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Sao Paulo

$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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAO
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Find cheap flights from Chicago to Sao Paulo with Cheapflights

1. Tell us where you want to go

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2. Select your favorite providers

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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 Wednesday

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 November 13, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$428
(Copa Airlines)

One-way from

$203
(Arajet)

Popular in

December

Cheapest in

January

Average price

$716

Good round-trip deal

$905 or less

Good one-way deal

$303 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 ($32 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 November 13, 2025.

This Avianca deal was found by Cheapflights users on 11/12. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2610:20 pmORD - GRU
1 stop21h 20mAvianca
Sun 12/72:40 amGRU - ORD
1 stop20h 40mAvianca
Deal found 11/12$486
This Copa Airlines deal was found by Cheapflights users on 11/13. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:56 amORD - GRU
1 stop14h 19mCopa Airlines
Tue 12/23:10 amGRU - ORD
1 stop23h 55mCopa Airlines
Deal found 11/13$488
This FlightHub deal was found by Cheapflights users on 11/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/310:20 pmORD - GRU
1 stop21h 20mAvianca
Sun 12/141:20 amGRU - ORD
1 stop22h 00mAvianca
Deal found 11/12$513
This Avianca deal was found by Cheapflights users on 11/12. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/310:20 pmORD - GRU
1 stop28h 20mAvianca
Wed 12/102:40 amGRU - ORD
1 stop20h 40mAvianca
Deal found 11/12$526
This Priceline deal was found by Cheapflights users on 11/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/310:20 pmORD - GRU
1 stop21h 20mAvianca
Mon 12/151:20 amGRU - ORD
1 stop22h 00mAvianca
Deal found 11/12$536
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/35:45 amORD - GRU
1 stop13h 35mMultiple Airlines
Mon 12/85:25 amGRU - ORD
2 stops40h 11mMultiple Airlines
Deal found 11/11$538
This Mytrip deal was found by Cheapflights users on 11/12. 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 12/310:20 pmORD - GRU
1 stop21h 20mMultiple Airlines
Sun 12/147:35 amGRU - ORD
1 stop31h 40mMultiple Airlines
Deal found 11/12$556
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/35:45 amORD - GRU
1 stop13h 35mMultiple Airlines
Wed 12/1011:59 pmGRU - ORD
2 stops21h 37mMultiple Airlines
Deal found 11/11$561
This Copa Airlines deal was found by Cheapflights users on 11/12. 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.
Thu 12/42:07 pmORD - GRU
1 stop13h 23mCopa Airlines
Fri 2/61:40 amGRU - ORD
1 stop13h 51mCopa Airlines
Deal found 11/12$568
This Delta deal was found by Cheapflights users on 11/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2612:47 pmMDW - GRU
1 stop13h 53mDelta
Mon 12/89:15 pmGRU - MDW
1 stop15h 39mDelta
Deal found 11/12$600
This FlightHub deal was found by Cheapflights users on 11/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2710:47 amMDW - GRU
1 stop15h 53mLATAM Airlines
Wed 12/311:45 pmGRU - MDW
1 stop15h 10mLATAM Airlines
Deal found 11/12$601
This LATAM Airlines deal was found by Cheapflights users on 11/13. 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1910:47 amMDW - GRU
2 stops15h 58mLATAM Airlines
Sun 11/3011:45 pmGRU - MDW
1 stop15h 07mLATAM Airlines
Deal found 11/13$611

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 November 13, 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

Mon 3/2

7:34 am-12:15 am

1 stop13h 41m

Sao Paulo Guarulhos Intl

Thu 3/5

3:10 am-12:04 am

1 stop23h 54m

$476

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Fri 2/13

1:35 pm-4:15 pm

1 stop23h 40m

Sao Paulo Guarulhos Intl

Thu 2/19

1:20 am-12:15 pm

1 stop13h 55m

$486

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Mon 2/9

1:35 pm-4:15 pm

1 stop23h 40m

Sao Paulo Guarulhos Intl

Sun 2/22

7:35 am-12:15 pm

1 stop31h 40m

$486

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Thu 1/22

11:51 pm-8:50 pm

1 stop17h 59m

Sao Paulo Guarulhos Intl

Thu 1/29

5:25 am-12:24 am

1 stop21h 59m

$538

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Mon 2/9

8:45 am-3:25 am

3 stops39h 40m

Sao Paulo Guarulhos Intl

Sun 2/22

6:00 am-2:19 pm

2 stops35h 19m

$595

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 11/27

10:47 am-5:40 am

1 stop15h 53m

Sao Paulo Guarulhos Intl

Wed 12/3

9:15 pm-9:54 am

1 stop15h 39m

$600

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Thu 1/22

9:52 am-5:40 am

1 stop16h 48m

Sao Paulo Guarulhos Intl

Thu 1/29

7:35 am-11:57 pm

2 stops19h 22m

$601

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Wed 2/4

6:50 am-5:40 am

2 stops19h 50m

Sao Paulo Guarulhos Intl

Wed 2/18

11:45 pm-4:40 pm

2 stops19h 55m

$605

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Wed 11/26

8:55 am-5:40 am

2 stops17h 45m

Sao Paulo Guarulhos Intl

Mon 12/8

10:50 pm-12:43 pm

1 stop16h 53m

$605

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Thu 11/27

9:42 am-5:40 am

2 stops16h 58m

Sao Paulo Guarulhos Intl

Wed 12/3

9:15 pm-8:39 am

1 stop14h 24m

$605

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

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 7, 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 November 13, 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 November 13, 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.

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 November 13, 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
1,565 reviews

Comfort

7.4

Crew

8.1

Food

6.9

Boarding

7.8

Entertainment

6.8

Overall

7.6

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
1,565 reviews
Copa Airlines
7.6
Good
1,565 reviews

Comfort

7.4

Crew

8.1

Food

6.9

Boarding

7.8

Entertainment

6.8

Overall

7.6

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
1,875 reviews
Copa Airlines
7.6
Good
1,565 reviews

Comfort

7.4

Crew

8.1

Food

6.9

Boarding

7.8

Entertainment

6.8

Overall

7.6

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
9,016 reviews
Copa Airlines
7.6
Good
1,565 reviews

Comfort

7.4

Crew

8.1

Food

6.9

Boarding

7.8

Entertainment

6.8

Overall

7.6

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
10,444 reviews
Copa Airlines
7.6
Good
1,565 reviews

Comfort

7.4

Crew

8.1

Food

6.9

Boarding

7.8

Entertainment

6.8

Overall

7.6

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
2,475 reviews
Copa Airlines
7.6
Good
1,565 reviews

Comfort

7.4

Crew

8.1

Food

6.9

Boarding

7.8

Entertainment

6.8

Overall

7.6

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 $476, Copa Airlines can have you in Sao Paulo from Chicago in 13h 41m. 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 52% lower than the current average price of a flight leaving 3 months from now.

  • 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 $1,325, 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 $428 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$376Average$690FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$435Average$1,001FlexibilityNo cancel feeOn-time69%
DeltaCheapest$487Average$667FlexibilityNo cancel feeOn-timeN/A
LATAM AirlinesCheapest$494Average$636FlexibilityNo cancel feeOn-time81%
American AirlinesCheapest$500Average$1,058FlexibilityNo cancel feeOn-time71%
GOLCheapest$596Average$620FlexibilityNo cancel feeOn-time74%
AviancaCheapest$605Average$811FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$696Average$834FlexibilityNo cancel feeOn-time67%

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