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$298+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
SAO — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Sao Paulo to Chicago are usually found in September or March, booked 32 days in advance, depart on a Monday or Wednesday 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 June 12, 2025.

Round-trip from

$593
(Mytrip)

One-way from

$298
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$839

Good round-trip deal

$687 or less

Good one-way deal

$456 or less
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. 11% potential increase in price ($116 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/9. 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.
Tue 8/1210:55 pmVCP - ORD
1 stop23h 45mMultiple Airlines
Thu 9/41:03 pmORD - VCP
1 stop14h 32mMultiple Airlines
Deal found 6/9$593
This Flightnetwork deal was found by Cheapflights users on 6/11. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/161:50 amGRU - ORD
1 stop13h 25mMultiple Airlines
Sat 2/710:27 amORD - GRU
1 stop13h 15mMultiple Airlines
Deal found 6/11$617
This Avianca deal was found by Cheapflights users on 6/12. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/201:45 amGRU - ORD
1 stop13h 30mAvianca
Sat 9/202:35 pmORD - GRU
1 stop13h 00mAvianca
Deal found 6/12$630
This Copa Airlines deal was found by Cheapflights users on 6/12. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/13:10 amGRU - ORD
1 stop22h 42mCopa Airlines
Mon 8/187:54 amORD - GRU
1 stop14h 36mCopa Airlines
Deal found 6/12$634
This GOL deal was found by Cheapflights users on 6/10. 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 GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:00 amGRU - ORD
2 stops18h 26mGOL
Fri 10/32:50 pmORD - GRU
2 stops25h 50mGOL
Deal found 6/10$788
This GOL deal was found by Cheapflights users on 6/10. 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 GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/177:20 pmCGH - ORD
2 stops29h 04mGOL
Wed 2/45:00 amORD - CGH
2 stops22h 05mGOL
Deal found 6/10$798
This GOL deal was found by Cheapflights users on 6/11. 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 GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/45:55 pmVCP - ORD
2 stops31h 20mGOL
Sun 11/161:35 pmORD - VCP
2 stops18h 05mGOL
Deal found 6/11$838
This Air Canada deal was found by Cheapflights users on 6/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/79:40 pmGRU - ORD
1 stop23h 49mAir Canada
Tue 10/143:35 pmORD - GRU
1 stop16h 05mAir Canada
Deal found 6/12$850
This Booking.com deal was found by Cheapflights users on 6/10. 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 8/256:30 amCGH - ORD
2 stops18h 17mMultiple Airlines
Fri 8/295:05 amORD - CGH
3 stops27h 10mMultiple Airlines
Deal found 6/10$881
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
Tue 7/110:05 amGRU - MDW
1 stop13h 40mLATAM Airlines
Wed 10/110:35 amMDW - GRU
1 stop17h 05mLATAM Airlines
Deal found 6/10$892
This Mytrip deal was found by Cheapflights users on 6/11. 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 7/111:45 amGRU - MDW
3 stops33h 00mMultiple Airlines
Fri 7/1810:31 amMDW - GRU
3 stops44h 44mMultiple Airlines
Deal found 6/11$927
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/78:30 pmGRU - MDW
2 stops18h 02mDelta
Fri 10/171:00 pmMDW - GRU
2 stops18h 00mDelta
Deal found 6/12$981

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 June 12, 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

VCP - ORD

VCPORD

Sao Paulo Viracopos

Tue 8/12

10:55 pm-8:40 pm

1 stop23h 45m

Chicago O'Hare Intl

Thu 9/4

1:03 pm-5:35 am

1 stop14h 32m

$593

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Sun 11/16

1:50 am-12:15 pm

1 stop13h 25m

Chicago O'Hare Intl

Sat 2/7

10:27 am-2:42 am

1 stop13h 15m

$617

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Wed 8/20

1:45 am-1:15 pm

1 stop13h 30m

Chicago O'Hare Intl

Sat 9/20

2:35 pm-5:35 am

1 stop13h 00m

$630

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Fri 8/1

3:10 am-11:52 pm

1 stop22h 42m

Chicago O'Hare Intl

Mon 8/18

7:54 am-12:30 am

1 stop14h 36m

$634

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Thu 9/25

6:00 am-10:26 pm

2 stops18h 26m

Chicago O'Hare Intl

Fri 10/3

2:50 pm-6:40 pm

2 stops25h 50m

$788

Sao PauloChicago

CGH - ORD

CGHORD

Sao Paulo Congonhas

Mon 11/17

7:20 pm-9:24 pm

2 stops29h 04m

Chicago O'Hare Intl

Wed 2/4

5:00 am-6:05 am

2 stops22h 05m

$798

Sao PauloChicago

VCP - ORD

VCPORD

Sao Paulo Viracopos

Tue 11/4

5:55 pm-10:15 pm

2 stops31h 20m

Chicago O'Hare Intl

Sun 11/16

1:35 pm-10:40 am

2 stops18h 05m

$838

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Tue 10/7

9:40 pm-7:29 pm

1 stop23h 49m

Chicago O'Hare Intl

Tue 10/14

3:35 pm-9:40 am

1 stop16h 05m

$850

Sao PauloChicago

CGH - ORD

CGHORD

Sao Paulo Congonhas

Mon 8/25

6:30 am-10:47 pm

2 stops18h 17m

Chicago O'Hare Intl

Fri 8/29

5:05 am-10:15 am

3 stops27h 10m

$881

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 7/1

10:05 am-9:45 pm

1 stop13h 40m

Chicago Midway

Wed 10/1

10:35 am-5:40 am

1 stop17h 05m

$892

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 33 results
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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 June 9, 2025.

The best time to book flights from Sao Paulo to Chicago is 32 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, August is the cheapest month in which you can book a flight from Sao Paulo to Chicago (average of $245). Flying from Sao Paulo to Chicago in March is currently the most expensive (average of $321). 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 June 12, 2025.

When flying from Sao Paulo to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 13% versus a flight at noon.

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 June 12, 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).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Read reviews from past customers who have flown Azul, Delta and LATAM Airlines from Sao Paulo to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Azul
8.0
Very good
781 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.1

Boarding

8.1

Crew

8.6

Reviews

1 / 14
2.0
Mediocre

Mike,Feb 2025

NVT - LIS

Experience was terrible. Flight cancelled. Missed connection. Replace service with EuroAtlantic airlines. Awful seats, awful food.
Azul
8.0
Very good
781 reviews
Azul
8.0
Very good
781 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.1

Boarding

8.1

Crew

8.6

Reviews

1 / 14
2.0
Mediocre

Mike,Feb 2025

NVT - LIS

Experience was terrible. Flight cancelled. Missed connection. Replace service with EuroAtlantic airlines. Awful seats, awful food.
Delta
8.0
Very good
7,946 reviews
Azul
8.0
Very good
781 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.1

Boarding

8.1

Crew

8.6

Reviews

1 / 14
2.0
Mediocre

Mike,Feb 2025

NVT - LIS

Experience was terrible. Flight cancelled. Missed connection. Replace service with EuroAtlantic airlines. Awful seats, awful food.
LATAM Airlines
7.5
Good
1,785 reviews
Azul
8.0
Very good
781 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.1

Boarding

8.1

Crew

8.6

Reviews

1 / 14
2.0
Mediocre

Mike,Feb 2025

NVT - LIS

Experience was terrible. Flight cancelled. Missed connection. Replace service with EuroAtlantic airlines. Awful seats, awful food.
Copa Airlines
7.5
Good
1,451 reviews
Azul
8.0
Very good
781 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.1

Boarding

8.1

Crew

8.6

Reviews

1 / 14
2.0
Mediocre

Mike,Feb 2025

NVT - LIS

Experience was terrible. Flight cancelled. Missed connection. Replace service with EuroAtlantic airlines. Awful seats, awful food.
United Airlines
7.4
Good
8,790 reviews
Azul
8.0
Very good
781 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.1

Boarding

8.1

Crew

8.6

Reviews

1 / 14
2.0
Mediocre

Mike,Feb 2025

NVT - LIS

Experience was terrible. Flight cancelled. Missed connection. Replace service with EuroAtlantic airlines. Awful seats, awful food.

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.

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

    Currently priced at $630, 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 GOL - these airlines can fly you to your destination from $634 and $788, respectively. You may be able to fly from Sao Paulo to Chicago for 30% 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 Avianca, with whom users have recently found tickets for as low as $325. However, be on the lookout for offers from Copa Airlines and Arajet, 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 $742. The most popular route, (Sao Paulo Guarulhos Intl - Chicago O'Hare Intl), can usually be booked for $613.

  • 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, August is the cheapest month in which you can book a flight from Sao Paulo to Chicago (average of $245). Flying from Sao Paulo to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 5 airlines flying from Sao Paulo to Chicago

Discover the top 5 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
AviancaCheapest$606Average$770FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$609Average$885FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$687Average$1,186FlexibilityNo cancel feeOn-time69%
LATAM AirlinesCheapest$844Average$1,110FlexibilityNo cancel feeOn-time81%
Air CanadaCheapest$851Average$894FlexibilityNo cancel feeOn-time67%

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