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$306+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
SAO — CHI
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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Cheapflights Tip: The best prices from Sao Paulo to Chicago are usually found in July or August, booked 24 days in advance, depart on a Monday or Tuesday and return on a Thursday

Cheap 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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$541
(Mytrip)

One-way from

$306
(Mytrip)

Popular in

January

Cheapest in

July

Average price

$895

Good round-trip deal

$708 or less

Good one-way deal

$348 or less
Provider with most accurate pricing for Sao Paulo (SAO)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Sao Paulo (SAO)-Chicago (CHI) flights.
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From Sao Paulo (SAO) to Chicago (CHI)
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One-way flight from Sao Paulo (SAO) to Chicago (CHI)
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Highest demand for flights based on searches. 12% potential increase in price ($130 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Sao Paulo (SAO) to Chicago (CHI).
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Price to beat on a one-way flight from Sao Paulo (SAO) to Chicago (CHI).
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Find 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 October 16, 2025.

This Mytrip deal was found by Cheapflights users on 10/13. 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.
Sat 11/11:20 amGRU - ORD
2 stops35h 27mMultiple Airlines
Sun 11/910:20 pmORD - GRU
1 stop21h 20mMultiple Airlines
Deal found 10/13$541
This Mytrip deal was found by Cheapflights users on 10/14. 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.
Wed 11/52:40 amGRU - ORD
3 stops24h 47mMultiple Airlines
Sat 11/810:20 pmORD - GRU
1 stop24h 15mMultiple Airlines
Deal found 10/14$559
This Mytrip deal was found by Cheapflights users on 10/13. 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.
Sun 11/211:20 pmVCP - ORD
1 stop14h 52mMultiple Airlines
Sun 11/96:48 amORD - VCP
1 stop22h 52mMultiple Airlines
Deal found 10/13$560
This Mytrip deal was found by Cheapflights users on 10/14. 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.
Thu 11/611:20 pmVCP - ORD
1 stop14h 52mMultiple Airlines
Sat 11/811:35 amORD - VCP
2 stops28h 45mMultiple Airlines
Deal found 10/14$562
This Air Canada deal was found by Cheapflights users on 10/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/219:45 pmGRU - ORD
1 stop20h 10mAir Canada
Mon 12/13:35 pmORD - GRU
1 stop14h 25mAir Canada
Deal found 10/13$575
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/179:15 pmGRU - ORD
2 stops28h 51mMultiple Airlines
Tue 12/22:07 pmORD - GRU
1 stop34h 43mMultiple Airlines
Deal found 10/14$576
This Air Canada deal was found by Cheapflights users on 10/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/219:45 pmGRU - ORD
1 stop16h 33mAir Canada
Sun 11/307:05 amORD - GRU
1 stop22h 55mAir Canada
Deal found 10/14$577
This Air Canada deal was found by Cheapflights users on 10/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/229:00 pmGRU - ORD
1 stop14h 51mAir Canada
Sun 10/267:15 amORD - GRU
1 stop23h 45mAir Canada
Deal found 10/14$581
This Air Canada deal was found by Cheapflights users on 10/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/189:30 pmGRU - ORD
2 stops20h 25mAir Canada
Tue 11/2512:50 pmORD - GRU
1 stop17h 10mAir Canada
Deal found 10/13$582
This Air Canada deal was found by Cheapflights users on 10/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/209:30 pmGRU - ORD
1 stop18h 31mAir Canada
Tue 11/2512:50 pmORD - GRU
1 stop17h 10mAir Canada
Deal found 10/14$584
This Mytrip deal was found by Cheapflights users on 10/14. 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.
Thu 11/66:05 amCGH - ORD
2 stops20h 01mMultiple Airlines
Sat 11/87:34 pmORD - CGH
3 stops37h 51mMultiple Airlines
Deal found 10/14$593
This Mytrip deal was found by Cheapflights users on 10/14. 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.
Mon 11/1711:20 pmVCP - ORD
2 stops22h 14mMultiple Airlines
Tue 12/212:32 pmORD - VCP
2 stops27h 43mMultiple Airlines
Deal found 10/14$632

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 October 16, 2025.
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

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Tue 4/14

11:10 am-11:40 pm

1 stop14h 30m

Chicago O'Hare Intl

Mon 4/27

4:30 am-10:25 pm

1 stop15h 55m

$577

Sao PauloChicago

CGH - ORD

CGHORD

Sao Paulo Congonhas

Thu 11/6

6:05 am-11:06 pm

2 stops20h 01m

Chicago O'Hare Intl

Sat 11/8

7:34 pm-12:25 pm

3 stops37h 51m

$593

Sao PauloChicago

CGH - ORD

CGHORD

Sao Paulo Congonhas

Tue 2/3

6:05 am-9:00 pm

3 stops41h 55m

Chicago O'Hare Intl

Tue 2/24

5:59 pm-1:25 pm

3 stops40h 26m

$642

Sao PauloChicago

CGH - ORD

CGHORD

Sao Paulo Congonhas

Thu 11/6

6:05 am-11:06 pm

2 stops20h 01m

Chicago O'Hare Intl

Wed 11/19

6:56 am-8:25 am

2 stops22h 29m

$651

Sao PauloChicago

VCP - ORD

VCPORD

Sao Paulo Viracopos

Sun 11/2

11:20 pm-6:34 pm

2 stops22h 14m

Chicago O'Hare Intl

Sun 11/9

5:10 am-7:00 pm

3 stops34h 50m

$727

Sao PauloChicago

VCP - ORD

VCPORD

Sao Paulo Viracopos

Sun 11/30

5:55 pm-10:35 am

2 stops43h 40m

Chicago O'Hare Intl

Sun 12/7

3:20 pm-7:15 pm

1 stop24h 55m

$730

Sao PauloChicago

CGH - ORD

CGHORD

Sao Paulo Congonhas

Tue 2/10

10:00 pm-6:10 pm

2 stops23h 10m

Chicago O'Hare Intl

Sun 2/15

5:50 pm-10:25 pm

2 stops25h 35m

$735

Sao PauloChicago

VCP - ORD

VCPORD

Sao Paulo Viracopos

Thu 12/11

10:00 am-9:19 pm

1 stop14h 19m

Chicago O'Hare Intl

Tue 12/30

1:34 pm-7:15 pm

2 stops26h 41m

$780

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Fri 10/31

3:10 am-1:05 am

1 stop23h 55m

Chicago O'Hare Intl

Thu 11/13

6:56 am-12:15 am

1 stop14h 19m

$782

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Sat 12/6

5:25 am-12:05 am

1 stop21h 40m

Chicago O'Hare Intl

Tue 1/20

7:35 am-12:15 am

1 stop13h 40m

$782

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice 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 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 October 10, 2025.

The best time to book flights from Sao Paulo to Chicago is 24 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, May is the cheapest month in which you can book a flight from Sao Paulo to Chicago (average of $408). Flying from Sao Paulo to Chicago in February 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 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 October 16, 2025.

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 October 16, 2025.

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).

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 October 16, 2025.
Get a feel of what it's like to fly with Copa Airlines and United Airlines 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
7.6
Good
1,549 reviews

Comfort

7.4

Overall

7.6

Boarding

7.8

Crew

8.1

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Copa Airlines
7.6
Good
1,549 reviews
Copa Airlines
7.6
Good
1,549 reviews

Comfort

7.4

Overall

7.6

Boarding

7.8

Crew

8.1

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
United Airlines
7.4
Good
8,979 reviews
Copa Airlines
7.6
Good
1,549 reviews

Comfort

7.4

Overall

7.6

Boarding

7.8

Crew

8.1

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip

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 14h 30m. Arajet provides one of the quickest options available for as low as $577. 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 $605, Avianca will fly you from Sao Paulo to Chicago and back. In addition to Avianca, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Copa Airlines and LATAM Airlines - these airlines can fly you to your destination from $609 and $643, respectively. You may be able to fly from Sao Paulo to Chicago for 31% less than the average price by searching for these airlines.

  • 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 $211. On average you can expect to pay $762. The most popular route, (Sao Paulo Guarulhos Intl - Chicago O'Hare Intl), can usually be booked for $546.

  • 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, May is the cheapest month in which you can book a flight from Sao Paulo to Chicago (average of $408). Flying from Sao Paulo to Chicago in February 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

Traveling to a place near Chicago?

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

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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 4 airlines flying from Sao Paulo to Chicago

Discover the top 4 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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
AviancaCheapest$605Average$730FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$609Average$760FlexibilityNo cancel feeOn-time70%
LATAM AirlinesCheapest$643Average$1,110FlexibilityNo cancel feeOn-time81%
United AirlinesCheapest$684Average$1,018FlexibilityNo cancel feeOn-time69%

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