Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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 11/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Sao Paulo

Cheap round-trip flights

Enter your travel dates to find the best prices.
Copa Airlines Logo
6:56 am - 3:50 amORD-GRU
17h 54m1 stop
Copa Airlines Logo
5:25 am - 12:05 amGRU-ORD
21h 40m1 stop
$448Copa Airlines
Find Deal
Sun, Nov 9 - Tue, Nov 18
Avianca Logo
10:20 pm - 4:15 pmORD-GRU
14h 55m1 stop
Avianca Logo
7:35 am - 8:20 pmGRU-ORD
15h 45m1 stop
$478Avianca
Find Deal
Sun, Nov 9 - Wed, Nov 19
Avianca Logo
10:20 pm - 10:40 pmORD-GRU
21h 20m1 stop
Avianca Logo
7:35 am - 8:20 pmGRU-ORD
15h 45m1 stop
$484Avianca
Find Deal
Thu, Nov 13 - Sun, Nov 23
Copa Airlines Logo
6:56 am - 12:15 amORD-GRU
14h 19m1 stop
Copa Airlines Logo
3:10 am - 12:05 amGRU-ORD
23h 55m1 stop
$488Copa Airlines
Find Deal
Wed, Nov 19 - Tue, Nov 25
United Airlines Logo
7:10 am - 9:30 amORD-GRU
23h 20m1 stop
United Airlines Logo
9:45 pm - 5:30 amGRU-ORD
10h 45mnonstop
$490United Airlines
Find Deal
Thu, Nov 20 - Sun, Nov 30
United Airlines Logo
8:50 am - 9:30 amORD-GRU
21h 40m1 stop
United Airlines Logo
9:30 pm - 9:48 amGRU-ORD
15h 18m1 stop
$500United Airlines
Find Deal
Thu, Nov 20 - Sun, Nov 30
Air Canada Logo
7:05 am - 9:00 amORD-GRU
22h 55m1 stop
Air Canada Logo
9:45 pm - 8:10 pmGRU-ORD
25h 25m1 stop
$577Air Canada
Find Deal
Thu, Nov 27 - Thu, Dec 11
Air Canada Logo
2:00 pm - 9:00 amORD-GRU
16h 00m2 stops
Air Canada Logo
9:45 pm - 2:55 pmGRU-ORD
20h 10m1 stop
$582Air Canada
Find Deal
Thu, Nov 27 - Thu, Dec 11
LATAM Airlines Logo
9:51 am - 5:40 amORD-GRU
16h 49m1 stop
LATAM Airlines Logo
10:40 pm - 12:43 pmGRU-ORD
17h 03m1 stop
$584LATAM Airlines
Find Deal
Tue, Nov 25 - Fri, Dec 5
LATAM Airlines Logo
1:05 pm - 5:40 amMDW-GRU
13h 35m1 stop
LATAM Airlines Logo
3:20 pm - 3:25 pmGRU-MDW
27h 05m2 stops
$607LATAM Airlines
Find Deal
Mon, Mar 2 - Fri, Mar 6

Delta flights from Chicago to Sao Paulo

Our best Delta deals on Chicago to Sao Paulo flight tickets
Delta
Nov 23
MDW10:47 amChicago Midway
19h 48m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Dec 2
GRU9:15 pmSao Paulo Guarulhos Intl
15h 26m
1 stop
MDW9:41 amChicago Midway
$610
Find similar
Delta
Nov 26
MDW5:34 pmChicago Midway
13h 01m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Dec 8
GRU11:45 pmSao Paulo Guarulhos Intl
15h 49m
2 stops
MDW12:34 pmChicago Midway
$615
Find similar
Delta
Nov 6
MDW10:40 amChicago Midway
16h 00m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Nov 9
GRU9:15 pmSao Paulo Guarulhos Intl
18h 19m
2 stops
MDW12:34 pmChicago Midway
$625
Find similar

Avianca flights from Chicago to Sao Paulo

Our best Avianca deals on Chicago to Sao Paulo flight tickets
Avianca
Nov 9
ORD10:20 pmChicago O'Hare Intl
14h 55m
1 stop
GRU4:15 pmSao Paulo Guarulhos Intl
Nov 19
GRU7:35 amSao Paulo Guarulhos Intl
15h 45m
1 stop
ORD8:20 pmChicago O'Hare Intl
$478
Find similar
Avianca
Nov 13
ORD10:20 pmChicago O'Hare Intl
21h 20m
1 stop
GRU10:40 pmSao Paulo Guarulhos Intl
Nov 23
GRU7:35 amSao Paulo Guarulhos Intl
15h 45m
1 stop
ORD8:20 pmChicago O'Hare Intl
$484
Find similar
Avianca
Nov 5
ORD10:20 pmChicago O'Hare Intl
21h 20m
1 stop
GRU10:40 pmSao Paulo Guarulhos Intl
Nov 8
GRU2:40 amSao Paulo Guarulhos Intl
20h 40m
1 stop
ORD8:20 pmChicago O'Hare Intl
$485
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 October 23, 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

Sun 11/9

6:56 am-3:50 am

1 stop17h 54m

Sao Paulo Guarulhos Intl

Tue 11/18

5:25 am-12:05 am

1 stop21h 40m

$448

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Sun 11/9

10:20 pm-4:15 pm

1 stop14h 55m

Sao Paulo Guarulhos Intl

Wed 11/19

7:35 am-8:20 pm

1 stop15h 45m

$478

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Thu 11/13

10:20 pm-10:40 pm

1 stop21h 20m

Sao Paulo Guarulhos Intl

Sun 11/23

7:35 am-8:20 pm

1 stop15h 45m

$484

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Wed 11/19

6:56 am-12:15 am

1 stop14h 19m

Sao Paulo Guarulhos Intl

Tue 11/25

3:10 am-12:05 am

1 stop23h 55m

$488

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Thu 11/20

7:10 am-9:30 am

1 stop23h 20m

Sao Paulo Guarulhos Intl

Sun 11/30

9:45 pm-5:30 am

Nonstop10h 45m

$490

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Thu 11/20

8:50 am-9:30 am

1 stop21h 40m

Sao Paulo Guarulhos Intl

Sun 11/30

9:30 pm-9:48 am

1 stop15h 18m

$500

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Thu 11/27

7:05 am-9:00 am

1 stop22h 55m

Sao Paulo Guarulhos Intl

Thu 12/11

9:45 pm-8:10 pm

1 stop25h 25m

$577

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Thu 11/27

2:00 pm-9:00 am

2 stops16h 00m

Sao Paulo Guarulhos Intl

Thu 12/11

9:45 pm-2:55 pm

1 stop20h 10m

$582

ChicagoSao Paulo

ORD - GRU

ORDGRU

Chicago O'Hare Intl

Tue 11/25

9:51 am-5:40 am

1 stop16h 49m

Sao Paulo Guarulhos Intl

Fri 12/5

10:40 pm-12:43 pm

1 stop17h 03m

$584

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 3/2

1:05 pm-5:40 am

1 stop13h 35m

Sao Paulo Guarulhos Intl

Fri 3/6

3:20 pm-3:25 pm

2 stops27h 05m

$607

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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 $977. 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 $878 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 72% 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 October 2025, prices for Chicago to Sao Paulo flights are approximately 16% 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

$303

Fastest flight time

10h 25m

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 $605.
The fastest flight from Chicago to Sao Paulo takes 10h 25m
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?

  • 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
7.6
1,560 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $435Free CancellationRating
7.4
8,992 reviews
Search United Airlines flights
DeltaPriceFrom $487Free CancellationRating
7.9
7,981 reviews
Search Delta flights
LATAM AirlinesPriceFrom $494Free CancellationRating
7.5
1,871 reviews
Search LATAM Airlines flights
American AirlinesPriceFrom $500Free CancellationRating
7.2
11,031 reviews
Search American Airlines flights
GOLPriceFrom $596Free CancellationRating
7.3
1,117 reviews
Search GOL flights
AviancaPriceFrom $605Free CancellationRating
6.6
2,460 reviews
Search Avianca flights
Air CanadaPriceFrom $696Free CancellationRating
7.1
10,347 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 3 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 $999. 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

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 11/22
Sat 11/29
By creating a price alert you accept our terms of use and privacy policy.

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