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

14 flights are operational weekly from Chicago to Sao Paulo as of November 2025. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.

What airlines fly to Sao Paulo?

United Airlines, Copa Airlines and LATAM Airlines are the top three most popular airlines that fly to Sao Paulo from Chicago according to our data. United Airlines is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Sao Paulo. Keep in mind that there are 8 different airlines that fly to Sao Paulo on a routine basis, so you have a few additional options to choose from.

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

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

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

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 12h 45m.

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

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

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

Miami (MIA) has the shortest average layover time for this route: 1h 37m.

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

Flights via Atlanta (ATL) offer the lowest average round-trip price of $500.

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

The number of flights available between Chicago and Sao Paulo is 2 per day as of November 2025. The most frequent departure time is 5:00PM, with 77% of daily flights leaving in the afternoon.

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

Prices for flights from Chicago to Sao Paulo refresh daily.

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

As of November 2025, there are 8 operators available to choose from for flights from Chicago to Sao Paulo.

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

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 Chicago to Sao Paulo.

What documentation or ID do you need to fly to Sao Paulo?

The travel and health documents you'll need for your trip to Sao Paulo may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Sao Paulo. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$203 Cheap Flights from Chicago to Sao Paulo in 2025/26

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

Prices are currently low for flights on this route. Typical prices usually range from $606 to $1,079. The lowest price recently found on this route was $455.

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Cheap round-trip flights

Enter your travel dates to find the best prices.

11:20 pm - 4:15 pmORD-GRU

14h 55m1 stop

4:10 am - 10:10 pmGRU-ORD

20h 00m1 stop

$476Multiple Airlines

Find Deal

Sun, Mar 8 - Sun, Mar 15

10:20 pm - 1:35 amORD-GRU

24h 15m1 stop

2:40 am - 8:20 pmGRU-ORD

20h 40m1 stop

$478Avianca

Find Deal

Wed, Nov 26 - Sun, Dec 7

3:22 pm - 6:30 amORD-GRU

13h 08m1 stop

5:25 am - 1:04 amGRU-ORD

21h 39m1 stop

$488Copa Airlines

Find Deal

Sun, Mar 8 - Sun, Mar 15

6:56 am - 12:15 amORD-GRU

14h 19m1 stop

1:40 am - 12:52 pmGRU-ORD

14h 12m1 stop

$508Copa Airlines

Find Deal

Thu, Nov 27 - Sat, Dec 6

4:30 am - 10:25 pmORD-GRU

15h 55m1 stop

10:37 pm - 9:57 amGRU-ORD

13h 20m1 stop

$532Arajet

Find Deal

Mon, Apr 6 - Fri, Apr 24

6:45 am - 10:20 pmORD-GRU

13h 35m1 stop

10:37 pm - 9:57 amGRU-ORD

13h 20m1 stop

$567Arajet

Find Deal

Mon, Mar 23 - Fri, Apr 3

7:00 am - 6:55 amORD-GRU

20h 55m1 stop

4:30 pm - 12:06 pmGRU-ORD

22h 36m2 stops

$600LATAM Airlines

Find Deal

Tue, Nov 25 - Fri, Dec 5

12:46 pm - 4:30 pmMDW-GRU

24h 44m2 stops

5:45 pm - 10:15 amGRU-MDW

19h 30m2 stops

$607LATAM Airlines

Find Deal

Mon, Mar 2 - Fri, Mar 6

1:05 pm - 5:40 amMDW-GRU

14h 35m1 stop

10:50 pm - 4:25 pmGRU-MDW

19h 35m1 stop

$620Delta

Find Deal

Tue, May 5 - Tue, May 19

12:47 pm - 9:35 amMDW-GRU

17h 48m1 stop

10:20 am - 11:47 pmGRU-MDW

16h 27m2 stops

$625Delta

Find Deal

Wed, Nov 26 - Mon, Dec 8

LATAM Airlines flights from Chicago to Sao Paulo

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

LATAM Airlines

Nov 25

ORD7:00 amChicago O'Hare Intl

20h 55m

1 stop

GRU6:55 amSao Paulo Guarulhos Intl

Dec 5

GRU4:30 pmSao Paulo Guarulhos Intl

22h 36m

2 stops

ORD12:06 pmChicago O'Hare Intl

$600

Find similar

LATAM Airlines

Mar 2

MDW12:46 pmChicago Midway

24h 44m

2 stops

GRU4:30 pmSao Paulo Guarulhos Intl

Mar 6

GRU5:45 pmSao Paulo Guarulhos Intl

19h 30m

2 stops

MDW10:15 amChicago Midway

$607

Find similar

LATAM Airlines

Nov 11

ORD11:19 amChicago O'Hare Intl

19h 16m

1 stop

GRU9:35 amSao Paulo Guarulhos Intl

Nov 21

GRU8:15 amSao Paulo Guarulhos Intl

18h 47m

2 stops

ORD12:02 amChicago O'Hare Intl

$610

Find similar

Delta flights from Chicago to Sao Paulo

Our best Delta deals on Chicago to Sao Paulo flight tickets

Delta

Nov 13

ORD9:51 amChicago O'Hare Intl

16h 29m

2 stops

GRU5:20 amSao Paulo Guarulhos Intl

Nov 23

GRU11:45 pmSao Paulo Guarulhos Intl

18h 41m

1 stop

ORD3:26 pmChicago O'Hare Intl

$615

Find similar

Delta

May 5

MDW1:05 pmChicago Midway

14h 35m

1 stop

GRU5:40 amSao Paulo Guarulhos Intl

May 19

GRU10:50 pmSao Paulo Guarulhos Intl

19h 35m

1 stop

MDW4:25 pmChicago Midway

$620

Find similar

Delta

Nov 26

MDW12:47 pmChicago Midway

17h 48m

1 stop

GRU9:35 amSao Paulo Guarulhos Intl

Dec 8

GRU10:20 amSao Paulo Guarulhos Intl

16h 27m

2 stops

MDW11:47 pmChicago Midway

$625

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Sun 3/8

11:20 pm-4:15 pm

1 stop14h 55m

Sao Paulo Guarulhos Intl

Sun 3/15

4:10 am-10:10 pm

1 stop20h 00m

$476

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Wed 11/26

10:20 pm-1:35 am

1 stop24h 15m

Sao Paulo Guarulhos Intl

Sun 12/7

2:40 am-8:20 pm

1 stop20h 40m

$478

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Sun 3/8

3:22 pm-6:30 am

1 stop13h 08m

Sao Paulo Guarulhos Intl

Sun 3/15

5:25 am-1:04 am

1 stop21h 39m

$488

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Thu 11/27

6:56 am-12:15 am

1 stop14h 19m

Sao Paulo Guarulhos Intl

Sat 12/6

1:40 am-12:52 pm

1 stop14h 12m

$508

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Mon 4/6

4:30 am-10:25 pm

1 stop15h 55m

Sao Paulo Guarulhos Intl

Fri 4/24

10:37 pm-9:57 am

1 stop13h 20m

$532

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Mon 3/23

6:45 am-10:20 pm

1 stop13h 35m

Sao Paulo Guarulhos Intl

Fri 4/3

10:37 pm-9:57 am

1 stop13h 20m

$567

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Tue 11/25

7:00 am-6:55 am

1 stop20h 55m

Sao Paulo Guarulhos Intl

Fri 12/5

4:30 pm-12:06 pm

2 stops22h 36m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 3/2

12:46 pm-4:30 pm

2 stops24h 44m

Sao Paulo Guarulhos Intl

Fri 3/6

5:45 pm-10:15 am

2 stops19h 30m

$607

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 5/5

1:05 pm-5:40 am

1 stop14h 35m

Sao Paulo Guarulhos Intl

Tue 5/19

10:50 pm-4:25 pm

1 stop19h 35m

$620

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 11/26

12:47 pm-9:35 am

1 stop17h 48m

Sao Paulo Guarulhos Intl

Mon 12/8

10:20 am-11:47 pm

2 stops16h 27m

$625

Flights are sorted by cheapest round-trip flights first.

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

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 Chicago and Sao Paulo?

What is the cheapest month to fly to Sao Paulo?

The cheapest month to fly to Sao Paulo from Chicago is in January. Flight prices, which tend to average around $505, are often lower during this time because this is during the off-season. If you don’t want to visit Sao Paulo in January, then you should wait until March to fly from Chicago, when ticket prices are also cheap, with an average price of $640.

What is the cheapest day to depart on your flight to Sao Paulo?

The cheapest day to depart on your flight to Sao Paulo is on a Thursday when prices can be found for as low as $948. This is often the case because there is less demand to fly during this day of the week. On the other hand, Tuesday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,097.

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

At noon is the cheapest time of day to fly from Chicago to Sao Paulo when you can find flight prices for as low as $916. Flying to Sao Paulo at noon is an ideal time because this is during off-peak travel hours. Flights to Sao Paulo are more costly in the afternoon, with an average ticket price of $1,045. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Sao Paulo flight route?

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

How far in advance should I book a flight to Sao Paulo?

You are more likely to see cheaper flights to Sao Paulo from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Sao Paulo for around $875 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Sao Paulo from Chicago for as low as $742 on momondo.

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

There are 2 cabin classes available to choose from on Chicago to Sao Paulo 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 Chicago to Sao Paulo flights?

You could potentially save up to 74% on your flight if you consider stops on a Chicago to Sao Paulo flight.

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

As of November 2025, prices for Chicago to Sao Paulo flights are approximately 145% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Sao Paulo

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

Estimated round-trip price

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

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

Best Price Found	$303
Fastest flight time	10h 15m
Direct flights	Every day
Airports in Sao Paulo	1 airport

The best one-way flight to Sao Paulo from Chicago in the past 72 hours is $303. The best round-trip flight deal from Chicago to Sao Paulo found on momondo in the last 72 hours is $905.

The fastest flight from Chicago to Sao Paulo takes 10h 15m

Direct flights go from Chicago to Sao Paulo every day.

There is 1 airport near Sao Paulo: Sao Paulo Guarulhos Intl (GRU)

Search flight deals

How far is Chicago to Sao Paulo by plane?
The straight-line distance from Chicago to Sao Paulo is 5220.4 mi. 13h 01m is a normal flight duration for this route.
When did momondo last update prices for flights from Chicago to Sao Paulo?
Prices for flights from Chicago to Sao Paulo refresh daily.
How many operators does momondo search for flights from Chicago to Sao Paulo?
As of November 2025, there are 8 operators available to choose from for flights from Chicago to Sao Paulo.
How old do you have to be to fly from Chicago to Sao Paulo?
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 Chicago to Sao Paulo.
What documentation or ID do you need to fly to Sao Paulo?
The travel and health documents you'll need for your trip to Sao Paulo may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Sao Paulo. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Sao Paulo?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Sao Paulo is Boeing 787-10 Dreamliner (99.48% of total bookings). The next most popular plane model is Airbus A321-100/200 (0.52%).
What is the most popular airline from Chicago to Sao Paulo?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to Sao Paulo is United Airlines (40% of total bookings). The next most popular airlines are Avianca (16%), Copa Airlines (13%), and LATAM Airlines (12%).

Best airlines flying from Chicago to Sao Paulo

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

Airline	Rating	Free Cancellation	Price
Copa Airlines	PriceFrom $376	Free Cancellation	Rating 7.6 1,561 reviews	Search Copa Airlines flights
United Airlines	PriceFrom $435	Free Cancellation	Rating 7.4 9,004 reviews	Search United Airlines flights
Delta	PriceFrom $487	Free Cancellation	Rating 7.9 8,001 reviews	Search Delta flights
LATAM Airlines	PriceFrom $494	Free Cancellation	Rating 7.5 1,874 reviews	Search LATAM Airlines flights
American Airlines	PriceFrom $500	Free Cancellation	Rating 7.2 11,040 reviews	Search American Airlines flights
GOL	PriceFrom $596	Free Cancellation	Rating 7.3 1,126 reviews	Search GOL flights
Avianca	PriceFrom $605	Free Cancellation	Rating 6.6 2,469 reviews	Search Avianca flights
Air Canada	PriceFrom $696	Free Cancellation	Rating 7.1 10,416 reviews	Search Air Canada flights

United Airlines Flights From Chicago to Sao Paulo
United Airlines is one of the most popular airlines flying from Chicago to Sao Paulo, operating 7 flights/week on average for this route. A good United Airlines flight deal for Chicago to Sao Paulo starts from $435 round-trip, up to an average price of $1,001. Our users have rated United Airlines at 7.4/10.

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Why use momondo?

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

Finding the right flight to Sao Paulo from Chicago 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 Sao Paulo quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Sao Paulo from Chicago with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Sao Paulo.

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

Of course. momondo tracks the price of Chicago to Sao Paulo flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Sao Paulo trip

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Cheap flights from Chicago to Sao Paulo from $203

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Sao Paulo departing on 3/18. 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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Our best Delta deals on Chicago to Sao Paulo flight tickets

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

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 Chicago and Sao Paulo?

What is the cheapest month to fly to Sao Paulo?

What is the cheapest day to depart on your flight to Sao Paulo?

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

What is the cheapest Chicago to Sao Paulo flight route?

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

How far in advance should I book a flight to Sao Paulo?

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

There are 2 cabin classes available to choose from on Chicago to Sao Paulo 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 Chicago to Sao Paulo flights?

You could potentially save up to 74% on your flight if you consider stops on a Chicago to Sao Paulo flight.

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

As of November 2025, prices for Chicago to Sao Paulo flights are approximately 145% more expensive when compared to flights at the same time last year.

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

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

What airlines fly to Sao Paulo?

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

Panama City (PTY) 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 Chicago to Sao Paulo?

Flights via Atlanta (ATL) offer the lowest average round-trip price of $500.

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

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 12h 45m.

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

Miami (MIA) has the shortest average layover time for this route: 1h 37m.

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

The number of flights available between Chicago and Sao Paulo is 2 per day as of November 2025. The most frequent departure time is 5:00PM, with 77% of daily flights leaving in the afternoon.

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

14 flights are operational weekly from Chicago to Sao Paulo as of November 2025. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.

When to book flights from Chicago to Sao Paulo

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Sao Paulo

How far is Chicago to Sao Paulo by plane?

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

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

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

What documentation or ID do you need to fly to Sao Paulo?

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

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

Best airlines flying from Chicago to Sao Paulo

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

United Airlines Flights From Chicago to Sao Paulo

Traveling to a place near Sao Paulo?

Why use momondo?

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

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

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

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

An easier way to manage your Sao Paulo 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

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Brazil