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$281+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
SAO — CHI
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
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 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 August 13, 2025.

Round-trip from

$637
(Mytrip)

One-way from

$281
(Kiwi.com)

Popular in

January

Cheapest in

July

Average price

$786

Good round-trip deal

$834 or less

Good one-way deal

$284 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. 14% potential increase in price ($154 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 13, 2025.

This Mytrip deal was found by Cheapflights users on 8/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/251:45 amGRU - ORD
2 stops22h 13mMultiple Airlines
Fri 10/36:30 amORD - GRU
2 stops21h 05mMultiple Airlines
Deal found 8/12$637
This Mytrip deal was found by Cheapflights users on 8/11. 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.
Wed 9/246:30 amCGH - ORD
2 stops17h 28mMultiple Airlines
Sun 9/2810:27 amORD - CGH
3 stops20h 23mMultiple Airlines
Deal found 8/11$637
This Mytrip deal was found by Cheapflights users on 8/11. 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.
Sun 9/215:55 pmVCP - ORD
2 stops30h 03mMultiple Airlines
Thu 9/2510:27 amORD - VCP
3 stops28h 48mMultiple Airlines
Deal found 8/11$638
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/154:23 amGRU - ORD
2 stops30h 55mMultiple Airlines
Mon 9/2210:27 amORD - GRU
1 stop17h 13mMultiple Airlines
Deal found 8/11$639
This Mytrip deal was found by Cheapflights users on 8/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/101:45 amGRU - ORD
2 stops19h 05mMultiple Airlines
Mon 9/226:44 pmORD - GRU
3 stops42h 36mMultiple Airlines
Deal found 8/12$641
This Mytrip deal was found by Cheapflights users on 8/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1110:50 pmVCP - ORD
1 stop20h 49mMultiple Airlines
Mon 9/2210:27 amORD - VCP
3 stops28h 48mMultiple Airlines
Deal found 8/12$643
This Mytrip deal was found by Cheapflights users on 8/11. 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.
Sun 9/216:00 amGRU - ORD
2 stops17h 58mMultiple Airlines
Thu 9/2510:27 amORD - GRU
2 stops18h 33mMultiple Airlines
Deal found 8/11$643
This Mytrip deal was found by Cheapflights users on 8/11. 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.
Wed 9/241:45 amGRU - ORD
3 stops23h 03mMultiple Airlines
Thu 10/26:30 amORD - GRU
2 stops21h 05mMultiple Airlines
Deal found 8/11$645
This Mytrip deal was found by Cheapflights users on 8/11. 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.
Thu 9/257:40 pmVCP - ORD
3 stops28h 18mMultiple Airlines
Tue 9/3010:27 amORD - VCP
2 stops22h 13mMultiple Airlines
Deal found 8/11$646
This Mytrip deal was found by Cheapflights users on 8/11. 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.
Thu 9/256:30 amCGH - ORD
2 stops17h 28mMultiple Airlines
Tue 9/306:30 amORD - CGH
3 stops29h 35mMultiple Airlines
Deal found 8/11$647
This Mytrip deal was found by Cheapflights users on 8/11. 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.
Thu 9/1810:50 pmVCP - ORD
1 stop14h 02mMultiple Airlines
Sat 9/276:44 pmORD - VCP
1 stop21h 01mMultiple Airlines
Deal found 8/11$648
This Mytrip deal was found by Cheapflights users on 8/11. 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.
Sun 9/217:45 pmCGH - ORD
2 stops28h 13mMultiple Airlines
Thu 9/2510:27 amORD - CGH
3 stops22h 43mMultiple Airlines
Deal found 8/11$648

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 August 13, 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

Thu 9/25

1:45 am-9:58 pm

2 stops22h 13m

Chicago O'Hare Intl

Fri 10/3

6:30 am-5:35 am

2 stops21h 05m

$637

Sao PauloChicago

CGH - ORD

CGHORD

Sao Paulo Congonhas

Wed 9/24

6:30 am-9:58 pm

2 stops17h 28m

Chicago O'Hare Intl

Sun 9/28

10:27 am-8:50 am

3 stops20h 23m

$637

Sao PauloChicago

VCP - ORD

VCPORD

Sao Paulo Viracopos

Sun 9/21

5:55 pm-9:58 pm

2 stops30h 03m

Chicago O'Hare Intl

Thu 9/25

10:27 am-5:15 pm

3 stops28h 48m

$638

Sao PauloChicago

CGH - ORD

CGHORD

Sao Paulo Congonhas

Sun 10/5

9:00 pm-9:58 pm

3 stops26h 58m

Chicago O'Hare Intl

Sun 10/26

10:23 am-10:55 am

3 stops22h 32m

$642

Sao PauloChicago

VCP - ORD

VCPORD

Sao Paulo Viracopos

Thu 9/18

10:50 pm-10:52 am

1 stop14h 02m

Chicago O'Hare Intl

Sat 9/27

10:27 am-10:45 am

2 stops22h 18m

$643

Sao PauloChicago

VCP - ORD

VCPORD

Sao Paulo Viracopos

Thu 9/11

10:50 pm-5:39 pm

1 stop20h 49m

Chicago O'Hare Intl

Mon 9/22

10:27 am-5:15 pm

3 stops28h 48m

$643

Sao PauloChicago

VCP - ORD

VCPORD

Sao Paulo Viracopos

Thu 9/25

7:40 pm-9:58 pm

3 stops28h 18m

Chicago O'Hare Intl

Tue 9/30

10:27 am-10:40 am

2 stops22h 13m

$646

Sao PauloChicago

VCP - ORD

VCPORD

Sao Paulo Viracopos

Wed 9/24

10:50 pm-10:52 am

1 stop14h 02m

Chicago O'Hare Intl

Sun 9/28

6:44 pm-5:45 pm

1 stop21h 01m

$646

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Wed 9/24

1:45 am-10:48 pm

3 stops23h 03m

Chicago O'Hare Intl

Thu 10/2

6:30 am-5:35 am

2 stops21h 05m

$647

Sao PauloChicago

CGH - ORD

CGHORD

Sao Paulo Congonhas

Thu 9/25

6:30 am-9:58 pm

2 stops17h 28m

Chicago O'Hare Intl

Tue 9/30

6:30 am-2:05 pm

3 stops29h 35m

$647

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 60 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 August 8, 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, 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 August 13, 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 9% 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 August 13, 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 August 13, 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
7.5
Good
1,507 reviews

Comfort

7.4

Crew

8.1

Overall

7.5

Entertainment

6.8

Food

6.8

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Copa Airlines
7.5
Good
1,507 reviews
Copa Airlines
7.5
Good
1,507 reviews

Comfort

7.4

Crew

8.1

Overall

7.5

Entertainment

6.8

Food

6.8

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
United Airlines
7.4
Good
8,920 reviews
Copa Airlines
7.5
Good
1,507 reviews

Comfort

7.4

Crew

8.1

Overall

7.5

Entertainment

6.8

Food

6.8

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.

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 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 $246. On average you can expect to pay $598. The most popular route, (Sao Paulo Guarulhos Intl - Chicago O'Hare Intl), can usually be booked for $560.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
AviancaCheapest$606Average$770FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$609Average$772FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$687Average$1,022FlexibilityNo cancel feeOn-time69%
LATAM AirlinesCheapest$844Average$1,110FlexibilityNo cancel feeOn-time81%

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