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$243+ Cheap flights from Guarulhos Intl, Brazil (GRU) 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
GRU — CHI
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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Cheapflights Tip: The best prices from Sao Paulo Guarulhos Intl to Chicago are usually found in November or August, booked 27 days in advance, depart on a Sunday or Wednesday and return on a Thursday

Cheap flight deals from Guarulhos Intl to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Guarulhos Intl (GRU) 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 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$580
(Booking.com)

One-way from

$243
(Kiwi.com)

Popular in

December

Cheapest in

November

Average price

$793

Good round-trip deal

$771 or less

Good one-way deal

$413 or less
Provider with most accurate pricing for Sao Paulo Guarulhos Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Sao Paulo Guarulhos Intl-Chicago (CHI) flights.
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From Sao Paulo Guarulhos Intl to Chicago (CHI)
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One-way flight from Sao Paulo Guarulhos Intl to Chicago (CHI)
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Sao Paulo Guarulhos Intl to Chicago (CHI).
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Price to beat on a one-way flight from Sao Paulo Guarulhos Intl to Chicago (CHI).
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Find flight deals from Guarulhos Intl to Chicago

Cheapest flights from Guarulhos Intl to Chicago
Explore the most affordable flight options available from Guarulhos Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.

This Booking.com deal was found by Cheapflights users on 1/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/52:40 am
GRU
-
ORD
1 stop20h 40m
Avianca
Mon 2/910:20 pm
ORD
-
GRU
1 stop24h 15m
Avianca
Deal found 1/13$580
This Air Canada deal was found by Cheapflights users on 1/14. 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 4/229:00 pm
GRU
-
ORD
1 stop15h 08m
Air Canada
Wed 5/277:00 am
ORD
-
GRU
1 stop24h 50m
Air Canada
Deal found 1/14$594
This Copa Airlines deal was found by Cheapflights users on 1/14. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/285:25 am
GRU
-
ORD
1 stop21h 39m
Copa Airlines
Sat 3/77:34 am
ORD
-
GRU
1 stop13h 41m
Copa Airlines
Deal found 1/14$595
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Tue 2/31:20 am
GRU
-
ORD
1 stop22h 00m
Avianca
Sat 2/1410:20 pm
ORD
-
GRU
1 stop14h 55m
Avianca
Deal found 1/14$596
This SmartFares deal was found by Cheapflights users on 1/15. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/15:25 pm
GRU
-
ORD
1 stop29h 55m
GOL
Sun 3/811:20 pm
ORD
-
GRU
1 stop14h 55m
GOL
Deal found 1/15$597
This Air Canada deal was found by Cheapflights users on 1/14. 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 3/49:45 pm
GRU
-
ORD
2 stops20h 25m
Air Canada
Sun 3/157:15 am
ORD
-
GRU
1 stop23h 45m
Air Canada
Deal found 1/14$598
This Air Canada deal was found by Cheapflights users on 1/14. 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 4/229:00 pm
GRU
-
ORD
1 stop15h 08m
Air Canada
Mon 4/274:15 pm
ORD
-
GRU
1 stop15h 00m
Air Canada
Deal found 1/14$599
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Sat 4/181:45 am
GRU
-
ORD
1 stop13h 30m
Multiple Airlines
Mon 6/14:30 am
ORD
-
GRU
1 stop15h 55m
Multiple Airlines
Deal found 1/14$600
This FlightHub deal was found by Cheapflights users on 1/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/52:40 am
GRU
-
ORD
1 stop20h 40m
Avianca
Sat 2/1410:20 pm
ORD
-
GRU
1 stop21h 20m
Avianca
Deal found 1/14$601
This Air Canada deal was found by Cheapflights users on 1/14. 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 4/229:00 pm
GRU
-
ORD
2 stops22h 45m
Air Canada
Sun 5/318:45 am
ORD
-
GRU
1 stop23h 05m
Air Canada
Deal found 1/14$602
This Air Canada deal was found by Cheapflights users on 1/14. 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.
Mon 3/29:45 pm
GRU
-
ORD
2 stops18h 16m
Air Canada
Wed 4/88:40 am
ORD
-
GRU
1 stop23h 10m
Air Canada
Deal found 1/14$603
This Avianca deal was found by Cheapflights users on 1/14. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/201:20 am
GRU
-
ORD
1 stop22h 00m
Avianca
Sat 1/3110:20 pm
ORD
-
GRU
1 stop21h 20m
Avianca
Deal found 1/14$604

Cheapflights Fare Finder

 
Customize your flight search to find flights from Guarulhos Intl 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 15, 2026.
Use the filters below to find and compare flights from Sao Paulo Guarulhos Intl Airport to Chicago that are best for you.

Fly from

Guarulhos Intl

Fly to

Chicago

Route

Depart

Return

Price

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Sat 1/31

3:10 am-12:04 am

1 stop23h 54m

Chicago O'Hare Intl

Sat 2/28

2:22 pm-6:30 am

1 stop13h 08m

$595

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Sat 2/7

5:25 am-12:04 am

1 stop21h 39m

Chicago O'Hare Intl

Fri 2/20

7:34 am-12:15 am

1 stop13h 41m

$656

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Sun 3/1

9:45 pm-5:30 am

Nonstop10h 45m

Chicago O'Hare Intl

Sun 3/15

10:35 am-9:30 am

1 stop20h 55m

$673

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 3/1

9:15 pm-12:46 pm

2 stops18h 31m

Chicago Midway

Sun 3/8

12:47 pm-5:40 am

1 stop14h 53m

$678

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 2/9

9:15 pm-9:53 am

1 stop15h 38m

Chicago Midway

Mon 2/23

6:00 am-5:40 am

1 stop20h 40m

$678

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Fri 2/6

9:15 pm-3:38 pm

1 stop21h 23m

Chicago Midway

Sun 2/22

10:49 am-5:20 am

2 stops15h 31m

$678

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Wed 2/11

11:45 pm-5:37 pm

2 stops20h 52m

Chicago Midway

Thu 2/19

10:49 am-5:40 am

1 stop15h 51m

$678

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 3/1

11:45 pm-11:59 am

1 stop15h 14m

Chicago Midway

Mon 3/16

12:47 pm-7:50 am

2 stops17h 03m

$678

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Tue 2/10

10:55 pm-1:40 pm

2 stops17h 45m

Chicago O'Hare Intl

Wed 2/18

11:18 am-5:40 am

1 stop15h 22m

$678

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Mon 2/9

10:15 am-11:56 pm

2 stops16h 41m

Chicago O'Hare Intl

Mon 2/23

11:19 am-5:20 am

2 stops15h 01m

$678

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Showing 1-10 of 36 results
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Compare providers for flights from Guarulhos Intl 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 Guarulhos Intl to Chicago in January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 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 Guarulhos Intl Airport-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Sao Paulo Guarulhos Intl Airport-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Sao Paulo Guarulhos Intl Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Sao Paulo Guarulhos Intl Airport-Chicago flights, Cheapflights users trust eDreams the most. eDreams 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 Guarulhos Intl Airport-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 Guarulhos Intl to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Guarulhos Intl 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 Guarulhos Intl Airport to Chicago

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

Use this chart to determine the optimal time to book a round-trip flight from Guarulhos Intl to Chicago. Price data was last updated on January 9, 2026.

Booking 27 days in advance of your planned departure date is, on average, the best time to get cheap flights from Sao Paulo Guarulhos Intl Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, December is the cheapest month in which you can book a flight from Sao Paulo Guarulhos Intl Airport to Chicago (average of $413). Flying from Sao Paulo Guarulhos Intl Airport 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 GRU to CHI?

Find hourly flight availability from Guarulhos Intl 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 15, 2026.

When flying from Sao Paulo Guarulhos Intl Airport to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Sao Paulo Guarulhos Intl Airport to Chicago

Explore weekly flight availability from Guarulhos Intl 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 15, 2026.

The most flights from GRU 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 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 Friday 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 15, 2026.
Read reviews from past customers who have flown Copa Airlines and United Airlines from Sao Paulo Guarulhos Intl Airport to Chicago. 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.
Copa Airlines
7.6
Good
1,559 reviews

Comfort

7.4

Overall

7.6

Entertainment

6.8

Food

6.8

Boarding

7.8

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it
Copa Airlines
7.6
Good
1,559 reviews
Copa Airlines
7.6
Good
1,559 reviews

Comfort

7.4

Overall

7.6

Entertainment

6.8

Food

6.8

Boarding

7.8

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it
United Airlines
7.4
Good
9,164 reviews
Copa Airlines
7.6
Good
1,559 reviews

Comfort

7.4

Overall

7.6

Entertainment

6.8

Food

6.8

Boarding

7.8

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it

Related info for your journey

Find useful and relevant information for your journey from Guarulhos Intl 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 Guarulhos Intl Airport to Chicago?

    A quick flight from Sao Paulo Guarulhos Intl Airport to Chicago can take about 10h 45m. Copa Airlines provides one of the quickest options available for as low as $673. The distance between Sao Paulo Guarulhos Intl Airport and Chicago is about 5233 mi. This flight may include one or multiple stops.

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

    Cheapflights users have booked flights from Sao Paulo Guarulhos Intl Airport to Chicago round-trip from $451. Other airlines that can offer you cheap pricing are Avianca, from $605, and United Airlines, from $684. These flights start at 46% lower than the current average price 3 months from now.

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

    The cheapest airlines for a one-way flight from Sao Paulo Guarulhos Intl Airport to Chicago are Copa Airlines ($315), Avianca ($331), and Air Canada ($546).

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

    On average you can expect to pay $1,227 for a flight from Sao Paulo Guarulhos Intl Airport to Chicago. The cheapest flight overall is $257 while the most popular route, (Sao Paulo Guarulhos Intl - Chicago O'Hare Intl) is currently priced at $461.

  • Can I find deals for flights from Guarulhos Intl to Chicago that include hotel bookings?

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

  • How can I find direct flights from Guarulhos Intl to Chicago?

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

  • Can I find deals for business class flights from Guarulhos Intl to Chicago?

    Yes. Cheapflights offers flight deals from Guarulhos Intl 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 Guarulhos Intl Airport to Chicago?

    Currently, December is the cheapest month in which you can book a flight from Sao Paulo Guarulhos Intl Airport to Chicago (average of $413). Flying from Sao Paulo Guarulhos Intl Airport 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

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Alternative routes for Guarulhos Intl 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 Guarulhos Intl to Chicago

Discover the top 3 airlines that operate flights from Guarulhos Intl 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 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$451Average$760FlexibilityNo cancel feeOn-time70%
AviancaCheapest$605Average$743FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$684Average$932FlexibilityNo cancel feeOn-time69%

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