Cheap Flights from Chicago to São Paulo from £352 Return

Flight deals from Chicago to São Paulo

Looking for cheap tickets from Chicago to São Paulo, or a last-minute trip? Find the lowest prices on one-way and return tickets right here.

Sao Paulo.£352 per passenger.Departing Wed, 22 Oct, returning Wed, 29 Oct.Return flight with GOL Linhas Aéreas and Azul Airlines.Outbound indirect flight with GOL Linhas Aéreas, departs from Chicago O'Hare International on Wed, 22 Oct, arriving in Sao Paulo Guarulhos.Inbound indirect flight with Azul Airlines, departs from Sao Paulo Congonhas on Wed, 29 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From £352, select.

Ribeirao Preto.£554 per passenger.Departing Tue, 18 Nov, returning Sun, 23 Nov.Return flight with Copa and GOL Linhas Aéreas.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Tue, 18 Nov, arriving in Ribeirao Preto.Inbound indirect flight with GOL Linhas Aéreas, departs from Ribeirao Preto on Sun, 23 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From £554, select.

Sao Jose Dos Campos.£725 per passenger.Departing Thu, 20 Nov, returning Thu, 27 Nov.Return flight with Frontier Airlines and GOL Linhas Aéreas.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 20 Nov, arriving in Sao Jose Dos Campos.Inbound indirect flight with GOL Linhas Aéreas, departs from Sao Jose Dos Campos on Thu, 27 Nov, arriving in Chicago Midway.Price includes taxes and charges.From £725, select.

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Flying from Chicago to São Paulo

Arm yourself with these facts on the fly.

Cheapest flight found	£352
Cheapest month to fly	October
Average flight time	10 hrs, 19 mins
Cheapest airport to fly from	Chicago O'Hare International
Most popular airline	United

How to find cheap flights from Chicago to São Paulo

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago to São Paulo. Other savvy travellers recently found return flights from £352 and one-way tickets from £150 one-way. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago O'Hare International into Sao Paulo Guarulhos

At the moment, the lowest priced flight tickets to São Paulo are from Chicago O'Hare International Airport to Sao Paulo Guarulhos Airport.

Fly in October

We crunched the flight calendar and found the cheapest time to fly from Chicago to São Paulo is currently October.

Flex your dates for the best rates

If you’re flexible on your departure dates, you can use Skyscanner's whole month tool to find the cheapest day of the year to fly from Chicago to anywhere you choose in São Paulo.

Watch as fares rise and fall

With Price Alerts, we'll let you know when flight prices from Chicago to São Paulo go up or down so you can book when the time is just right.

Relax – these are fee-free flight tickets

With us, there are no added fees – the São Paulo to São Paulo flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

What's the average Chicago to São Paulo flight price?

We looked at all of the upcoming return flights from Chicago to São Paulo we could find over the next 12 months. It looks like £352 is the best price. This is good, compared to the average São Paulo ticket price of £544.

What is the cheapest month to fly from Chicago to São Paulo?

The cheapest month to fly from Chicago to Sao Jose Dos Campos Airport is currently November. The cheapest month to fly from Chicago to Sao Paulo Guarulhos Airport is usually October. And the cheapest month to fly from Chicago to Ribeirao Preto Airport is usually November.

Which upcoming date is cheapest to fly from Chicago to São Paulo on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to São Paulo on Wednesday, 22 October 2025.

Are there any direct flights from Chicago to São Paulo?

Chicago O'Hare International Airport offers direct flights to São Paulo.

If I'm flying from Chicago, where in São Paulo is cheapest to fly into?

If you're flying from Chicago, the cheapest city in São Paulo to fly into is Sao Paulo. The cheapest airport serving Sao Paulo at the moment is Sao Paulo Guarulhos.