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Cheap flights from Chicago to Sao Paulo from $248

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 10/29. 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

LATAM Airlines Logo
5:51 pm - 2:55 pmORD-GRU
19h 04m2 stops
LATAM Airlines Logo
3:40 am - 11:57 pmGRU-ORD
22h 17m2 stops
$568LATAM Airlines
Find Deal
Mon, Oct 20 - Wed, Oct 22
LATAM Airlines Logo
4:25 pm - 9:00 amMDW-GRU
14h 35m1 stop
LATAM Airlines Logo
4:40 pm - 1:36 pmGRU-MDW
22h 56m2 stops
$568LATAM Airlines
Find Deal
Wed, Sep 3 - Tue, Sep 9
LATAM Airlines Logo
1:05 pm - 5:40 amORD-GRU
14h 35m2 stops
LATAM Airlines Logo
5:45 pm - 8:40 amGRU-ORD
16h 55m2 stops
$573LATAM Airlines
Find Deal
Wed, Sep 17 - Tue, Sep 23
Logo
7:29 pm - 5:45 pmORD-VCP
20h 16m1 stop
Logo
10:50 pm - 6:24 pmVCP-ORD
21h 34m1 stop
$574
Find Deal
Tue, Oct 21 - Tue, Oct 28
Logo
10:18 am - 8:35 amORD-VCP
19h 17m1 stop
Logo
10:50 pm - 6:23 pmVCP-ORD
22h 33m1 stop
$576
Find Deal
Fri, Nov 7 - Sun, Nov 16
LATAM Airlines Logo
3:30 pm - 4:10 pmORD-GRU
22h 40m2 stops
LATAM Airlines Logo
5:45 pm - 8:37 amGRU-ORD
16h 52m2 stops
$578LATAM Airlines
Find Deal
Wed, Sep 3 - Tue, Sep 9
Delta Logo
11:00 am - 5:40 amMDW-GRU
16h 40m1 stop
Delta Logo
10:05 am - 10:14 pmGRU-MDW
14h 09m1 stop
$820Delta
Find Deal
Sat, Oct 4 - Sat, Oct 11
Delta Logo
9:35 am - 5:40 amMDW-GRU
18h 05m2 stops
Delta Logo
10:05 am - 10:14 pmGRU-MDW
14h 09m1 stop
$824Delta
Find Deal
Sat, Oct 4 - Sat, Oct 11
GOL Logo
1:51 pm - 8:45 pmORD-CGH
28h 54m2 stops
GOL Logo
6:00 am - 10:35 pmCGH-ORD
18h 35m2 stops
$875GOL
Find Deal
Wed, Oct 22 - Wed, Oct 29
GOL Logo
2:39 pm - 6:05 amORD-CGH
37h 26m2 stops
GOL Logo
6:30 am - 10:26 pmCGH-ORD
17h 56m2 stops
$914GOL
Find Deal
Wed, Sep 17 - Wed, Sep 24

LATAM Airlines flights from Chicago to Sao Paulo

Our best LATAM Airlines deals on Chicago to Sao Paulo flight tickets
LATAM Airlines
Oct 20
ORD5:51 pmChicago O'Hare Intl
19h 04m
2 stops
GRU2:55 pmSao Paulo Guarulhos Intl
Oct 22
GRU3:40 amSao Paulo Guarulhos Intl
22h 17m
2 stops
ORD11:57 pmChicago O'Hare Intl
$568
Find similar
LATAM Airlines
Sep 17
ORD1:05 pmChicago O'Hare Intl
14h 35m
2 stops
GRU5:40 amSao Paulo Guarulhos Intl
Sep 23
GRU5:45 pmSao Paulo Guarulhos Intl
16h 55m
2 stops
ORD8:40 amChicago O'Hare Intl
$573
Find similar
LATAM Airlines
Sep 3
ORD3:30 pmChicago O'Hare Intl
22h 40m
2 stops
GRU4:10 pmSao Paulo Guarulhos Intl
Sep 9
GRU5:45 pmSao Paulo Guarulhos Intl
16h 52m
2 stops
ORD8:37 amChicago O'Hare Intl
$578
Find similar

Copa Airlines flights from Chicago to Sao Paulo

Our best Copa Airlines deals on Chicago to Sao Paulo flight tickets
Copa Airlines
Aug 26
ORD7:55 amChicago O'Hare Intl
14h 15m
1 stop
GRU12:10 amSao Paulo Guarulhos Intl
Sep 5
GRU11:10 amSao Paulo Guarulhos Intl
15h 11m
1 stop
ORD12:21 amChicago O'Hare Intl
$698
Find similar
Copa Airlines
Aug 30
ORD7:55 amChicago O'Hare Intl
14h 15m
1 stop
GRU12:10 amSao Paulo Guarulhos Intl
Sep 8
GRU11:10 amSao Paulo Guarulhos Intl
15h 11m
1 stop
ORD12:21 amChicago O'Hare Intl
$718
Find similar
Copa Airlines
Aug 29
ORD3:07 pmChicago O'Hare Intl
31h 03m
1 stop
GRU12:10 amSao Paulo Guarulhos Intl
Sep 7
GRU1:40 amSao Paulo Guarulhos Intl
24h 41m
1 stop
ORD12:21 amChicago O'Hare Intl
$792
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Sao Paulo 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 August 21, 2025.
Use the filters below to find and compare flights from Chicago to Sao Paulo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Mon 10/20

5:51 pm-2:55 pm

2 stops19h 04m

Sao Paulo Guarulhos Intl

Wed 10/22

3:40 am-11:57 pm

2 stops22h 17m

$568

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 9/3

4:25 pm-9:00 am

1 stop14h 35m

Sao Paulo Guarulhos Intl

Tue 9/9

4:40 pm-1:36 pm

2 stops22h 56m

$568

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Wed 9/17

1:05 pm-5:40 am

2 stops14h 35m

Sao Paulo Guarulhos Intl

Tue 9/23

5:45 pm-8:40 am

2 stops16h 55m

$573

ChicagoSao Paulo

ORD - VCP

ORDVCP

Chicago O'Hare Intl

Tue 10/21

7:29 pm-5:45 pm

1 stop20h 16m

Sao Paulo Viracopos

Tue 10/28

10:50 pm-6:24 pm

1 stop21h 34m

$574

ChicagoSao Paulo

ORD - VCP

ORDVCP

Chicago O'Hare Intl

Fri 11/7

10:18 am-8:35 am

1 stop19h 17m

Sao Paulo Viracopos

Sun 11/16

10:50 pm-6:23 pm

1 stop22h 33m

$576

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Wed 9/3

3:30 pm-4:10 pm

2 stops22h 40m

Sao Paulo Guarulhos Intl

Tue 9/9

5:45 pm-8:37 am

2 stops16h 52m

$578

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 10/4

11:00 am-5:40 am

1 stop16h 40m

Sao Paulo Guarulhos Intl

Sat 10/11

10:05 am-10:14 pm

1 stop14h 09m

$820

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 10/4

9:35 am-5:40 am

2 stops18h 05m

Sao Paulo Guarulhos Intl

Sat 10/11

10:05 am-10:14 pm

1 stop14h 09m

$824

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

Wed 10/22

1:51 pm-8:45 pm

2 stops28h 54m

Sao Paulo Congonhas

Wed 10/29

6:00 am-10:35 pm

2 stops18h 35m

$875

ChicagoSao Paulo

ORD - CGH

ORDCGH

Chicago O'Hare Intl

Wed 9/17

2:39 pm-6:05 am

2 stops37h 26m

Sao Paulo Congonhas

Wed 9/24

6:30 am-10:26 pm

2 stops17h 56m

$914

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

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?

The cheapest month to fly to Sao Paulo from Chicago is in March. Flight prices, which tend to average around $689, are often lower during this time because this is during the off-season. If you don’t want to visit Sao Paulo in March, then you should wait until May to fly from Chicago, when ticket prices are also cheap, with an average price of $773.

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 $998. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday 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 $1,194.

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 $1,111. 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 $939 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 $728 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 73% 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 August 2025, prices for Chicago to Sao Paulo flights are approximately 27% cheaper 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

$345

Fastest flight time

10h 10m

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 $345. The best round-trip flight deal from Chicago to Sao Paulo found on momondo in the last 72 hours is $804.
The fastest flight from Chicago to Sao Paulo takes 10h 10m
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. 12h 30m 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
Copa AirlinesPriceFrom $376Free CancellationRating
7.5
1,512 reviews
Search Copa Airlines flights
AzulPriceFrom $450Free CancellationRating
8.0
807 reviews
Search Azul flights
DeltaPriceFrom $487Free CancellationRating
7.9
7,981 reviews
Search Delta flights
LATAM AirlinesPriceFrom $494Free CancellationRating
7.5
1,844 reviews
Search LATAM Airlines flights
AviancaPriceFrom $605Free CancellationRating
6.7
2,411 reviews
Search Avianca flights
American AirlinesPriceFrom $727Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Air CanadaPriceFrom $748Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
United AirlinesPriceFrom $773Free CancellationRating
7.4
8,930 reviews
Search United Airlines 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 $773 round-trip, up to an average price of $1,090. Our users have rated United Airlines at 7.4/10.

Traveling to a place near Sao Paulo?

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

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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Find better results for your trip to Brazil

Fly into one of these airports located in Sao Paulo

Airports listed have a maximum distance of 48.9 mi from Sao Paulo
Sao Paulo Congonhas Airport
Sao Paulo Guarulhos Intl Airport
Sao Paulo Viracopos Airport