HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Sao Paulo

$267+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAO
may. 4 — may. 111
dom. 5/4
dom. 5/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Sao Paulo with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Sao Paulo are usually found in March or February, booked 55 days in advance, depart on a Thursday or Tuesday and return on a Tuesday

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 abril 29, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$495
(Trip.com)

One-way from

$267
(Trip.com)

Popular in

December

Cheapest in

March

Average price

$873

Good round-trip deal

$1,197 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. 1% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Sao Paulo (SAO).
Search Deals

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 abril 29, 2025.

This Trip.com deal was found by Cheapflights users on 4/29. 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.
dom. 5/259:17 amORD - GRU
2 stops37h 23mMultiple Airlines
mié. 6/44:10 amGRU - ORD
2 stops22h 26mMultiple Airlines
Deal found 4/29$495
This Priceline deal was found by Cheapflights users on 4/29. 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.
vie. 6/63:45 pmORD - GRU
3 stops21h 35mAvianca
lun. 6/164:50 pmGRU - ORD
1 stop22h 25mAvianca
Deal found 4/29$579
This Mytrip deal was found by Cheapflights users on 4/29. 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. 6/412:41 pmORD - VCP
1 stop14h 19mMultiple Airlines
sáb. 6/1410:15 amVCP - ORD
1 stop15h 30mMultiple Airlines
Deal found 4/29$627
This Gotogate deal was found by Cheapflights users on 4/29. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/133:07 pmORD - GRU
1 stop27h 43mCopa Airlines
vie. 6/205:25 amGRU - ORD
1 stop34h 22mCopa Airlines
Deal found 4/29$675
This GOL deal was found by Cheapflights users on 4/29. 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.
mar. 5/133:15 pmORD - GRU
2 stops37h 40mGOL
vie. 5/232:05 pmGRU - ORD
2 stops28h 00mGOL
Deal found 4/29$678
This Air Canada deal was found by Cheapflights users on 4/29. 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.
mié. 4/303:14 pmORD - GRU
1 stop16h 31mAir Canada
mié. 5/79:00 pmGRU - ORD
1 stop16h 32mAir Canada
Deal found 4/29$688
This Mytrip deal was found by Cheapflights users on 4/29. 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.
vie. 6/65:50 pmMDW - GRU
2 stops30h 25mMultiple Airlines
lun. 6/168:55 pmGRU - MDW
2 stops21h 29mMultiple Airlines
Deal found 4/29$703
This GOL deal was found by Cheapflights users on 4/29. 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.
mié. 9/35:00 amORD - CGH
2 stops23h 05mGOL
mar. 9/910:10 amCGH - ORD
2 stops32h 34mGOL
Deal found 4/29$723
This United Airlines deal was found by Cheapflights users on 4/29. 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.
dom. 5/259:20 pmORD - GRU
Nonstop10h 10mUnited Airlines
mié. 6/410:20 pmGRU - ORD
Nonstop10h 25mUnited Airlines
Deal found 4/29$754
This Mytrip deal was found by Cheapflights users on 4/28. 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.
jue. 6/125:15 amORD - CGH
2 stops31h 50mMultiple Airlines
jue. 6/196:05 amCGH - ORD
3 stops41h 51mMultiple Airlines
Deal found 4/28$796
This GOL deal was found by Cheapflights users on 4/29. 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.
jue. 8/212:32 pmORD - VCP
2 stops18h 08mGOL
lun. 8/259:45 amVCP - ORD
2 stops53h 30mGOL
Deal found 4/29$891
This KAYAK deal was found by Cheapflights users on 4/29. 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.
mar. 7/84:22 pmMDW - GRU
1 stop14h 38mLATAM Airlines
lun. 7/146:40 pmGRU - MDW
2 stops17h 01mLATAM Airlines
Deal found 4/29$905

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 abril 29, 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

dom. 5/25

9:17 am-12:40 am

2 stops37h 23m

Sao Paulo Guarulhos Intl

mié. 6/4

4:10 am-12:36 am

2 stops22h 26m

$495

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

vie. 6/6

3:45 pm-3:20 pm

3 stops21h 35m

Sao Paulo Guarulhos Intl

lun. 6/16

4:50 pm-1:15 pm

1 stop22h 25m

$579

ChicagoSao Paulo

ORD - VCP

ORDVCP

Chicago O'Hare Intl

mié. 6/4

12:41 pm-5:00 am

1 stop14h 19m

Sao Paulo Viracopos

sáb. 6/14

10:15 am-11:45 pm

1 stop15h 30m

$627

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

vie. 6/13

3:07 pm-8:50 pm

1 stop27h 43m

Sao Paulo Guarulhos Intl

vie. 6/20

5:25 am-1:47 pm

1 stop34h 22m

$675

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

mar. 5/13

3:15 pm-6:55 am

2 stops37h 40m

Sao Paulo Guarulhos Intl

vie. 5/23

2:05 pm-4:05 pm

2 stops28h 00m

$678

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

vie. 6/13

3:35 pm-9:45 am

1 stop16h 10m

Sao Paulo Guarulhos Intl

vie. 6/20

9:40 pm-12:54 pm

1 stop17h 14m

$687

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

vie. 6/6

5:50 pm-2:15 am

2 stops30h 25m

Sao Paulo Guarulhos Intl

lun. 6/16

8:55 pm-4:24 pm

2 stops21h 29m

$703

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

mié. 9/3

5:00 am-6:05 am

2 stops23h 05m

Sao Paulo Congonhas

mar. 9/9

10:10 am-4:44 pm

2 stops32h 34m

$723

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

dom. 5/25

9:20 pm-9:30 am

Nonstop10h 10m

Sao Paulo Guarulhos Intl

mié. 6/4

10:20 pm-6:45 am

Nonstop10h 25m

$754

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

jue. 6/12

5:15 am-3:05 pm

2 stops31h 50m

Sao Paulo Congonhas

jue. 6/19

6:05 am-9:56 pm

3 stops41h 51m

$796

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 36 results
1
2
3
4

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
MytripPrice 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago-Sao Paulo flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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 April 25, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Sao Paulo, you should look to book at least 55 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, April is the cheapest month in which you can book a flight from Chicago to Sao Paulo (average of $686). Flying from Chicago to Sao Paulo in December is currently the most expensive (average of $1,209). 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 abril 29, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 39% on flights from Chicago to Sao Paulo by exploring options for tickets at noon.

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 Sunday at noon when fares are most often at their lowest. Wednesday 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 abril 29, 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).

Rainfall in Sao Paulo by month

Plan your trip to Sao Paulo by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Sao Paulo ranges from 0.8 - 9.4 inches per month. January is typically the wettest month, when rainfall can reach 9.4 in. July is typically the driest time to visit Sao Paulo when rainfall is around 0.8 in.

Temperature in Sao Paulo by month

Plan your trip to Sao Paulo by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Sao Paulo, use this chart to help with planning. For those seeking warmer temperatures, January is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of June, when temperatures are typically at their lowest (around 62.6 F).

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 abril 29, 2025.
Get a feel of what it's like to fly with ANA, Azul and Delta from Chicago to Sao Paulo by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
ANA
8.3
Very good
852 reviews

Food

7.6

Entertainment

7.9

Boarding

8.5

Comfort

8.1

Crew

8.7

Overall

8.3

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
ANA
8.3
Very good
852 reviews
ANA
8.3
Very good
852 reviews

Food

7.6

Entertainment

7.9

Boarding

8.5

Comfort

8.1

Crew

8.7

Overall

8.3

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
Azul
8.0
Very good
777 reviews
ANA
8.3
Very good
852 reviews

Food

7.6

Entertainment

7.9

Boarding

8.5

Comfort

8.1

Crew

8.7

Overall

8.3

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
Delta
8.0
Very good
7,936 reviews
ANA
8.3
Very good
852 reviews

Food

7.6

Entertainment

7.9

Boarding

8.5

Comfort

8.1

Crew

8.7

Overall

8.3

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
LATAM Airlines
7.5
Good
1,767 reviews
ANA
8.3
Very good
852 reviews

Food

7.6

Entertainment

7.9

Boarding

8.5

Comfort

8.1

Crew

8.7

Overall

8.3

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
Copa Airlines
7.5
Good
1,411 reviews
ANA
8.3
Very good
852 reviews

Food

7.6

Entertainment

7.9

Boarding

8.5

Comfort

8.1

Crew

8.7

Overall

8.3

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.

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.

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

    According to our current data, Avianca ($579), Copa Airlines ($675), and GOL ($678) offers the cheapest pricing from Chicago to Sao Paulo. Avianca is priced at 42% 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 Avianca, with whom users have recently found tickets for as low as $271. However, be on the lookout for offers from GOL and Copa 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 O'Hare Intl - Sao Paulo Viracopos or Chicago O'Hare Intl - Sao Paulo Congonhas 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 $1,210, our data shows the cheapest flight currently is $1,033. When looking at the most popular route, (Chicago O'Hare Intl - Sao Paulo Guarulhos Intl), you can expect to pay $551 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, April is the cheapest month in which you can book a flight from Chicago to Sao Paulo (average of $686). Flying from Chicago to Sao Paulo in December is currently the most expensive (average of $1,209). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Santos

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 abril 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$376Average$746FlexibilityNo cancel feeOn-time70%
AzulCheapest$450Average$1,592FlexibilityNo cancel feeOn-time82%
DeltaCheapest$487Average$677FlexibilityNo cancel feeOn-timeN/A
LATAM AirlinesCheapest$494Average$648FlexibilityNo cancel feeOn-time81%
AviancaCheapest$605Average$873FlexibilityNo cancel feeOn-time71%
American AirlinesCheapest$727Average$988FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$758Average$1,246FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$773Average$1,208FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.