HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Sao Paulo

$262+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAO
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
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 May, booked 10 days in advance, depart on a Thursday or Wednesday and return on a Monday

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 agosto 14, 2025.

Round-trip from

$475
(United Airlines)

One-way from

$262
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$773

Good round-trip deal

$794 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 ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 agosto 14, 2025.

This United Airlines deal was found by Cheapflights users on 8/14. 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.
mié. 9/179:15 pmORD - GRU
Nonstop10h 15mUnited Airlines
sáb. 9/2710:20 pmGRU - ORD
Nonstop10h 25mUnited Airlines
Deal found 8/14$475
This Copa Airlines deal was found by Cheapflights users on 8/14. 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.
mié. 9/178:02 amORD - GRU
1 stop17h 48mCopa Airlines
sáb. 9/275:25 amGRU - ORD
1 stop20h 56mCopa Airlines
Deal found 8/14$478
This United Airlines deal was found by Cheapflights users on 8/14. 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.
jue. 9/118:50 amORD - GRU
1 stop22h 40mUnited Airlines
dom. 9/219:50 pmGRU - ORD
1 stop14h 23mUnited Airlines
Deal found 8/14$490
This United Airlines deal was found by Cheapflights users on 8/14. 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. 9/159:15 pmORD - GRU
Nonstop10h 15mUnited Airlines
jue. 9/259:30 pmGRU - ORD
1 stop27h 45mUnited Airlines
Deal found 8/14$492
This United Airlines deal was found by Cheapflights users on 8/14. 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. 9/139:05 pmORD - GRU
1 stop32h 30mUnited Airlines
mar. 9/2310:20 pmGRU - ORD
Nonstop10h 25mUnited Airlines
Deal found 8/14$493
This United Airlines deal was found by Cheapflights users on 8/14. 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. 9/711:40 amORD - GRU
1 stop19h 50mUnited Airlines
mié. 9/179:30 pmGRU - ORD
1 stop27h 45mUnited Airlines
Deal found 8/14$497
This Copa Airlines deal was found by Cheapflights users on 8/14. 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. 9/218:02 amORD - GRU
1 stop17h 48mCopa Airlines
jue. 9/253:10 amGRU - ORD
1 stop23h 11mCopa Airlines
Deal found 8/14$498
This 123 Milhas deal was found by Cheapflights users on 8/14. 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 123 Milhas is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/238:02 amORD - GRU
1 stop14h 28mCopa Airlines
jue. 10/21:30 amGRU - ORD
1 stop24h 51mCopa Airlines
Deal found 8/14$534
This United Airlines deal was found by Cheapflights users on 8/14. 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. 10/69:15 pmORD - GRU
Nonstop10h 15mUnited Airlines
dom. 10/1910:20 pmGRU - ORD
Nonstop10h 25mUnited Airlines
Deal found 8/14$538
This United Airlines deal was found by Cheapflights users on 8/14. 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. 10/276:50 pmORD - GRU
Nonstop10h 25mUnited Airlines
dom. 11/910:25 pmGRU - ORD
1 stop16h 25mUnited Airlines
Deal found 8/14$548
This Mytrip deal was found by Cheapflights users on 8/14. 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. 10/226:00 amORD - VCP
1 stop21h 35mMultiple Airlines
vie. 10/2410:50 pmVCP - ORD
1 stop13h 57mMultiple Airlines
Deal found 8/14$549
This Trip.com deal was found by Cheapflights users on 8/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/810:27 amORD - CGH
2 stops21h 58mMultiple Airlines
lun. 9/156:30 amCGH - ORD
2 stops28h 48mMultiple Airlines
Deal found 8/12$560

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 agosto 14, 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

jue. 9/11

9:15 pm-9:30 am

Nonstop10h 15m

Sao Paulo Guarulhos Intl

dom. 9/21

10:20 pm-6:45 am

Nonstop10h 25m

$475

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

mié. 9/17

9:15 pm-9:30 am

Nonstop10h 15m

Sao Paulo Guarulhos Intl

sáb. 9/27

10:20 pm-6:45 am

Nonstop10h 25m

$475

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

dom. 9/7

9:15 pm-9:30 am

Nonstop10h 15m

Sao Paulo Guarulhos Intl

mié. 9/17

10:20 pm-6:45 am

Nonstop10h 25m

$475

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

vie. 9/5

9:15 pm-9:30 am

Nonstop10h 15m

Sao Paulo Guarulhos Intl

lun. 9/15

10:20 pm-6:45 am

Nonstop10h 25m

$475

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

mié. 9/17

3:07 pm-6:30 am

1 stop13h 23m

Sao Paulo Guarulhos Intl

vie. 9/26

3:10 am-12:21 am

1 stop23h 11m

$478

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

mar. 9/23

8:02 am-6:30 am

1 stop20h 28m

Sao Paulo Guarulhos Intl

vie. 10/3

11:10 am-12:21 am

1 stop15h 11m

$478

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

lun. 10/20

3:07 pm-6:30 am

1 stop13h 23m

Sao Paulo Guarulhos Intl

dom. 11/2

5:25 am-12:05 am

1 stop21h 40m

$478

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

mié. 10/1

7:53 am-3:50 am

1 stop17h 57m

Sao Paulo Guarulhos Intl

mar. 10/7

11:10 am-12:21 am

1 stop15h 11m

$478

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

lun. 11/10

6:56 am-12:15 am

1 stop14h 19m

Sao Paulo Guarulhos Intl

sáb. 11/22

3:10 am-12:05 am

1 stop23h 55m

$478

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

lun. 9/22

8:02 am-3:50 am

1 stop17h 48m

Sao Paulo Guarulhos Intl

vie. 9/26

11:10 am-12:21 am

1 stop15h 11m

$478

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

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 8, 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 $676). 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 agosto 14, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 19% 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 agosto 14, 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 92% 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 agosto 14, 2025.
Read reviews from past customers who have flown LATAM Airlines, Copa 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.
LATAM Airlines
7.5
Good
1,840 reviews

Crew

8.0

Comfort

7.4

Boarding

7.6

Overall

7.5

Entertainment

7.0

Food

6.7

Reviews

1 / 20
4.0
Okay

Murilo,Jun 2025

SFO - LAX

I had mixed feelings regarding this flight. Called several times Latam and Delta regarding the purchase of checked baggage and price. I was told 80 dollars, could not buy it ahead of time,, they told me it was not Possible, that I had to buy at the airport. Check in my luggage the attendant says 80 dollars but I was charged 200 . No one could get me a solid answer why. Very disappointing
LATAM Airlines
7.5
Good
1,840 reviews
LATAM Airlines
7.5
Good
1,840 reviews

Crew

8.0

Comfort

7.4

Boarding

7.6

Overall

7.5

Entertainment

7.0

Food

6.7

Reviews

1 / 20
4.0
Okay

Murilo,Jun 2025

SFO - LAX

I had mixed feelings regarding this flight. Called several times Latam and Delta regarding the purchase of checked baggage and price. I was told 80 dollars, could not buy it ahead of time,, they told me it was not Possible, that I had to buy at the airport. Check in my luggage the attendant says 80 dollars but I was charged 200 . No one could get me a solid answer why. Very disappointing
Copa Airlines
7.5
Good
1,509 reviews
LATAM Airlines
7.5
Good
1,840 reviews

Crew

8.0

Comfort

7.4

Boarding

7.6

Overall

7.5

Entertainment

7.0

Food

6.7

Reviews

1 / 20
4.0
Okay

Murilo,Jun 2025

SFO - LAX

I had mixed feelings regarding this flight. Called several times Latam and Delta regarding the purchase of checked baggage and price. I was told 80 dollars, could not buy it ahead of time,, they told me it was not Possible, that I had to buy at the airport. Check in my luggage the attendant says 80 dollars but I was charged 200 . No one could get me a solid answer why. Very disappointing
United Airlines
7.4
Good
8,916 reviews
LATAM Airlines
7.5
Good
1,840 reviews

Crew

8.0

Comfort

7.4

Boarding

7.6

Overall

7.5

Entertainment

7.0

Food

6.7

Reviews

1 / 20
4.0
Okay

Murilo,Jun 2025

SFO - LAX

I had mixed feelings regarding this flight. Called several times Latam and Delta regarding the purchase of checked baggage and price. I was told 80 dollars, could not buy it ahead of time,, they told me it was not Possible, that I had to buy at the airport. Check in my luggage the attendant says 80 dollars but I was charged 200 . No one could get me a solid answer why. Very disappointing
Air Canada
7.1
Good
9,949 reviews
LATAM Airlines
7.5
Good
1,840 reviews

Crew

8.0

Comfort

7.4

Boarding

7.6

Overall

7.5

Entertainment

7.0

Food

6.7

Reviews

1 / 20
4.0
Okay

Murilo,Jun 2025

SFO - LAX

I had mixed feelings regarding this flight. Called several times Latam and Delta regarding the purchase of checked baggage and price. I was told 80 dollars, could not buy it ahead of time,, they told me it was not Possible, that I had to buy at the airport. Check in my luggage the attendant says 80 dollars but I was charged 200 . No one could get me a solid answer why. Very disappointing
Avianca
6.7
Okay
2,401 reviews
LATAM Airlines
7.5
Good
1,840 reviews

Crew

8.0

Comfort

7.4

Boarding

7.6

Overall

7.5

Entertainment

7.0

Food

6.7

Reviews

1 / 20
4.0
Okay

Murilo,Jun 2025

SFO - LAX

I had mixed feelings regarding this flight. Called several times Latam and Delta regarding the purchase of checked baggage and price. I was told 80 dollars, could not buy it ahead of time,, they told me it was not Possible, that I had to buy at the airport. Check in my luggage the attendant says 80 dollars but I was charged 200 . No one could get me a solid answer why. Very disappointing

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, 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 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 $713, 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 $541 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 $676). 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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$376Average$693FlexibilityNo cancel feeOn-time70%
AzulCheapest$450Average$1,716FlexibilityNo cancel feeOn-time82%
DeltaCheapest$487Average$667FlexibilityNo cancel feeOn-timeN/A
LATAM AirlinesCheapest$494Average$648FlexibilityNo cancel feeOn-time81%
AviancaCheapest$605Average$856FlexibilityNo cancel feeOn-time71%
American AirlinesCheapest$727Average$988FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$748Average$862FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$773Average$1,091FlexibilityNo 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.