What is the cheapest airline that flies from Sao Paulo to Chicago?

GOL, Avianca, and Copa Airlines are the most popular carriers operating from Sao Paulo to Chicago

How many flights depart from Sao Paulo to Chicago on average per week?

As of October 2025, 12 flights take off from Sao Paulo and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

What airlines fly to Chicago?

United Airlines, Avianca and LATAM Airlines are the top three most popular airlines that fly to Chicago from Sao Paulo according to our data. United Airlines is the first choice among our users, with 65% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Which layover airport offers the lowest fares from Sao Paulo to Chicago?

Flights via Punta Cana (PUJ) offer the lowest average round-trip price of $448.

How many flights depart from Sao Paulo to Chicago on average per day?

As of October 2025, 1 flights take off from Sao Paulo and land in Chicago each day. The most common flight departure time for this route is 10:00PM, with 100% of daily flights taking off in the evening.

Which layover airport has the shortest travel time from Sao Paulo to Chicago?

Flights connecting via Punta Cana (PUJ) have the shortest average one-way travel time: 13h 20m.

Which airport is the most popular layover for flights between Sao Paulo and Chicago?

Montreal (YUL) was the most common stop: 41% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest connection time from Sao Paulo to Chicago?

Punta Cana (PUJ) has the shortest average layover time for this route: 1h 09m.

When did momondo last update prices for flights from Sao Paulo to Chicago?

Prices for flights from Sao Paulo to Chicago refresh daily.

How many operators does momondo search for flights from Sao Paulo to Chicago?

There are 4 operators available for flights from Sao Paulo to Chicago as of October 2025.

How old do you have to be to fly from Sao Paulo to Chicago?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Sao Paulo to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$285 Cheap Flights from Sao Paulo to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Sao Paulo and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $770 to $1,020. The lowest price recently found on this route was $541.

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Cheap round-trip flights

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7:25 pm - 11:06 pmGRU-ORD

30h 41m2 stops

5:45 am - 10:20 pmORD-GRU

13h 35m1 stop

$541Multiple Airlines

Find Deal

Mon, Nov 17 - Mon, Nov 24

1:20 am - 8:20 pmGRU-ORD

22h 00m1 stop

5:45 am - 10:20 pmORD-GRU

13h 35m1 stop

$555Multiple Airlines

Find Deal

Sun, Nov 16 - Mon, Nov 24

9:45 pm - 1:01 pmGRU-ORD

18h 16m2 stops

8:15 pm - 8:55 amORD-GRU

33h 40m1 stop

$563Air Canada

Find Deal

Sun, Nov 9 - Sun, Nov 23

7:35 am - 1:15 pmGRU-ORD

31h 40m1 stop

2:05 pm - 4:15 pmORD-GRU

23h 10m1 stop

$584GOL

Find Deal

Sat, Nov 1 - Tue, Nov 11

9:45 pm - 2:55 pmGRU-ORD

20h 10m1 stop

2:00 pm - 8:55 amORD-GRU

15h 55m1 stop

$585Air Canada

Find Deal

Mon, Nov 17 - Mon, Nov 24

3:10 am - 1:05 amGRU-ORD

23h 55m1 stop

2:07 pm - 6:30 amORD-GRU

13h 23m1 stop

$588Copa Airlines

Find Deal

Fri, Oct 31 - Wed, Nov 19

1:40 am - 12:46 pmGRU-ORD

14h 06m1 stop

6:56 am - 12:10 amORD-GRU

14h 14m1 stop

$608Copa Airlines

Find Deal

Thu, Nov 13 - Wed, Nov 19

2:40 am - 8:20 pmGRU-ORD

20h 40m1 stop

10:20 pm - 4:15 pmORD-GRU

14h 55m1 stop

$614Avianca

Find Deal

Mon, Nov 10 - Fri, Nov 14

2:40 am - 8:20 pmGRU-ORD

20h 40m1 stop

10:20 pm - 4:15 pmORD-GRU

14h 55m1 stop

$619Avianca

Find Deal

Mon, Nov 10 - Fri, Nov 14

7:40 pm - 12:15 pmVCP-ORD

43h 35m2 stops

12:07 pm - 10:45 amORD-VCP

19h 38m2 stops

$779GOL

Find Deal

Wed, Dec 10 - Tue, Jan 20

GOL flights from Sao Paulo to Chicago

Our best GOL deals on Sao Paulo to Chicago flight tickets

GOL

Nov 1

GRU7:35 amSao Paulo Guarulhos Intl

31h 40m

1 stop

ORD1:15 pmChicago O'Hare Intl

Nov 11

ORD2:05 pmChicago O'Hare Intl

23h 10m

1 stop

GRU4:15 pmSao Paulo Guarulhos Intl

$584

Find similar

GOL

Oct 23

GRU1:45 amSao Paulo Guarulhos Intl

13h 30m

1 stop

ORD1:15 pmChicago O'Hare Intl

Oct 26

ORD2:35 pmChicago O'Hare Intl

23h 40m

1 stop

GRU4:15 pmSao Paulo Guarulhos Intl

$586

Find similar

GOL

Dec 10

VCP7:40 pmSao Paulo Viracopos

43h 35m

2 stops

ORD12:15 pmChicago O'Hare Intl

Jan 20

ORD12:07 pmChicago O'Hare Intl

19h 38m

2 stops

VCP10:45 amSao Paulo Viracopos

$779

Find similar

Copa Airlines flights from Sao Paulo to Chicago

Our best Copa Airlines deals on Sao Paulo to Chicago flight tickets

Copa Airlines

Oct 31

GRU3:10 amSao Paulo Guarulhos Intl

23h 55m

1 stop

ORD1:05 amChicago O'Hare Intl

Nov 19

ORD2:07 pmChicago O'Hare Intl

13h 23m

1 stop

GRU6:30 amSao Paulo Guarulhos Intl

$588

Find similar

Copa Airlines

Nov 13

GRU1:40 amSao Paulo Guarulhos Intl

14h 06m

1 stop

ORD12:46 pmChicago O'Hare Intl

Nov 19

ORD6:56 amChicago O'Hare Intl

14h 14m

1 stop

GRU12:10 amSao Paulo Guarulhos Intl

$608

Find similar

Copa Airlines

Nov 17

GRU5:25 amSao Paulo Guarulhos Intl

21h 40m

1 stop

ORD12:05 amChicago O'Hare Intl

Nov 24

ORD2:07 pmChicago O'Hare Intl

27h 43m

1 stop

GRU8:50 pmSao Paulo Guarulhos Intl

$617

Find similar

Fly from

Fly to

Route

Depart

Return

Price

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Mon 11/17

7:25 pm-11:06 pm

2 stops30h 41m

Chicago O'Hare Intl

Mon 11/24

5:45 am-10:20 pm

1 stop13h 35m

$541

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Sun 11/16

1:20 am-8:20 pm

1 stop22h 00m

Chicago O'Hare Intl

Mon 11/24

5:45 am-10:20 pm

1 stop13h 35m

$555

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Sun 11/9

9:45 pm-1:01 pm

2 stops18h 16m

Chicago O'Hare Intl

Sun 11/23

8:15 pm-8:55 am

1 stop33h 40m

$563

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Sat 11/1

7:35 am-1:15 pm

1 stop31h 40m

Chicago O'Hare Intl

Tue 11/11

2:05 pm-4:15 pm

1 stop23h 10m

$584

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Mon 11/17

9:45 pm-2:55 pm

1 stop20h 10m

Chicago O'Hare Intl

Mon 11/24

2:00 pm-8:55 am

1 stop15h 55m

$585

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Fri 10/31

3:10 am-1:05 am

1 stop23h 55m

Chicago O'Hare Intl

Wed 11/19

2:07 pm-6:30 am

1 stop13h 23m

$588

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Thu 11/13

1:40 am-12:46 pm

1 stop14h 06m

Chicago O'Hare Intl

Wed 11/19

6:56 am-12:10 am

1 stop14h 14m

$608

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Mon 11/10

2:40 am-8:20 pm

1 stop20h 40m

Chicago O'Hare Intl

Fri 11/14

10:20 pm-4:15 pm

1 stop14h 55m

$614

Sao PauloChicago

GRU - ORD

GRUORD

Sao Paulo Guarulhos Intl

Mon 11/10

2:40 am-8:20 pm

1 stop20h 40m

Chicago O'Hare Intl

Fri 11/14

10:20 pm-4:15 pm

1 stop14h 55m

$619

Sao PauloChicago

VCP - ORD

VCPORD

Sao Paulo Viracopos

Wed 12/10

7:40 pm-12:15 pm

2 stops43h 35m

Chicago O'Hare Intl

Tue 1/20

12:07 pm-10:45 am

2 stops19h 38m

$779

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Sao Paulo to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

Other information

What is the typical price of a round-trip flight between Sao Paulo and Chicago?

What is the cheapest month to fly to Chicago?

The month of July is, on average, the cheapest month to fly to Chicago from Sao Paulo, with most prices found around $745. If you’re not able to fly to Chicago in July, then August is your next best option. Flight prices from Sao Paulo to Chicago during August average around $787.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Monday when prices can be found for as low as $860. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Sao Paulo to Chicago for around $1,041.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Sao Paulo to Chicago during this time can be as low as $878. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $934.

What is the cheapest Sao Paulo to Chicago flight route?

Fly from Sao Paulo Guarulhos Intl to Chicago O'Hare Intl for the best Sao Paulo - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Sao Paulo when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $929 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Sao Paulo for as low as $757 on momondo.

What cabin class options are available on Sao Paulo to Chicago flights?

There are 3 cabin classes available to choose from on Sao Paulo to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Sao Paulo to Chicago flights?

You could potentially save up to 85% on your flight if you consider stops on a Sao Paulo to Chicago flight.

How have Sao Paulo to Chicago flight prices changed over time?

As of October 2025, prices for Sao Paulo to Chicago flights are approximately 23% cheaper when compared to flights at the same time last year.

When to book flights from Sao Paulo to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Sao Paulo to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Sao Paulo to Chicago (SAO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Sao Paulo to Chicago

Best Price Found	$348
Fastest flight time	10h 25m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Sao Paulo in the past 72 hours is $348. The best round-trip flight deal from Sao Paulo to Chicago found on momondo in the last 72 hours is $695.

The fastest flight from Sao Paulo to Chicago takes 10h 25m

Direct flights go from Sao Paulo to Chicago every day.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

How far is Sao Paulo to Chicago by plane?
Chicago is 5220.4 mi away from Sao Paulo. A reasonable flight in good conditions will take 13h 30m.
When did momondo last update prices for flights from Sao Paulo to Chicago?
Prices for flights from Sao Paulo to Chicago refresh daily.
How many operators does momondo search for flights from Sao Paulo to Chicago?
There are 4 operators available for flights from Sao Paulo to Chicago as of October 2025.
How old do you have to be to fly from Sao Paulo to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Sao Paulo to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Sao Paulo to Chicago?
Based on momondo bookings for flights between Sao Paulo and Chicago, the leading plane model is Boeing 787-9 Dreamliner, making up 33.92% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 21.70%, Boeing 777-300ER with 10.24%, and Airbus A350-900 with 9.01%.
What is the most popular airline from Sao Paulo to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Sao Paulo to Chicago is United Airlines (44% of total bookings). The next most popular airlines are Copa Airlines (21%), Air Canada (20%), and Avianca (15%).

Best airlines flying from Sao Paulo to Chicago

Compare and see reviews for airlines that fly from Sao Paulo to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Avianca	PriceFrom $605	Free Cancellation	Rating 6.6 2,457 reviews	Search Avianca flights
Copa Airlines	PriceFrom $609	Free Cancellation	Rating 7.6 1,557 reviews	Search Copa Airlines flights
LATAM Airlines	PriceFrom $643	Free Cancellation	Rating 7.5 1,868 reviews	Search LATAM Airlines flights
United Airlines	PriceFrom $686	Free Cancellation	Rating 7.4 8,991 reviews	Search United Airlines flights

United Airlines Flights From Sao Paulo to Chicago
United Airlines flies from Sao Paulo to Chicago around 6 times per week, with 8,991 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Sao Paulo to Chicago in the last 72 hours was $686 (round-trip), much lower than the average airfare cost of $994 for United Airlines flights on this route.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Sao Paulo to Chicago?

Finding the right flight to Chicago from Sao Paulo is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Sao Paulo to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Sao Paulo which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Sao Paulo to Chicago?

Once you have performed a search for Sao Paulo to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Sao Paulo to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Sao Paulo to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Thu 11/27

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Cheap flights from Sao Paulo to Chicago from $285

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Sao Paulo to Chicago departing on 11/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

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Filter for what you want

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Find the cheapest flights from Sao Paulo to Chicago

Cheap round-trip flights

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Cheap last minute flights

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GOL flights from Sao Paulo to Chicago

Our best GOL deals on Sao Paulo to Chicago flight tickets

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Our best Copa Airlines deals on Sao Paulo to Chicago flight tickets

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Use the filters below to find and compare flights from Sao Paulo to Chicago that are best for you.

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How to get the cheapest flight ticket from Sao Paulo to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Sao Paulo and Chicago?

What is the cheapest month to fly to Chicago?

The month of July is, on average, the cheapest month to fly to Chicago from Sao Paulo, with most prices found around $745. If you’re not able to fly to Chicago in July, then August is your next best option. Flight prices from Sao Paulo to Chicago during August average around $787.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Sao Paulo to Chicago during this time can be as low as $878. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $934.

What is the cheapest Sao Paulo to Chicago flight route?

Fly from Sao Paulo Guarulhos Intl to Chicago O'Hare Intl for the best Sao Paulo - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Sao Paulo to Chicago flights?

There are 3 cabin classes available to choose from on Sao Paulo to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Sao Paulo to Chicago flights?

You could potentially save up to 85% on your flight if you consider stops on a Sao Paulo to Chicago flight.

How have Sao Paulo to Chicago flight prices changed over time?

As of October 2025, prices for Sao Paulo to Chicago flights are approximately 23% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Sao Paulo to Chicago?

GOL, Avianca, and Copa Airlines are the most popular carriers operating from Sao Paulo to Chicago

What airlines fly to Chicago?

Which airport is the most popular layover for flights between Sao Paulo and Chicago?

Montreal (YUL) was the most common stop: 41% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Sao Paulo to Chicago?

Flights via Punta Cana (PUJ) offer the lowest average round-trip price of $448.

Which layover airport has the shortest travel time from Sao Paulo to Chicago?

Flights connecting via Punta Cana (PUJ) have the shortest average one-way travel time: 13h 20m.

Which layover airport has the shortest connection time from Sao Paulo to Chicago?

Punta Cana (PUJ) has the shortest average layover time for this route: 1h 09m.

How many flights depart from Sao Paulo to Chicago on average per day?

As of October 2025, 1 flights take off from Sao Paulo and land in Chicago each day. The most common flight departure time for this route is 10:00PM, with 100% of daily flights taking off in the evening.

How many flights depart from Sao Paulo to Chicago on average per week?

As of October 2025, 12 flights take off from Sao Paulo and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

When to book flights from Sao Paulo to Chicago

Cheap Sao Paulo to Chicago (SAO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Sao Paulo to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Sao Paulo to Chicago by plane?

When did momondo last update prices for flights from Sao Paulo to Chicago?

How many operators does momondo search for flights from Sao Paulo to Chicago?

How old do you have to be to fly from Sao Paulo to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Sao Paulo to Chicago?

What is the most popular airline from Sao Paulo to Chicago?

Best airlines flying from Sao Paulo to Chicago

Compare and see reviews for airlines that fly from Sao Paulo to Chicago with momondo

United Airlines Flights From Sao Paulo to Chicago

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Sao Paulo to Chicago?

Can I find flights from Sao Paulo to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Sao Paulo to Chicago?

I’m not ready to book a flight from Sao Paulo to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down