$1,318 Cheap Flights from Chicago (MDW) to São Paulo (GRU)

View $1,318 flight on Wed, Mar 11, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to São Paulo/Guarulhos Intl. Airport

    notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
    deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
    trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Chicago to São Paulo (MDW-GRU)

Prices were available within the past 7 days and start at $1,318 for one-way flights and $620 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

LATAM Airlines Group
Thu, Nov 13 - Thu, Nov 20
MDW
Chicago
GRU
Sao Paulo
$620 Roundtrip, found 1 hour ago
$620
Roundtrip
found 1 hour ago
Select LATAM Airlines Group flight, departing Thu, Nov 13 from Chicago to Sao Paulo, returning Thu, Nov 20, priced at $620 found 1 hour ago
LATAM Airlines Group
Thu, Nov 13 - Thu, Nov 20
MDW
Chicago
GRU
Sao Paulo
$625 Roundtrip, found 1 hour ago
$625
Roundtrip
found 1 hour ago
Select LATAM Airlines Group flight, departing Thu, Nov 13 from Chicago to Sao Paulo, returning Thu, Nov 20, priced at $625 found 1 hour ago
LATAM Airlines Group
Sun, Nov 9 - Mon, Nov 17
MDW
Chicago
GRU
Sao Paulo
$628 Roundtrip, found 17 hours ago
$628
Roundtrip
found 17 hours ago
Select LATAM Airlines Group flight, departing Sun, Nov 9 from Chicago to Sao Paulo, returning Mon, Nov 17, priced at $628 found 17 hours ago
LATAM Airlines Group
Sun, Nov 9 - Mon, Nov 17
MDW
Chicago
GRU
Sao Paulo
$630 Roundtrip, found 17 hours ago
$630
Roundtrip
found 17 hours ago
Select LATAM Airlines Group flight, departing Sun, Nov 9 from Chicago to Sao Paulo, returning Mon, Nov 17, priced at $630 found 17 hours ago
LATAM Airlines Group
Mon, Nov 17 - Mon, Nov 24
MDW
Chicago
GRU
Sao Paulo
$630 Roundtrip, found 3 days ago
$630
Roundtrip
found 3 days ago
Select LATAM Airlines Group flight, departing Mon, Nov 17 from Chicago to Sao Paulo, returning Mon, Nov 24, priced at $630 found 3 days ago
LATAM Airlines Group
Wed, Nov 5 - Sat, Nov 15
MDW
Chicago
GRU
Sao Paulo
$633 Roundtrip, found 1 day ago
$633
Roundtrip
found 1 day ago
Select LATAM Airlines Group flight, departing Wed, Nov 5 from Chicago to Sao Paulo, returning Sat, Nov 15, priced at $633 found 1 day ago
LATAM Airlines Group
Mon, Nov 10 - Sat, Nov 22
MDW
Chicago
GRU
Sao Paulo
$635 Roundtrip, found 1 day ago
$635
Roundtrip
found 1 day ago
Select LATAM Airlines Group flight, departing Mon, Nov 10 from Chicago to Sao Paulo, returning Sat, Nov 22, priced at $635 found 1 day ago
LATAM Airlines Group
Sun, Nov 9 - Sun, Nov 16
MDW
Chicago
GRU
Sao Paulo
$635 Roundtrip, found 23 hours ago
$635
Roundtrip
found 23 hours ago
Select LATAM Airlines Group flight, departing Sun, Nov 9 from Chicago to Sao Paulo, returning Sun, Nov 16, priced at $635 found 23 hours ago
LATAM Airlines Group
Sun, Nov 9 - Mon, Nov 17
MDW
Chicago
GRU
Sao Paulo
$637 Roundtrip, found 17 hours ago
$637
Roundtrip
found 17 hours ago
Select LATAM Airlines Group flight, departing Sun, Nov 9 from Chicago to Sao Paulo, returning Mon, Nov 17, priced at $637 found 17 hours ago
Delta
Tue, Nov 25 - Tue, Dec 2
MDW
Chicago
GRU
Sao Paulo
$830 Roundtrip, found 3 days ago
$830
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Nov 25 from Chicago to Sao Paulo, returning Tue, Dec 2, priced at $830 found 3 days ago

Alternative airports near São Paulo

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Guarulhos - Governor Andre Franco Montoro Intl. GRU. Cheapest option available. Average driving time to city center is 22 minutes. Flights from $2,320
GRU
Guarulhos - Governor Andre Franco Montoro Intl.
Cheapest
Average driving time to city center22 min
Flights from $2,320

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Guarulhos - Governor Andre Franco Montoro Intl. Airport (GRU) cost?
Lock in a cheap one-way flight from $1,318 or cheap return flight from $620 from Midway Intl. Airport (MDW) to Guarulhos - Governor Andre Franco Montoro Intl. Airport (GRU) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Guarulhos - Governor Andre Franco Montoro Intl. Airport (GRU)?
The cheapest month to fly from MDW to GRU is November, when demand is low. Off-peak season is often when you'll find cheap fares for travel between these airports.
Which airlines fly direct from Midway Intl. Airport (MDW) to Guarulhos - Governor Andre Franco Montoro Intl. Airport (GRU)?
You can't fly directly from Chicago, IL (MDW-Midway Intl.) to Guarulhos - Governor Andre Franco Montoro Intl. Airport (GRU). However, you can find other airports that offer nonstop flights. Board your plane at O'Hare Intl. Airport (ORD) and travel straight to Sao Paulo without any detours.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Guarulhos - Governor Andre Franco Montoro Intl. Airport (GRU)?
To find the cheapest airline flying from MDW to GRU, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from Midway Intl. Airport (MDW) to Guarulhos - Governor Andre Franco Montoro Intl. Airport (GRU)?
There are no daily nonstop flights from Midway Intl. Airport (MDW) to Guarulhos - Governor Andre Franco Montoro Intl. Airport (GRU). But you can choose flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from MDW to GRU?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Guarulhos - Governor Andre Franco Montoro Intl. Airport (GRU)?
Select a flight from Midway Intl. Airport (MDW) to Guarulhos - Governor Andre Franco Montoro Intl. Airport (GRU) that takes off before 3 PM to reduce the likelihood of delays and cancellations. Departures after this time are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Guarulhos - Governor Andre Franco Montoro Intl. Airport (GRU) last-minute?
Booking your ticket from MDW to GRU shortly before your getaway is usually more expensive. However, if you're flexible with your schedule, you could grab a cheap last-minute fare.
Is it cheaper to book a MDW to GRU flight and hotel package?
Booking a MDW to GRU flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Choose from our wide range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Guarulhos - Governor Andre Franco Montoro Intl. Airport (GRU)?
Typically, it's possible to cancel or reschedule your MDW to GRU flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Guarulhos - Governor André Franco Montoro Intl.
Airlines serving
Delta, LATAM Airlines Group
Roundtrip price
$620
Distance
5220 mi

Book with confidence

Chicago to São Paulo Flights

The cheapest times to fly from Chicago to São Paulo

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to São Paulo are during the month of November. You can find some of the cheapest flights from Chicago to São Paulo with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to São Paulo

Sunday is one of the best days to book for cheap flights from Chicago to São Paulo: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to São Paulo

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to São Paulo in 2025. You can also book with separate airlines for your outbound and return journeys, from $1,318 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to São Paulo flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to São Paulo airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to São Paulo Flights

Explore a world of travel with Expedia

*Available to One Key members.