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Sao Paulo

$257+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAO
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago to Sao Paulo are usually found in January or March, booked 76 days in advance, depart on a Monday or Thursday and return on a Wednesday

Cheap flight deals from Chicago to Sao Paulo

Cheapest flights from Chicago to Sao Paulo
Explore the most affordable flight options available from Chicago to Sao Paulo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 27, 2026.

This Booking.com deal was found by Cheapflights users on 7/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:45 am
ORD
-
GRU
1 stop13h 45m
Arajet
Fri 9/1111:55 pm
GRU
-
ORD
1 stop13h 17m
Arajet
Deal found 7/23$518
This Trip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:45 am
ORD
-
GRU
1 stop13h 45m
Arajet
Sun 9/134:08 am
GRU
-
ORD
1 stop20h 02m
Arajet
Deal found 7/25$522
This Jetabroad deal was found by Cheapflights users on 7/24. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:45 am
ORD
-
GRU
1 stop13h 45m
Arajet
Fri 9/1811:55 pm
GRU
-
ORD
1 stop13h 17m
Arajet
Deal found 7/24$523
This Booking.com deal was found by Cheapflights users on 7/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:30 am
ORD
-
GRU
1 stop14h 55m
Arajet
Thu 10/2211:50 am
GRU
-
ORD
1 stop13h 50m
Arajet
Deal found 7/23$539
This CheapOair deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:12 pm
ORD
-
GRU
1 stop12h 56m
Arajet
Thu 9/2411:50 am
GRU
-
ORD
1 stop13h 50m
Arajet
Deal found 7/25$582
This Arajet deal was found by Cheapflights users on 7/22. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/264:30 am
ORD
-
GRU
1 stop25h 57m
Arajet
Fri 11/610:38 pm
GRU
-
ORD
1 stop13h 19m
Arajet
Deal found 7/22$585
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/249:10 pm
ORD
-
GRU
2 stops27h 40m
Multiple Airlines
Thu 10/2912:00 pm
GRU
-
ORD
1 stop13h 40m
Multiple Airlines
Deal found 7/23$589
This LATAM Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2310:54 am
MDW
-
GRU
2 stops16h 31m
LATAM Airlines
Mon 8/249:45 am
GRU
-
MDW
2 stops26h 14m
LATAM Airlines
Deal found 7/26$689
This CheapTickets deal was found by Cheapflights users on 7/24. 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 CheapTickets is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:05 am
ORD
-
VCP
1 stop31h 50m
Multiple Airlines
Tue 9/1510:40 pm
VCP
-
ORD
1 stop18h 40m
Multiple Airlines
Deal found 7/24$739
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:11 am
ORD
-
VCP
1 stop32h 44m
Multiple Airlines
Mon 9/2810:40 pm
VCP
-
ORD
1 stop18h 40m
Multiple Airlines
Deal found 7/25$741
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:11 am
ORD
-
VCP
1 stop32h 44m
Multiple Airlines
Wed 9/1610:40 pm
VCP
-
ORD
1 stop18h 05m
Multiple Airlines
Deal found 7/26$745
This FlightHub deal was found by Cheapflights users on 7/23. 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 11/185:25 pm
MDW
-
GRU
1 stop13h 10m
LATAM Airlines
Tue 11/2411:00 pm
GRU
-
MDW
2 stops39h 56m
LATAM Airlines
Deal found 7/23$747

Find flight deals from Chicago to Sao Paulo

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Sao Paulo (SAO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$518
(Booking.com)

One-way from

$257
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$961

Good round-trip deal

$963 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. 18% potential increase in price ($190 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 July 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Sao Paulo (SAO).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Sao Paulo that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 27, 2026.
Use the filters below to find and compare flights from Chicago to Sao Paulo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Thu 9/24

8:01 am-3:50 am

1 stop17h 49m

Sao Paulo Guarulhos Intl

Sun 9/27

11:10 am-1:02 am

1 stop15h 52m

$793

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Sat 8/22

8:02 am-6:30 am

1 stop20h 28m

Sao Paulo Guarulhos Intl

Fri 8/28

2:00 am-1:02 am

1 stop25h 02m

$793

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

Fri 8/21

3:10 pm-7:55 am

2 stops38h 45m

Sao Paulo Congonhas

Tue 8/25

6:00 am-11:30 pm

2 stops19h 30m

$1,009

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

Wed 10/7

4:33 pm-11:15 am

2 stops16h 42m

Sao Paulo Congonhas

Wed 10/21

8:10 pm-9:30 pm

2 stops27h 20m

$1,046

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

Thu 10/15

1:31 pm-6:50 pm

2 stops27h 19m

Sao Paulo Congonhas

Sat 10/31

6:05 am-11:33 pm

2 stops19h 28m

$1,058

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Tue 8/11

8:37 am-10:05 pm

2 stops35h 28m

Sao Paulo Guarulhos Intl

Tue 8/25

6:00 am-10:31 pm

2 stops18h 31m

$1,062

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

Tue 9/8

3:10 pm-11:15 am

2 stops18h 05m

Sao Paulo Congonhas

Tue 9/15

6:30 am-9:38 pm

2 stops17h 08m

$1,077

ChicagoSao Paulo

ORD - VCP

ORDVCP

Chicago O'Hare Intl

Fri 9/4

2:30 pm-10:40 am

2 stops18h 10m

Sao Paulo Viracopos

Sun 9/13

6:00 pm-9:38 pm

2 stops29h 38m

$1,119

ChicagoSao Paulo

ORD - VCP

ORDVCP

Chicago O'Hare Intl

Wed 10/14

2:51 pm-10:45 am

2 stops17h 54m

Sao Paulo Viracopos

Sun 10/18

6:00 pm-11:33 pm

2 stops31h 33m

$1,149

ChicagoSao Paulo

ORD - VCP

ORDVCP

Chicago O'Hare Intl

Fri 9/4

4:10 pm-10:40 am

2 stops16h 30m

Sao Paulo Viracopos

Fri 9/18

6:00 pm-11:30 pm

2 stops31h 30m

$1,149

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 60 resultsSorted by cheapest first
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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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
Kiwi.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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Sao Paulo flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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

What is the cheapest month to book a flight from Chicago to Sao Paulo?

Currently, March is the cheapest month in which you can book a flight from Chicago to Sao Paulo (average of $700). Flying from Chicago to Sao Paulo in December is currently the most expensive (average of $1,115). 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 July 27, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Sao Paulo as you normally would.

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 July 27, 2026.

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?

Airfare is below average for this route at the moment.
Chicago to Sao Paulo flights typically cost between $655 and $1,128 in September.
The cheapest round-trip price found within the last 5 days was $518 on Arajet (Sep 4-Sep 11).

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.

Punta Cana (PUJ) – chosen by Cheapflights users on 60% 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.

Panama City (PTY) is the most affordable 1-stop option, with an average round-trip price of $659.

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 Panama City (PTY) have the shortest average one-way travel time for 1-stop routes: 13h 16m.

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 12m.

How often are flights from Chicago to Sao Paulo delayed?

About 45% of weekly flights between Chicago and Sao Paulo have experienced delays in the past year, with the average delay time being 185 minutes.

What is the most punctual flight time for Chicago to Sao Paulo flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Wednesday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Sao Paulo flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 45% of flights being delayed.

How far ahead should I book a flight from Chicago to Sao Paulo?

To ensure you get the cheapest price possible for a flight from Chicago to Sao Paulo, you should look to book at least 9 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.

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 July 27, 2026.
Read reviews from past customers who have flown Copa Airlines,United Airlines, andAir Canada from Chicago to Sao Paulo. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.6
Good
1,561 reviews

Crew

8.1

Comfort

7.4

Food

6.9

Boarding

7.8

Overall

7.6

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jul 2026

BOS - PTY

Airline was delayed 1 hour, that made my layover flight be missed, gave wrong information about gates, they closed the gates in my face, rebooked me, and had business class, and rebooked me not business class
Copa Airlines
7.6
Good
1,561 reviews
Copa Airlines
7.6
Good
1,561 reviews

Crew

8.1

Comfort

7.4

Food

6.9

Boarding

7.8

Overall

7.6

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jul 2026

BOS - PTY

Airline was delayed 1 hour, that made my layover flight be missed, gave wrong information about gates, they closed the gates in my face, rebooked me, and had business class, and rebooked me not business class
United Airlines
7.4
Good
10,043 reviews
Copa Airlines
7.6
Good
1,561 reviews

Crew

8.1

Comfort

7.4

Food

6.9

Boarding

7.8

Overall

7.6

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jul 2026

BOS - PTY

Airline was delayed 1 hour, that made my layover flight be missed, gave wrong information about gates, they closed the gates in my face, rebooked me, and had business class, and rebooked me not business class
Air Canada
7.1
Good
11,394 reviews
Copa Airlines
7.6
Good
1,561 reviews

Crew

8.1

Comfort

7.4

Food

6.9

Boarding

7.8

Overall

7.6

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jul 2026

BOS - PTY

Airline was delayed 1 hour, that made my layover flight be missed, gave wrong information about gates, they closed the gates in my face, rebooked me, and had business class, and rebooked me not business class
Avianca
6.5
Okay
2,521 reviews
Copa Airlines
7.6
Good
1,561 reviews

Crew

8.1

Comfort

7.4

Food

6.9

Boarding

7.8

Overall

7.6

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jul 2026

BOS - PTY

Airline was delayed 1 hour, that made my layover flight be missed, gave wrong information about gates, they closed the gates in my face, rebooked me, and had business class, and rebooked me not business class

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 $1,238, Copa Airlines can have you in Sao Paulo from Chicago in 14h 40m. The distance between Chicago and Sao Paulo is about 5218 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, Arajet ($272), Copa Airlines ($359), and United Airlines ($435) offers the cheapest pricing from Chicago to Sao Paulo. Arajet is priced at 67% 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 Arajet, with whom users have recently found tickets for as low as $204. However, be on the lookout for offers from Avianca 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 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 $4,920, our data shows the cheapest flight currently is $841. When looking at the most popular route, (Chicago O'Hare Intl - Sao Paulo Guarulhos Intl), you can expect to pay $522 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, March is the cheapest month in which you can book a flight from Chicago to Sao Paulo (average of $700). Flying from Chicago to Sao Paulo in December is currently the most expensive (average of $1,115). 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 Sao Paulo?

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

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Alternative routes for Chicago to Sao Paulo

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Guarulhos Intl flights

Top 6 airlines flying from Chicago to Sao Paulo

Discover the top 6 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 July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
ArajetCheapest$272Average$533FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$359Average$683FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$435Average$1,018FlexibilityNo cancel feeOn-time69%
AviancaCheapest$485Average$719FlexibilityNo cancel feeOn-time71%
GOLCheapest$596Average$620FlexibilityNo cancel feeOn-time74%
Air CanadaCheapest$615Average$838FlexibilityNo cancel feeOn-time67%

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