HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Sao Paulo

$245+ 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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAO
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
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 August, 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 septiembre 11, 2025.

Round-trip from

$435
(United Airlines)

One-way from

$245
(Trip.com)

Popular in

December

Cheapest in

March

Average price

$1,097

Good round-trip deal

$844 or less

Good one-way deal

$345 or less
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. 9% potential increase in price ($96 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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

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 septiembre 11, 2025.

This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/209:15 pmORD - GRU
Nonstop10h 15mUnited Airlines
dom. 11/29:45 pmGRU - ORD
Nonstop10h 45mUnited Airlines
Deal found 9/11$435
This Copa Airlines deal was found by Cheapflights users on 9/10. 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.
mar. 9/168:02 amORD - GRU
1 stop17h 48mCopa Airlines
vie. 9/265:25 amGRU - ORD
1 stop20h 56mCopa Airlines
Deal found 9/10$438
This United Airlines deal was found by Cheapflights users on 9/10. 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.
lun. 10/68:00 amORD - GRU
1 stop23h 30mUnited Airlines
jue. 10/1610:20 pmGRU - ORD
Nonstop10h 25mUnited Airlines
Deal found 9/10$440
This United Airlines deal was found by Cheapflights users on 9/10. 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.
sáb. 11/89:08 pmORD - GRU
1 stop33h 22mUnited Airlines
dom. 11/1610:25 pmGRU - ORD
1 stop23h 05mUnited Airlines
Deal found 9/10$441
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/279:00 amORD - GRU
1 stop23h 20mUnited Airlines
lun. 11/1010:25 pmGRU - ORD
1 stop21h 28mUnited Airlines
Deal found 9/11$450
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/56:00 amORD - GRU
1 stop25h 30mUnited Airlines
mié. 10/1510:20 pmGRU - ORD
Nonstop10h 25mUnited Airlines
Deal found 9/11$452
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/259:00 pmORD - GRU
1 stop34h 30mUnited Airlines
mié. 11/59:45 pmGRU - ORD
Nonstop10h 45mUnited Airlines
Deal found 9/11$453
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/117:55 pmORD - GRU
1 stop33h 40mUnited Airlines
mar. 10/219:30 pmGRU - ORD
1 stop23h 50mUnited Airlines
Deal found 9/11$457
This Copa Airlines deal was found by Cheapflights users on 9/11. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/148:02 amORD - GRU
1 stop14h 08mCopa Airlines
lun. 9/153:10 amGRU - ORD
1 stop23h 11mCopa Airlines
Deal found 9/11$458
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
mié. 10/157:59 amORD - GRU
1 stop14h 31mCopa Airlines
mié. 10/225:25 amGRU - ORD
1 stop20h 56mCopa Airlines
Deal found 9/11$463
This Trip.com deal was found by Cheapflights users on 9/9. 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.
lun. 10/279:45 amMDW - GRU
2 stops28h 30mMultiple Airlines
sáb. 11/82:40 amGRU - MDW
2 stops24h 50mMultiple Airlines
Deal found 9/9$502
This Mytrip deal was found by Cheapflights users on 9/10. 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. 10/157:43 pmORD - VCP
1 stop20h 02mMultiple Airlines
mié. 10/2210:50 pmVCP - ORD
1 stop14h 00mMultiple Airlines
Deal found 9/10$562

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 septiembre 11, 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

lun. 10/27

6:50 pm-7:15 am

Nonstop10h 25m

Sao Paulo Guarulhos Intl

lun. 11/10

9:45 pm-5:30 am

Nonstop10h 45m

$435

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

sáb. 12/13

6:15 pm-10:20 am

1 stop13h 05m

Sao Paulo Guarulhos Intl

sáb. 1/10

9:45 pm-5:30 am

Nonstop10h 45m

$435

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

mié. 2/4

5:50 pm-7:15 am

Nonstop10h 25m

Sao Paulo Guarulhos Intl

mié. 2/18

9:45 pm-5:30 am

Nonstop10h 45m

$435

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

mar. 10/7

7:59 am-12:30 am

1 stop14h 31m

Sao Paulo Guarulhos Intl

mar. 11/18

5:25 am-12:05 am

1 stop21h 40m

$438

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

mar. 11/11

6:56 am-3:50 am

1 stop17h 54m

Sao Paulo Guarulhos Intl

mar. 11/18

1:30 am-12:46 pm

1 stop14h 16m

$438

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

mié. 10/1

7:59 am-12:30 am

1 stop14h 31m

Sao Paulo Guarulhos Intl

sáb. 11/1

5:25 am-1:05 am

1 stop21h 40m

$438

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

mié. 10/1

7:59 am-12:10 am

1 stop14h 11m

Sao Paulo Guarulhos Intl

jue. 10/16

11:10 am-12:21 am

1 stop15h 11m

$438

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

dom. 10/12

10:00 am-9:30 am

1 stop21h 30m

Sao Paulo Guarulhos Intl

mié. 10/22

10:20 pm-6:45 am

Nonstop10h 25m

$440

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

sáb. 11/8

9:08 pm-9:30 am

1 stop33h 22m

Sao Paulo Guarulhos Intl

dom. 11/16

9:45 pm-5:30 am

Nonstop10h 45m

$442

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

jue. 10/30

6:50 pm-7:15 am

Nonstop10h 25m

Sao Paulo Guarulhos Intl

dom. 11/16

10:25 pm-6:30 pm

1 stop23h 05m

$445

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 60 results
1
2
3
...
6

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 August 29, 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, September is the cheapest month in which you can book a flight from Chicago to Sao Paulo (average of $677). 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 septiembre 11, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 17% 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. Sunday afternoons 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 septiembre 11, 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).

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 93% of 1-stop itineraries from Chicago to Sao Paulo on Cheapflights.

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

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

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

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

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

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

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

Average layover duration for 1-stop one-way flights from Chicago to Sao Paulo, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Panama City (PTY) offer the fastest connection on this route, with an average layover time of 1h 06m.

Reviews of airlines servicing Sao Paulo

Get insights into the airlines that provide service to Sao Paulo. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Sao Paulo. Reviews last updated septiembre 11, 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
1,531 reviews

Crew

8.1

Boarding

7.8

Entertainment

6.8

Overall

7.6

Food

6.8

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

PEI - PTY

The attention to us was excellent. Help was provided with care.
Copa Airlines
7.6
Good
1,531 reviews
Copa Airlines
7.6
Good
1,531 reviews

Crew

8.1

Boarding

7.8

Entertainment

6.8

Overall

7.6

Food

6.8

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

PEI - PTY

The attention to us was excellent. Help was provided with care.
LATAM Airlines
7.5
Good
1,847 reviews
Copa Airlines
7.6
Good
1,531 reviews

Crew

8.1

Boarding

7.8

Entertainment

6.8

Overall

7.6

Food

6.8

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

PEI - PTY

The attention to us was excellent. Help was provided with care.
United Airlines
7.4
Good
8,937 reviews
Copa Airlines
7.6
Good
1,531 reviews

Crew

8.1

Boarding

7.8

Entertainment

6.8

Overall

7.6

Food

6.8

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

PEI - PTY

The attention to us was excellent. Help was provided with care.
Air Canada
7.1
Good
10,000 reviews
Copa Airlines
7.6
Good
1,531 reviews

Crew

8.1

Boarding

7.8

Entertainment

6.8

Overall

7.6

Food

6.8

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

PEI - PTY

The attention to us was excellent. Help was provided with care.
Avianca
6.7
Okay
2,436 reviews
Copa Airlines
7.6
Good
1,531 reviews

Crew

8.1

Boarding

7.8

Entertainment

6.8

Overall

7.6

Food

6.8

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

PEI - PTY

The attention to us was excellent. Help was provided with care.

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 $435, United Airlines can have you in Sao Paulo from Chicago in 10h 25m. The distance between Chicago and Sao Paulo is about 5233 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, Copa Airlines ($376), Azul ($450), and Delta ($487) offers the cheapest pricing from Chicago to Sao Paulo. Copa Airlines is priced at 58% 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 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 $782, 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 $435 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, September is the cheapest month in which you can book a flight from Chicago to Sao Paulo (average of $677). 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

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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$376Average$694FlexibilityNo cancel feeOn-time70%
AzulCheapest$450Average$1,716FlexibilityNo cancel feeOn-time82%
DeltaCheapest$487Average$667FlexibilityNo cancel feeOn-timeN/A
LATAM AirlinesCheapest$494Average$643FlexibilityNo cancel feeOn-time81%
AviancaCheapest$605Average$849FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$696Average$841FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$761Average$1,081FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$849Average$1,013FlexibilityNo cancel feeOn-time71%

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.