Cheap flights from Chicago to Sao Paulo from $257

In general, December 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 $132. If you don’t want to visit Sao Paulo Guarulhos Intl Airport in December, then you should wait until September to fly from Chicago, when ticket prices are also cheap, with an average price of $137.

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 $936. 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 $1,137.

Our data shows that the cheapest Chicago to Sao Paulo Guarulhos Intl Airport flights are usually those with departure times in the afternoon. Our users have found flights to Sao Paulo Guarulhos Intl Airport in the afternoon for as low as $983. Flights in the evening are often more expensive with an average ticket price of $1,062.

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

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 $846 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 $639 on momondo.

You could potentially save up to 67% on your flight if you consider stops on a Chicago to Sao Paulo Guarulhos Intl Airport flight.

As of May 2026, prices for Chicago to Sao Paulo Guarulhos Intl Airport flights are approximately 61% more expensive when compared to flights at the same time last year.

Arajet, GOL, and Copa Airlines are the most popular carriers operating from Chicago to Sao Paulo Guarulhos Intl

United Airlines, Copa Airlines and Air Canada are the top three most popular airlines that fly to Sao Paulo Guarulhos Intl Airport from Chicago according to our data. United Airlines is the first choice among our users, with 64% of people opting to fly with this airline when traveling to Sao Paulo Guarulhos Intl Airport. Keep in mind that there are 8 different airlines that fly to Sao Paulo Guarulhos Intl Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 45% of flights between Chicago and Sao Paulo have experienced a delay on any given week. The average delay length over the past 12 months has been 177 minutes.

Generally, flights departing at night tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Wednesday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 46% of their flights experiencing any sort of delay.

Panama City (PTY) was the most common stop: 61% of momondo users choosing 1-stop flights on this route connected there.

Flights via Punta Cana (PUJ) offer the lowest average round-trip price of $458.

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 12h 45m.

Panama City (PTY) has the shortest average layover time for this route: 1h 50m.

2 flights are operational daily from Chicago to Sao Paulo Guarulhos Intl Airport as of May 2026. The most popular departure time for this route is 9:00PM, with 100% of flights per day taking off in the evening.

As of May 2026, 14 flights take off from Chicago and land in Sao Paulo Guarulhos Intl Airport each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.