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$281+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAO
jul. 8 — jul. 151
mar. 7/8
mar. 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Sao Paulo are usually found in March or May, booked 55 days in advance, depart on a Thursday or Monday and return on a Monday

Cheap 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 julio 3, 2025.

Round-trip from

$635
(Mytrip)

One-way from

$281
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$995

Good round-trip deal

$802 or less

Good one-way deal

$345 or less
From Chicago (CHI) to Sao Paulo (SAO)
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One-way flight from Chicago (CHI) to Sao Paulo (SAO)
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Highest demand for flights based on searches. 8% potential increase in price ($82 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Sao Paulo (SAO).
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Price to beat on a one-way flight from Chicago (CHI) to Sao Paulo (SAO).
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Find 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 julio 3, 2025.

This Mytrip deal was found by Cheapflights users on 7/1. 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.
jue. 8/146:56 amORD - VCP
2 stops32h 49mMultiple Airlines
jue. 8/216:05 amVCP - ORD
2 stops18h 17mMultiple Airlines
Deal found 7/1$635
This Mytrip deal was found by Cheapflights users on 7/2. 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.
dom. 8/172:35 pmORD - GRU
1 stop32h 05mMultiple Airlines
dom. 8/2410:10 pmGRU - ORD
3 stops27h 49mMultiple Airlines
Deal found 7/2$636
This Priceline deal was found by Cheapflights users on 7/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/272:35 pmORD - GRU
1 stop13h 00mAvianca
vie. 9/121:45 amGRU - ORD
1 stop13h 30mAvianca
Deal found 7/2$637
This FlightHub deal was found by Cheapflights users on 7/2. 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.
vie. 9/126:30 pmMDW - GRU
2 stops20h 05mLATAM Airlines
mié. 9/1710:05 amGRU - MDW
1 stop13h 31mLATAM Airlines
Deal found 7/2$637
This Mytrip deal was found by Cheapflights users on 7/1. 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.
mar. 9/26:56 amORD - CGH
2 stops25h 29mMultiple Airlines
mar. 9/96:10 amCGH - ORD
2 stops17h 48mMultiple Airlines
Deal found 7/1$645
This FlightHub deal was found by Cheapflights users on 7/2. 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.
mar. 11/251:16 pmORD - GRU
2 stops20h 24mLATAM Airlines
sáb. 11/298:15 amGRU - ORD
2 stops18h 38mLATAM Airlines
Deal found 7/2$653
This Copa Airlines deal was found by Cheapflights users on 7/2. 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.
mié. 7/301:07 amORD - GRU
1 stop21h 03mCopa Airlines
jue. 8/75:25 amGRU - ORD
1 stop20h 56mCopa Airlines
Deal found 7/2$661
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
jue. 8/149:12 pmMDW - GRU
2 stops28h 38mMultiple Airlines
jue. 8/2111:55 amGRU - MDW
1 stop22h 27mMultiple Airlines
Deal found 7/1$709
This GOL deal was found by Cheapflights users on 7/1. 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.
jue. 9/412:00 pmORD - VCP
2 stops20h 40mGOL
dom. 9/75:55 pmVCP - ORD
2 stops31h 53mGOL
Deal found 7/1$729
This GOL deal was found by Cheapflights users on 7/3. 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.
mié. 9/312:00 pmORD - CGH
2 stops22h 35mGOL
mar. 9/96:30 amCGH - ORD
2 stops19h 18mGOL
Deal found 7/3$735
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
lun. 10/68:29 amMDW - VCP
1 stop19h 06mMultiple Airlines
dom. 10/1912:45 pmVCP - MDW
2 stops20h 35mMultiple Airlines
Deal found 7/1$855
This Delta deal was found by Cheapflights users on 7/2. 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.
lun. 12/81:05 pmMDW - GRU
1 stop17h 30mDelta
mar. 2/107:30 pmGRU - MDW
2 stops17h 26mDelta
Deal found 7/2$1,059

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 julio 3, 2025.
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 - VCP

ORDVCP

Chicago O'Hare Intl

jue. 8/14

6:56 am-5:45 pm

2 stops32h 49m

Sao Paulo Viracopos

jue. 8/21

6:05 am-10:22 pm

2 stops18h 17m

$635

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

dom. 8/17

2:35 pm-12:40 am

1 stop32h 05m

Sao Paulo Guarulhos Intl

dom. 8/24

10:10 pm-11:59 pm

3 stops27h 49m

$636

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

mié. 8/27

2:35 pm-5:35 am

1 stop13h 00m

Sao Paulo Guarulhos Intl

vie. 9/12

1:45 am-1:15 pm

1 stop13h 30m

$637

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

vie. 9/12

6:30 pm-4:35 pm

2 stops20h 05m

Sao Paulo Guarulhos Intl

mié. 9/17

10:05 am-9:36 pm

1 stop13h 31m

$637

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

dom. 8/17

7:55 am-6:30 am

1 stop20h 35m

Sao Paulo Guarulhos Intl

lun. 8/25

3:10 am-12:21 am

1 stop23h 11m

$644

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

mar. 9/2

6:56 am-10:25 am

2 stops25h 29m

Sao Paulo Congonhas

mar. 9/9

6:10 am-9:58 pm

2 stops17h 48m

$645

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

dom. 7/6

9:49 am-9:00 am

1 stop21h 11m

Sao Paulo Guarulhos Intl

mar. 7/8

6:40 pm-8:40 am

2 stops16h 00m

$678

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

jue. 8/14

9:12 pm-3:50 am

2 stops28h 38m

Sao Paulo Guarulhos Intl

jue. 8/21

11:55 am-8:22 am

1 stop22h 27m

$709

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

mié. 9/3

12:00 pm-12:35 pm

2 stops22h 35m

Sao Paulo Congonhas

mar. 9/9

6:30 am-11:48 pm

2 stops19h 18m

$735

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

jue. 8/7

1:09 pm-9:00 am

2 stops17h 51m

Sao Paulo Guarulhos Intl

jue. 8/14

10:50 pm-12:28 pm

2 stops15h 38m

$814

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 24 results
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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 June 27, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Sao Paulo, you should look to book at least 55 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, April is the cheapest month in which you can book a flight from Chicago to Sao Paulo (average of $686). Flying from Chicago to Sao Paulo in December is currently the most expensive (average of $1,209). 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 julio 3, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 23% on flights from Chicago to Sao Paulo by exploring options for tickets at noon.

What is the cheapest day to fly from Chicago to Sao Paulo?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Sao Paulo. Price data was last updated on December 1, 2024.

Travelers seeking maximum savings on their Chicago to Sao Paulo flight should consider departing on Sunday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 julio 3, 2025.

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?

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 julio 3, 2025.
Read reviews from past customers who have flown Azul, Delta, and LATAM Airlines 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.
Azul
8.0
Very good
790 reviews

Comfort

7.9

Entertainment

7.5

Boarding

8.1

Food

7.1

Overall

8.0

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
790 reviews
Azul
8.0
Very good
790 reviews

Comfort

7.9

Entertainment

7.5

Boarding

8.1

Food

7.1

Overall

8.0

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
7,982 reviews
Azul
8.0
Very good
790 reviews

Comfort

7.9

Entertainment

7.5

Boarding

8.1

Food

7.1

Overall

8.0

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
1,805 reviews
Azul
8.0
Very good
790 reviews

Comfort

7.9

Entertainment

7.5

Boarding

8.1

Food

7.1

Overall

8.0

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
1,467 reviews
Azul
8.0
Very good
790 reviews

Comfort

7.9

Entertainment

7.5

Boarding

8.1

Food

7.1

Overall

8.0

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
8,861 reviews
Azul
8.0
Very good
790 reviews

Comfort

7.9

Entertainment

7.5

Boarding

8.1

Food

7.1

Overall

8.0

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 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.

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

    According to our current data, Avianca ($637), LATAM Airlines ($637), and Copa Airlines ($644) offers the cheapest pricing from Chicago to Sao Paulo. Avianca is priced at 32% 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 Avianca, with whom users have recently found tickets for as low as $297. However, be on the lookout for offers from Copa Airlines and Arajet, 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 $914, our data shows the cheapest flight currently is $309. When looking at the most popular route, (Chicago O'Hare Intl - Sao Paulo Guarulhos Intl), you can expect to pay $506 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, April is the cheapest month in which you can book a flight from Chicago to Sao Paulo (average of $686). Flying from Chicago to Sao Paulo in December is currently the most expensive (average of $1,209). 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 8 airlines flying from Chicago to Sao Paulo

Discover the top 8 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 julio 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$376Average$695FlexibilityNo cancel feeOn-time70%
AzulCheapest$450Average$1,716FlexibilityNo cancel feeOn-time82%
DeltaCheapest$487Average$677FlexibilityNo cancel feeOn-timeN/A
LATAM AirlinesCheapest$494Average$649FlexibilityNo cancel feeOn-time81%
AviancaCheapest$605Average$864FlexibilityNo cancel feeOn-time71%
American AirlinesCheapest$727Average$988FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$748Average$1,016FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$773Average$1,131FlexibilityNo cancel feeOn-time69%

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