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$240+ Cheap flights from Sao Paulo, Brazil (SAO) to Chicago (CHI)

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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
SAO — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Find cheap flights from Sao Paulo to Chicago 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”

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Cheapflights Tip: The best prices from Sao Paulo to Chicago are usually found in April or July, booked 13 days in advance, depart on a Sunday or Tuesday and return on a Monday

Cheap flight deals from Sao Paulo to Chicago

Cheapest flights from Sao Paulo to Chicago
Explore the most affordable flight options available from Sao Paulo to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Booking.com deal was found by Cheapflights users on 1/27. 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.
Wed 5/279:35 pm
GRU
-
ORD
2 stops48h 33m
Air Canada
Wed 6/37:25 am
ORD
-
GRU
2 stops24h 25m
Air Canada
Deal found 1/27$609
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/201:00 am
GRU
-
ORD
2 stops19h 15m
Multiple Airlines
Thu 5/2811:20 pm
ORD
-
GRU
1 stop21h 10m
Multiple Airlines
Deal found 1/28$610
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 4/201:00 am
GRU
-
ORD
2 stops19h 15m
Multiple Airlines
Wed 5/272:35 pm
ORD
-
GRU
1 stop22h 45m
Multiple Airlines
Deal found 1/27$611
This Avianca deal was found by Cheapflights users on 1/27. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/151:20 am
GRU
-
ORD
1 stop22h 00m
Avianca
Mon 2/2310:20 pm
ORD
-
GRU
1 stop14h 55m
Avianca
Deal found 1/27$612
This Avianca deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/127:35 am
GRU
-
ORD
1 stop15h 45m
Avianca
Sun 3/2211:20 pm
ORD
-
GRU
1 stop21h 20m
Avianca
Deal found 1/28$613
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/134:05 am
GRU
-
ORD
1 stop31h 52m
Multiple Airlines
Fri 3/206:16 pm
ORD
-
GRU
2 stops30h 54m
Multiple Airlines
Deal found 1/27$614
This Mytrip deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1911:20 pm
VCP
-
ORD
1 stop15h 02m
Multiple Airlines
Wed 3/48:16 pm
ORD
-
VCP
1 stop20h 04m
Multiple Airlines
Deal found 1/29$615
This FlightHub deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:35 pm
GRU
-
ORD
1 stop21h 52m
Air Canada
Mon 9/285:57 pm
ORD
-
GRU
1 stop13h 08m
Air Canada
Deal found 1/28$615
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2312:00 pm
GRU
-
ORD
1 stop13h 40m
Multiple Airlines
Tue 5/2611:20 pm
ORD
-
GRU
1 stop21h 10m
Multiple Airlines
Deal found 1/28$616
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/221:00 am
GRU
-
ORD
2 stops24h 59m
Multiple Airlines
Wed 5/2711:20 pm
ORD
-
GRU
1 stop14h 45m
Multiple Airlines
Deal found 1/28$617
This Mytrip deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/611:20 pm
VCP
-
ORD
2 stops21h 26m
Multiple Airlines
Sat 3/146:01 pm
ORD
-
VCP
2 stops33h 39m
Multiple Airlines
Deal found 1/28$618
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 4/2410:37 pm
GRU
-
ORD
2 stops21h 38m
Multiple Airlines
Tue 5/262:35 pm
ORD
-
GRU
1 stop13h 00m
Multiple Airlines
Deal found 1/27$618

Find flight deals from Sao Paulo to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Sao Paulo (SAO) to Chicago (CHI). 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$609
(Booking.com)

One-way from

$240
(Trip.com)

Popular in

January

Cheapest in

April

Average price

$911

Good round-trip deal

$652 or less

Good one-way deal

$413 or less
Provider with most accurate pricing for Sao Paulo (SAO)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Sao Paulo (SAO)-Chicago (CHI) flights.
Search Deals
From Sao Paulo (SAO) to Chicago (CHI)
Search Deals
One-way flight from Sao Paulo (SAO) to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Sao Paulo (SAO) to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Sao Paulo (SAO) to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Sao Paulo to Chicago 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 January 29, 2026.
Use the filters below to find and compare flights from Sao Paulo to Chicago that are best for you.

Fly from

Sao Paulo

Fly to

Chicago

Route

Depart

Return

Price

Sao PauloChicago

VCP - ORD

VCPORD

Sao Paulo Viracopos

Thu 2/19

11:20 pm-11:22 am

1 stop15h 02m

Chicago O'Hare Intl

Wed 3/4

8:16 pm-7:20 pm

1 stop20h 04m

$615

Sao PauloChicago

VCP - ORD

VCPORD

Sao Paulo Viracopos

Fri 3/6

11:20 pm-5:46 pm

2 stops21h 26m

Chicago O'Hare Intl

Sat 3/14

6:01 pm-5:40 am

2 stops33h 39m

$618

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Sun 3/29

7:20 am-1:15 pm

1 stop31h 55m

Chicago O'Hare Intl

Sun 4/19

2:35 pm-12:40 am

1 stop32h 05m

$633

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Wed 2/18

1:20 am-11:47 pm

3 stops25h 27m

Chicago O'Hare Intl

Wed 3/4

8:16 pm-5:40 am

3 stops30h 24m

$636

Sao PauloChicago

VCP - ORD

VCPORD

Sao Paulo Viracopos

Wed 3/18

10:10 am-11:21 am

2 stops27h 11m

Chicago O'Hare Intl

Wed 6/3

7:41 am-5:35 am

2 stops19h 54m

$643

Sao PauloChicago

VCP - ORD

VCPORD

Sao Paulo Viracopos

Fri 5/1

7:40 pm-1:15 pm

2 stops19h 35m

Chicago O'Hare Intl

Sat 5/16

1:27 pm-5:45 pm

1 stop26h 18m

$656

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Tue 2/10

5:25 pm-8:18 am

2 stops17h 53m

Chicago O'Hare Intl

Wed 2/25

7:23 pm-4:15 pm

2 stops17h 52m

$671

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Fri 3/13

10:15 pm-7:00 am

Nonstop10h 45m

Chicago O'Hare Intl

Tue 3/24

4:30 pm-7:50 am

1 stop13h 20m

$672

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Thu 3/12

10:15 pm-7:00 am

Nonstop10h 45m

Chicago O'Hare Intl

Mon 3/23

4:30 pm-7:50 am

1 stop13h 20m

$672

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Sun 3/15

10:15 pm-7:00 am

Nonstop10h 45m

Chicago O'Hare Intl

Sun 3/22

4:00 pm-9:30 am

1 stop15h 30m

$672

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

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

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 Sao Paulo to Chicago in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 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 Sao Paulo-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Sao Paulo-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Sao Paulo-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Sao Paulo-Chicago 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 Sao Paulo-Chicago 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 Sao Paulo to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Sao Paulo 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 Sao Paulo to Chicago

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

Use this chart to determine the optimal time to book a round-trip flight from Sao Paulo to Chicago. Price data was last updated on January 23, 2026.

The best time to book flights from Sao Paulo to Chicago is 13 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, December is the cheapest month in which you can book a flight from Sao Paulo to Chicago (average of $413). Flying from Sao Paulo to Chicago in February is currently the most expensive (average of $710). 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 SAO to CHI?

Find hourly flight availability from Sao Paulo to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

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

Weekly flight availability from Sao Paulo to Chicago

Explore weekly flight availability from Sao Paulo to Chicago. 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 January 29, 2026.

The most flights from SAO to CHI 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 Sao Paulo to Chicago?

How often are flights from Sao Paulo to Chicago delayed?

About 11% of weekly flights between Sao Paulo and Chicago have experienced delays in the past year, with the average delay time being 174 minutes.

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

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

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

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

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

Over the last year, United Airlines have had the lowest number of delays on this route, with just 11% of flights being delayed.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated January 29, 2026.
Get a feel of what it's like to fly with Copa Airlines, United Airlines, and Air Canada from Sao Paulo to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,560 reviews

Boarding

7.8

Comfort

7.4

Crew

8.1

Entertainment

6.8

Overall

7.5

Food

6.8

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
1,560 reviews
Copa Airlines
7.5
Good
1,560 reviews

Boarding

7.8

Comfort

7.4

Crew

8.1

Entertainment

6.8

Overall

7.5

Food

6.8

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
9,214 reviews
Copa Airlines
7.5
Good
1,560 reviews

Boarding

7.8

Comfort

7.4

Crew

8.1

Entertainment

6.8

Overall

7.5

Food

6.8

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
10,666 reviews
Copa Airlines
7.5
Good
1,560 reviews

Boarding

7.8

Comfort

7.4

Crew

8.1

Entertainment

6.8

Overall

7.5

Food

6.8

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
2,490 reviews
Copa Airlines
7.5
Good
1,560 reviews

Boarding

7.8

Comfort

7.4

Crew

8.1

Entertainment

6.8

Overall

7.5

Food

6.8

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 Sao Paulo to Chicago. 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 Sao Paulo to Chicago?

    A quick flight from Sao Paulo to Chicago can take about 10h 45m. GOL provides one of the quickest options available for as low as $672. The distance between Sao Paulo and Chicago is about 5233 mi. This flight may include one or multiple stops.

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

    Currently priced at $297, Copa Airlines will fly you from Sao Paulo to Chicago and back. In addition to Copa Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Avianca and United Airlines - these airlines can fly you to your destination from $605 and $684, respectively. You may be able to fly from Sao Paulo to Chicago for 64% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Sao Paulo to Chicago one-way?

    The cheapest airline one-way is Copa Airlines, with whom users have recently found tickets for as low as $315. However, be on the lookout for offers from Air Canada and United Airlines, as they are both options that can get you from Sao Paulo to Chicago for a low price.

  • What are the most popular routes from Sao Paulo to Chicago?

    When deciding which route to take from Sao Paulo to Chicago consider Sao Paulo Guarulhos Intl - Chicago O'Hare Intl, Sao Paulo Guarulhos Intl - Chicago Midway or Sao Paulo Viracopos - Chicago O'Hare Intl as they are the most popular.

  • What are the cheapest flights from Sao Paulo to Chicago?

    The cheapest flight price from Sao Paulo to Chicago is $297. On average you can expect to pay $1,389. The most popular route, (Sao Paulo Guarulhos Intl - Chicago O'Hare Intl), can usually be booked for $524.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Sao Paulo to Chicago 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 Sao Paulo to Chicago?

    Currently, December is the cheapest month in which you can book a flight from Sao Paulo to Chicago (average of $413). Flying from Sao Paulo to Chicago in February is currently the most expensive (average of $710). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Sao Paulo to Chicago

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

Top 3 airlines flying from Sao Paulo to Chicago

Discover the top 3 airlines that operate flights from Sao Paulo to Chicago. 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$297Average$760FlexibilityNo cancel feeOn-time70%
AviancaCheapest$605Average$783FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$684Average$864FlexibilityNo cancel feeOn-time69%

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