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Cheap flights from Chicago to Sao Paulo from $266

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 2/4. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:23 am - 9:15 am
ORD
-
GRU
20h 52m2 stops
Multiple Airlines Logo
11:59 pm - 6:15 pm
GRU
-
ORD
21h 16m2 stops
$548Multiple Airlines
Wed, Feb 11 - Wed, Feb 25
Arajet Logo
5:35 am - 10:25 pm
ORD
-
GRU
14h 50m1 stop
Arajet Logo
4:05 am - 10:10 pm
GRU
-
ORD
20h 05m1 stop
$552Arajet
Wed, Apr 1 - Sun, Apr 12
Multiple Airlines Logo
10:27 am - 3:10 am
ORD
-
GRU
13h 43m1 stop
Multiple Airlines Logo
5:25 pm - 9:20 pm
GRU
-
ORD
29h 55m1 stop
$579Multiple Airlines
Sat, Feb 28 - Sun, Mar 8
Multiple Airlines Logo
9:23 am - 9:15 am
ORD
-
GRU
20h 52m2 stops
Multiple Airlines Logo
5:25 pm - 12:18 am
GRU
-
ORD
33h 53m3 stops
$580Multiple Airlines
Wed, Feb 11 - Wed, Feb 25
Multiple Airlines Logo
9:23 am - 9:15 am
ORD
-
GRU
20h 52m2 stops
Multiple Airlines Logo
2:40 am - 8:20 pm
GRU
-
ORD
20h 40m1 stop
$582Multiple Airlines
Wed, Jan 21 - Tue, Jan 27
Arajet Logo
5:35 am - 10:25 pm
ORD
-
GRU
14h 50m1 stop
Arajet Logo
4:05 am - 10:10 pm
GRU
-
ORD
20h 05m1 stop
$587Arajet
Wed, May 20 - Sun, May 31
Air Canada Logo
8:40 pm - 10:35 am
ORD
-
GRU
34h 55m1 stop
Air Canada Logo
9:45 pm - 8:10 pm
GRU
-
ORD
25h 25m1 stop
$591Air Canada
Sat, Jan 17 - Fri, Jan 30
Air Canada Logo
3:45 pm - 9:45 am
ORD
-
GRU
16h 00m1 stop
Air Canada Logo
9:00 pm - 10:08 am
GRU
-
ORD
15h 08m1 stop
$598Air Canada
Fri, Apr 17 - Thu, Apr 23
LATAM Airlines Logo
6:00 am - 5:45 am
MDW
-
GRU
20h 45m2 stops
LATAM Airlines Logo
10:40 am - 10:29 pm
GRU
-
MDW
13h 49m1 stop
$629LATAM Airlines
Fri, Mar 6 - Sat, Mar 14
LATAM Airlines Logo
10:46 am - 5:45 am
MDW
-
GRU
15h 59m2 stops
LATAM Airlines Logo
11:45 pm - 11:59 am
GRU
-
MDW
15h 14m1 stop
$640LATAM Airlines
Sat, Jan 31 - Wed, Feb 11

Air Canada flights from Chicago to Sao Paulo Guarulhos Intl Airport

Our best Air Canada deals on Chicago to Sao Paulo Guarulhos Intl Airport flight tickets
Air Canada
Jan 17
ORD8:40 pmChicago O'Hare Intl
34h 55m
1 stop
GRU10:35 amSao Paulo Guarulhos Intl
Jan 30
GRU9:45 pmSao Paulo Guarulhos Intl
25h 25m
1 stop
ORD8:10 pmChicago O'Hare Intl
$591
Find similar
Air Canada
Apr 17
ORD3:45 pmChicago O'Hare Intl
16h 00m
1 stop
GRU9:45 amSao Paulo Guarulhos Intl
Apr 23
GRU9:00 pmSao Paulo Guarulhos Intl
15h 08m
1 stop
ORD10:08 amChicago O'Hare Intl
$598
Find similar
Air Canada
Apr 17
ORD8:20 pmChicago O'Hare Intl
34h 55m
1 stop
GRU9:15 amSao Paulo Guarulhos Intl
Apr 23
GRU9:00 pmSao Paulo Guarulhos Intl
15h 08m
1 stop
ORD10:08 amChicago O'Hare Intl
$602
Find similar

LATAM Airlines flights from Chicago to Sao Paulo Guarulhos Intl Airport

Our best LATAM Airlines deals on Chicago to Sao Paulo Guarulhos Intl Airport flight tickets
LATAM Airlines
Mar 6
ORD6:45 amChicago O'Hare Intl
20h 00m
2 stops
GRU5:45 amSao Paulo Guarulhos Intl
Mar 14
GRU9:00 pmSao Paulo Guarulhos Intl
15h 00m
1 stop
ORD10:00 amChicago O'Hare Intl
$629
Find similar
LATAM Airlines
Feb 12
ORD5:25 amChicago O'Hare Intl
21h 15m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Feb 23
GRU9:00 pmSao Paulo Guarulhos Intl
23h 43m
1 stop
ORD5:43 pmChicago O'Hare Intl
$640
Find similar
LATAM Airlines
May 16
MDW6:00 amChicago Midway
21h 30m
2 stops
GRU5:30 amSao Paulo Guarulhos Intl
May 30
GRU11:00 pmSao Paulo Guarulhos Intl
14h 56m
2 stops
MDW11:56 amChicago Midway
$645
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Sao Paulo Guarulhos Intl Airport 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, momondo users made 832,500 searches. Data last updated December 10, 2025.
Use the filters below to find and compare flights from Chicago to Sao Paulo Guarulhos Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Wed 2/11

9:23 am-9:15 am

2 stops20h 52m

Sao Paulo Guarulhos Intl

Wed 2/25

11:59 pm-6:15 pm

2 stops21h 16m

$548

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Wed 4/1

5:35 am-10:25 pm

1 stop14h 50m

Sao Paulo Guarulhos Intl

Sun 4/12

4:05 am-10:10 pm

1 stop20h 05m

$552

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Sat 2/28

10:27 am-3:10 am

1 stop13h 43m

Sao Paulo Guarulhos Intl

Sun 3/8

5:25 pm-9:20 pm

1 stop29h 55m

$579

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Wed 2/11

9:23 am-9:15 am

2 stops20h 52m

Sao Paulo Guarulhos Intl

Wed 2/25

5:25 pm-12:18 am

3 stops33h 53m

$580

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Wed 1/21

9:23 am-9:15 am

2 stops20h 52m

Sao Paulo Guarulhos Intl

Tue 1/27

2:40 am-8:20 pm

1 stop20h 40m

$582

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Wed 5/20

5:35 am-10:25 pm

1 stop14h 50m

Sao Paulo Guarulhos Intl

Sun 5/31

4:05 am-10:10 pm

1 stop20h 05m

$587

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Sat 1/17

8:40 pm-10:35 am

1 stop34h 55m

Sao Paulo Guarulhos Intl

Fri 1/30

9:45 pm-8:10 pm

1 stop25h 25m

$591

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Fri 4/17

3:45 pm-9:45 am

1 stop16h 00m

Sao Paulo Guarulhos Intl

Thu 4/23

9:00 pm-10:08 am

1 stop15h 08m

$598

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 3/6

6:00 am-5:45 am

2 stops20h 45m

Sao Paulo Guarulhos Intl

Sat 3/14

10:40 am-10:29 pm

1 stop13h 49m

$629

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 1/31

10:46 am-5:45 am

2 stops15h 59m

Sao Paulo Guarulhos Intl

Wed 2/11

11:45 pm-11:59 am

1 stop15h 14m

$640

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Sao Paulo from

How to get the cheapest flight ticket from Chicago to Sao Paulo Guarulhos Intl Airport

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 cheapest month to fly to Sao Paulo Guarulhos Intl Airport?

In general, April is the cheapest month to fly from Chicago to Sao Paulo Guarulhos Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $646. If you don’t want to visit Sao Paulo Guarulhos Intl Airport in April, then you should wait until February to fly from Chicago, when ticket prices are also cheap, with an average price of $663.

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

On average, the least expensive day to fly to Sao Paulo Guarulhos Intl Airport from Chicago is on a Thursday. momondo users have found tickets for Thursday departures for as low as $948. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Sao Paulo Guarulhos Intl Airport is Tuesday, with ticket prices averaging around $1,097.

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

Our data shows that the cheapest Chicago to Sao Paulo Guarulhos Intl Airport flights are usually those with departure times at noon. Our users have found flights to Sao Paulo Guarulhos Intl Airport at noon for as low as $956. Flights in the afternoon are often more expensive with an average ticket price of $1,044.

What is the cheapest Chicago to Sao Paulo Guarulhos Intl flight route?

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

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

You are more likely to see cheaper flights to Sao Paulo Guarulhos Intl Airport from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Sao Paulo Guarulhos Intl Airport for around $848 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Sao Paulo Guarulhos Intl Airport from Chicago for as low as $686 on momondo.

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

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

You could potentially save up to 63% on your flight if you consider stops on a Chicago to Sao Paulo Guarulhos Intl Airport flight.

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

As of December 2025, prices for Chicago to Sao Paulo Guarulhos Intl Airport flights are approximately 58% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Sao Paulo Guarulhos Intl Airport

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

Cheap Chicago to Sao Paulo Guarulhos Intl Airport (CHI to GRU) flight deals and tips

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

Best Price Found

$2,413

Fastest flight time

10h 15m

Direct flights

Every day
The best one-way flight to Sao Paulo Guarulhos Intl Airport from Chicago in the past 72 hours is $2,413. The best round-trip flight deal from Chicago to Sao Paulo Guarulhos Intl Airport found on momondo in the last 72 hours is $878.
The fastest flight from Chicago to Sao Paulo Guarulhos Intl Airport takes 10h 15m
Direct flights go from Chicago to Sao Paulo Guarulhos Intl Airport every day.
Search flight deals

  • How far is Chicago to Sao Paulo Guarulhos Intl by plane?

    Chicago and Sao Paulo Guarulhos Intl are 5218.7 mi apart from one another. Flights usually cover this in 10h 15m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago to Sao Paulo Guarulhos Intl Airport?

    Prices for flights from Chicago to Sao Paulo Guarulhos Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago to Sao Paulo Guarulhos Intl Airport?

  • How old do you have to be to fly from Chicago to Sao Paulo Guarulhos Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Sao Paulo Guarulhos Intl Airport.

  • What documentation or ID do you need to fly to Sao Paulo Guarulhos Intl Airport?

    The required travel and health documents for your Sao Paulo Guarulhos Intl Airport 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 Sao Paulo Guarulhos Intl Airport. 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 Chicago to Sao Paulo Guarulhos Intl Airport?

  • What is the most popular airline from Chicago to Sao Paulo Guarulhos Intl Airport?

Best airlines flying from Chicago to Sao Paulo Guarulhos Intl Airport

Compare and see reviews for airlines that fly from Chicago to Sao Paulo Guarulhos Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Copa AirlinesPriceFrom $376Free CancellationRating
7.6
1,558 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $435Free CancellationRating
7.4
9,093 reviews
Search United Airlines flights
American AirlinesPriceFrom $500Free CancellationRating
7.2
11,048 reviews
Search American Airlines flights
LATAM AirlinesPriceFrom $531Free CancellationRating
7.5
1,889 reviews
Search LATAM Airlines flights
AviancaPriceFrom $572Free CancellationRating
6.6
2,478 reviews
Search Avianca flights
GOLPriceFrom $596Free CancellationRating
7.3
1,126 reviews
Search GOL flights
DeltaPriceFrom $600Free CancellationRating
7.9
8,007 reviews
Search Delta flights
Air CanadaPriceFrom $696Free CancellationRating
7.1
10,514 reviews
Search Air Canada flights

  • United Airlines Flights From Chicago to Sao Paulo Guarulhos Intl Airport

    Across 7 United Airlines flights from Chicago to Sao Paulo Guarulhos Intl Airport this week, the average price was $993, with the best United Airlines deals starting from $435 round-trip. 9,093 users have rated United Airlines on momondo, with an average score of 7.4/10.

Traveling to a place near Sao Paulo?

Book flights to Sao Paulo if you plan to visit one of these locations
Guarulhos
Santos
Guarujá
Campinas
Aparecida

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Sao Paulo. momondo saves you time and could save you money on your trip.

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?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Sao Paulo from Chicago.

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

Yes momondo offers price alerts on flights to Sao Paulo from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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