:20 pm-11:22 am

1 stop15h 02m

$777

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Sun 2/15

10:20 pm-1:35 am

1 stop24h 15m

Sao Paulo Guarulhos Intl

Thu 2/19

9:40 pm-9:24 pm

2 stops50h 44m

$791

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Fri 5/8

3:21 pm-6:30 am

1 stop13h 09m

Sao Paulo Guarulhos Intl

Sun 5/24

5:25 am-1:15 am

1 stop21h 50m

$800

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 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 December 19, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Sao Paulo, you should look to book at least 49 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 December 27, 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 16, 2024.

Travelers seeking maximum savings on their Chicago to Sao Paulo flight should consider departing on Monday mornings 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 December 27, 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 40% 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 evening 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 38% 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 December 27, 2025.
Read reviews from past customers who have flown Copa Airlines, United Airlines, and Air Canada 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
1,559 reviews

Overall

7.6

Crew

8.1

Entertainment

6.8

Food

6.8

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Copa Airlines
7.6
Good
1,559 reviews
Copa Airlines
7.6
Good
1,559 reviews

Overall

7.6

Crew

8.1

Entertainment

6.8

Food

6.8

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
United Airlines
7.4
Good
9,116 reviews
Copa Airlines
7.6
Good
1,559 reviews

Overall

7.6

Crew

8.1

Entertainment

6.8

Food

6.8

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Air Canada
7.1
Good
10,562 reviews
Copa Airlines
7.6
Good
1,559 reviews

Overall

7.6

Crew

8.1

Entertainment

6.8

Food

6.8

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Avianca
6.6
Okay
2,489 reviews
Copa Airlines
7.6
Good
1,559 reviews

Overall

7.6

Crew

8.1

Entertainment

6.8

Food

6.8

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.

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 $756, Air Canada can have you in Sao Paulo from Chicago in 20h 10m. 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 Avianca ($485) offers the cheapest pricing from Chicago to Sao Paulo. Copa Airlines is priced at 52% 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 Copa Airlines, with whom users have recently found tickets for as low as $219. However, be on the lookout for offers from Avianca and United Airlines, 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 Midway - Sao Paulo Guarulhos Intl or Chicago O'Hare Intl - Sao Paulo Viracopos 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 $1,692, our data shows the cheapest flight currently is $797. When looking at the most popular route, (Chicago O'Hare Intl - Sao Paulo Guarulhos Intl), you can expect to pay $446 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 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 December 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$376Average$676FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$435Average$983FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$500Average$1,058FlexibilityNo cancel feeOn-time71%
LATAM AirlinesCheapest$531Average$637FlexibilityNo cancel feeOn-time81%
AviancaCheapest$572Average$803FlexibilityNo cancel feeOn-time71%
GOLCheapest$596Average$610FlexibilityNo cancel feeOn-time74%
Air CanadaCheapest$615Average$823FlexibilityNo cancel feeOn-time67%

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