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$310+ 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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
GRU — CHI
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Cheapflights Tip: The best prices from Sao Paulo Guarulhos Intl to Chicago are usually found in August or September, booked 7 days in advance, depart on a Monday or Tuesday 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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$539
(Mytrip)

One-way from

$310
(Kiwi.com)

Popular in

January

Cheapest in

August

Average price

$889

Good round-trip deal

$708 or less

Good one-way deal

$348 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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Highest demand for flights based on searches. 8% potential increase in price ($78 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 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 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 October 14, 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.
Mon 11/32:40 amGRU - ORD
2 stops23h 26mMultiple Airlines
Wed 11/1210:20 pmORD - GRU
1 stop14h 55mMultiple Airlines
Deal found 10/13$539
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 10/12. 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 10/305:25 pmGRU - ORD
2 stops33h 38mMultiple Airlines
Sat 11/810:20 pmORD - GRU
1 stop24h 15mMultiple Airlines
Deal found 10/12$550
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.
Mon 11/39:15 pmGRU - ORD
2 stops28h 51mMultiple Airlines
Tue 11/115:10 amORD - GRU
3 stops21h 30mMultiple Airlines
Deal found 10/13$559
This Air Canada deal was found by Cheapflights users on 10/11. 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 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 12/17:05 amORD - GRU
1 stop22h 55mAir Canada
Deal found 10/11$563
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/11:00 amGRU - ORD
2 stops36h 35mMultiple Airlines
Mon 2/165:45 amORD - GRU
1 stop13h 35mMultiple Airlines
Deal found 10/12$564
This Air Canada deal was found by Cheapflights users on 10/12. 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.
Thu 11/209:30 pmGRU - ORD
2 stops20h 25mAir Canada
Sun 11/307:05 amORD - GRU
1 stop22h 55mAir Canada
Deal found 10/12$570
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/254:25 amGRU - ORD
2 stops33h 10mMultiple Airlines
Mon 2/165:45 amORD - GRU
1 stop13h 35mMultiple Airlines
Deal found 10/12$573
This Delta deal was found by Cheapflights users on 10/12. 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.
Thu 11/2010:40 pmGRU - MDW
2 stops16h 54mDelta
Sun 11/3010:47 amMDW - GRU
1 stop15h 53mDelta
Deal found 10/12$801
This Delta deal was found by Cheapflights users on 10/12. 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.
Wed 12/2411:20 amGRU - MDW
2 stops30h 24mDelta
Tue 1/66:00 amMDW - GRU
2 stops35h 50mDelta
Deal found 10/12$807
This LATAM Airlines deal was found by Cheapflights users on 10/12. 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/279:15 pmGRU - MDW
1 stop15h 37mLATAM Airlines
Sun 12/75:13 pmMDW - GRU
1 stop13h 22mLATAM Airlines
Deal found 10/12$809
This Delta deal was found by Cheapflights users on 10/12. 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.
Fri 12/193:15 pmGRU - MDW
3 stops34h 07mDelta
Thu 1/19:29 amMDW - GRU
2 stops21h 06mDelta
Deal found 10/12$810

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 October 14, 2025.
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 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

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Sat 10/25

4:50 pm-1:15 pm

1 stop22h 25m

Chicago O'Hare Intl

Sun 11/9

1:35 pm-4:15 pm

1 stop23h 40m

$789

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Tue 11/4

9:45 pm-5:30 am

Nonstop10h 45m

Chicago O'Hare Intl

Sun 11/16

5:50 pm-7:15 am

Nonstop10h 25m

$795

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Mon 11/17

9:45 pm-5:30 am

Nonstop10h 45m

Chicago O'Hare Intl

Mon 11/24

5:50 pm-7:15 am

Nonstop10h 25m

$795

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Thu 4/9

10:20 pm-6:45 am

Nonstop10h 25m

Chicago O'Hare Intl

Sat 4/18

2:15 pm-7:35 am

1 stop15h 20m

$795

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Sun 11/30

9:45 pm-5:30 am

Nonstop10h 45m

Chicago O'Hare Intl

Mon 12/8

5:50 pm-7:15 am

Nonstop10h 25m

$795

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Mon 12/1

5:25 pm-12:15 pm

1 stop21h 50m

Chicago O'Hare Intl

Tue 12/9

2:05 pm-4:15 pm

1 stop23h 10m

$800

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 11/18

11:45 pm-11:52 am

1 stop15h 07m

Chicago Midway

Tue 11/25

12:47 pm-5:40 am

1 stop13h 53m

$801

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Fri 11/21

11:45 pm-12:46 pm

2 stops16h 01m

Chicago Midway

Sun 11/30

5:34 pm-9:35 am

1 stop13h 01m

$801

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 11/20

9:15 pm-9:52 am

1 stop15h 37m

Chicago Midway

Sun 11/30

10:47 am-9:35 am

1 stop19h 48m

$801

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 39 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 October.
ProviderPrice AccuracyTrust Score*
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 Guarulhos Intl Airport-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 Guarulhos Intl Airport-Chicago flight deals on Cheapflights vs. FlightHub >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 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 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 October 10, 2025.

Booking 7 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, May is the cheapest month in which you can book a flight from Sao Paulo Guarulhos Intl Airport to Chicago (average of $408). Flying from Sao Paulo Guarulhos Intl Airport 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 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 October 14, 2025.

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 October 14, 2025.

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).

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 14, 2025.
Read reviews from past customers who have flown 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.
United Airlines
7.4
Good
8,976 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,976 reviews
United Airlines
7.4
Good
8,976 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 $795. 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 $605. Other airlines that can offer you cheap pricing are Copa Airlines, from $609, and LATAM Airlines, from $643. These flights start at 32% lower than the current average price 3 months from now.

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

    On average you can expect to pay $762 for a flight from Sao Paulo Guarulhos Intl Airport to Chicago. The cheapest flight overall is $211 while the most popular route, (Sao Paulo Guarulhos Intl - Chicago O'Hare Intl) is currently priced at $471.

  • 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, May is the cheapest month in which you can book a flight from Sao Paulo Guarulhos Intl Airport to Chicago (average of $408). Flying from Sao Paulo Guarulhos Intl Airport 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
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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 4 airlines flying from Guarulhos Intl to Chicago

Discover the top 4 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 October 14, 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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