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Sao Paulo

$232+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAO
Mar 25 — Apr 11
Wed 3/25
Wed 4/1
1 adult, Economy
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Find cheap flights from Chicago to Sao Paulo with Cheapflights

1. Tell us where you want to go

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

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Cheapflights Tip: The best prices from Chicago to Sao Paulo are usually found in January or March, booked 3 days in advance, depart on a Thursday or Monday and return on a Sunday

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 February 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/178:34 am
ORD
-
GRU
1 stop13h 36m
Multiple Airlines
Tue 3/3111:10 am
GRU
-
ORD
2 stops39h 12m
Multiple Airlines
Deal found 2/22$556
This Mytrip deal was found by Cheapflights users on 2/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/166:45 am
ORD
-
GRU
1 stop13h 35m
Multiple Airlines
Wed 4/15:15 pm
GRU
-
ORD
1 stop30h 05m
Multiple Airlines
Deal found 2/23$557
This Copa Airlines deal was found by Cheapflights users on 2/20. 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.
Mon 4/68:06 am
ORD
-
GRU
1 stop14h 04m
Copa Airlines
Mon 4/1311:10 am
GRU
-
ORD
1 stop16h 03m
Copa Airlines
Deal found 2/20$561
This Trip.com deal was found by Cheapflights users on 2/19. 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.
Thu 3/510:20 pm
ORD
-
GRU
1 stop21h 20m
Avianca
Tue 3/105:25 pm
GRU
-
ORD
1 stop29h 55m
Avianca
Deal found 2/19$563
This Trip.com deal was found by Cheapflights users on 2/21. 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.
Mon 3/96:45 am
ORD
-
GRU
1 stop13h 35m
Multiple Airlines
Mon 3/305:15 pm
GRU
-
ORD
1 stop30h 05m
Multiple Airlines
Deal found 2/21$566
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Thu 3/57:34 am
ORD
-
GRU
1 stop19h 56m
Copa Airlines
Mon 3/95:25 am
GRU
-
ORD
1 stop21h 39m
Copa Airlines
Deal found 2/19$567
This Justfly.com deal was found by Cheapflights users on 2/19. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/510:20 pm
ORD
-
GRU
1 stop24h 15m
Avianca
Wed 3/115:25 pm
GRU
-
ORD
1 stop29h 55m
Avianca
Deal found 2/19$568
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Fri 3/67:34 am
ORD
-
GRU
1 stop13h 36m
Copa Airlines
Tue 3/101:40 am
GRU
-
ORD
1 stop13h 51m
Copa Airlines
Deal found 2/19$570
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:20 pm
ORD
-
GRU
1 stop23h 50m
Avianca
Fri 5/292:20 am
GRU
-
ORD
1 stop21h 00m
Avianca
Deal found 2/19$574
This Mytrip deal was found by Cheapflights users on 2/21. 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.
Fri 4/1711:20 pm
ORD
-
GRU
1 stop21h 10m
Multiple Airlines
Mon 5/114:45 pm
GRU
-
ORD
2 stops32h 25m
Multiple Airlines
Deal found 2/21$575
This Travelocity deal was found by Cheapflights users on 2/20. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:45 am
ORD
-
GRU
1 stop13h 35m
Multiple Airlines
Sun 3/155:25 pm
GRU
-
ORD
1 stop29h 55m
Multiple Airlines
Deal found 2/20$576
This Mytrip deal was found by Cheapflights users on 2/21. 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.
Fri 4/173:31 pm
ORD
-
CGH
2 stops28h 54m
Multiple Airlines
Mon 5/111:30 pm
CGH
-
ORD
2 stops35h 40m
Multiple Airlines
Deal found 2/21$590

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 February 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$556
(Kiwi.com)

One-way from

$232
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$685

Good round-trip deal

$825 or less

Good one-way deal

$345 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
High demand for flights, 1% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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

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 February 23, 2026.
Use the filters below to find and compare flights from Chicago to Sao Paulo that are best for you.

Fly from

Chicago

Fly to

Sao Paulo

Route

Depart

Return

Price

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Mon 6/1

3:21 pm-6:30 am

1 stop13h 09m

Sao Paulo Guarulhos Intl

Fri 7/31

11:10 am-4:00 am

1 stop18h 50m

$621

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Mon 6/22

8:02 am-12:10 am

1 stop14h 08m

Sao Paulo Guarulhos Intl

Wed 7/8

11:10 am-4:00 am

1 stop18h 50m

$640

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Sat 6/20

8:02 am-3:50 am

1 stop17h 48m

Sao Paulo Guarulhos Intl

Mon 7/20

3:15 am-12:01 am

1 stop22h 46m

$640

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Sun 6/28

3:21 pm-6:30 am

1 stop13h 09m

Sao Paulo Guarulhos Intl

Sun 7/5

11:10 am-4:00 am

1 stop18h 50m

$641

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 5/11

12:51 pm-5:40 am

1 stop14h 49m

Sao Paulo Guarulhos Intl

Fri 5/22

10:50 pm-3:26 pm

1 stop18h 36m

$701

ChicagoSao Paulo

ORD - VCP

ORDVCP

Chicago O'Hare Intl

Wed 4/15

5:34 pm-5:45 pm

1 stop22h 11m

Sao Paulo Viracopos

Sat 4/18

8:30 am-2:20 pm

3 stops31h 50m

$714

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Tue 3/10

5:15 am-4:15 pm

3 stops33h 00m

Sao Paulo Guarulhos Intl

Wed 3/18

5:25 pm-8:25 am

2 stops17h 00m

$728

ChicagoSao Paulo

ORD - VCP

ORDVCP

Chicago O'Hare Intl

Tue 5/19

3:31 pm-11:00 am

2 stops17h 29m

Sao Paulo Viracopos

Wed 6/3

10:10 am-11:10 pm

1 stop15h 00m

$737

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

Fri 4/17

2:17 pm-10:25 pm

2 stops30h 08m

Sao Paulo Congonhas

Mon 5/11

6:30 am-10:57 pm

2 stops18h 27m

$747

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

Fri 8/21

2:32 pm-8:00 am

2 stops39h 28m

Sao Paulo Congonhas

Tue 8/25

6:30 am-10:31 pm

2 stops18h 01m

$756

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 60 results
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Compare providers for flights from Chicago to Sao Paulo

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Sao Paulo in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Sao Paulo flights, users find the pricing of 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

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 February 20, 2026.

To ensure you get the cheapest price possible for a flight from Chicago to Sao Paulo, you should look to book at least 3 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, May is the cheapest month in which you can book a flight from Chicago to Sao Paulo (average of $376). Flying from Chicago to Sao Paulo in August is currently the most expensive (average of $696). 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 February 23, 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 February 23, 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?

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 50% of 1-stop itineraries from Chicago to Sao Paulo on Cheapflights.

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

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

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

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

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

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

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

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

Flights via Panama City (PTY) offer the fastest connection on this route, with an average layover time of 1h 18m.

How often are flights from Chicago to Sao Paulo delayed?

About 41% of weekly flights between Chicago and Sao Paulo have experienced delays in the past year, with the average delay time being 182 minutes.

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

Historically, flights departing in the evening 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?

Thursday 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 41% of flights being delayed.

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 February 23, 2026.
Read reviews from past customers who have flown Copa Airlines, United Airlines, and Air 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
7.5
Good
1,556 reviews

Entertainment

6.8

Food

6.8

Crew

8.1

Overall

7.5

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Copa Airlines
7.5
Good
1,556 reviews
Copa Airlines
7.5
Good
1,556 reviews

Entertainment

6.8

Food

6.8

Crew

8.1

Overall

7.5

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
United Airlines
7.4
Good
9,344 reviews
Copa Airlines
7.5
Good
1,556 reviews

Entertainment

6.8

Food

6.8

Crew

8.1

Overall

7.5

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Air Canada
7.1
Good
10,742 reviews
Copa Airlines
7.5
Good
1,556 reviews

Entertainment

6.8

Food

6.8

Crew

8.1

Overall

7.5

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Avianca
6.6
Okay
2,498 reviews
Copa Airlines
7.5
Good
1,556 reviews

Entertainment

6.8

Food

6.8

Crew

8.1

Overall

7.5

Boarding

7.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.

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 $621, Copa Airlines can have you in Sao Paulo from Chicago in 13h 09m. 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 ($359), United Airlines ($435), and Avianca ($471) offers the cheapest pricing from Chicago to Sao Paulo. Copa Airlines is priced at 55% 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 Copa Airlines, with whom users have recently found tickets for as low as $219. However, be on the lookout for offers from Avianca and Air Canada, 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 $1,747, our data shows the cheapest flight currently is $314. When looking at the most popular route, (Chicago O'Hare Intl - Sao Paulo Guarulhos Intl), you can expect to pay $497 for that flight.

  • Can I find deals for flights from Chicago to Sao Paulo that include hotel bookings?

    Yes. In addition to deals on Chicago to Sao Paulo flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Sao Paulo?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Sao Paulo.

  • Can I find deals for business class flights from Chicago to Sao Paulo?

    Yes. Cheapflights offers flight deals from Chicago to Sao Paulo by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, May is the cheapest month in which you can book a flight from Chicago to Sao Paulo (average of $376). Flying from Chicago to Sao Paulo in August is currently the most expensive (average of $696). 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

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Top 7 airlines flying from Chicago to Sao Paulo

Discover the top 7 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 February 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$359Average$673FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$435Average$981FlexibilityNo cancel feeOn-time69%
AviancaCheapest$471Average$736FlexibilityNo cancel feeOn-time71%
American AirlinesCheapest$500Average$1,317FlexibilityNo cancel feeOn-time71%
LATAM AirlinesCheapest$531Average$607FlexibilityNo cancel feeOn-time81%
GOLCheapest$596Average$610FlexibilityNo cancel feeOn-time74%
Air CanadaCheapest$615Average$794FlexibilityNo cancel feeOn-time67%

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