Cheap flights from Chicago to Sao Paulo from $257

The cheapest month to fly to Sao Paulo from Chicago is in December. Flight prices, which tend to average around $132, are often lower during this time because this is during the off-season. If you don’t want to visit Sao Paulo in December, then you should wait until September to fly from Chicago, when ticket prices are also cheap, with an average price of $137.

The cheapest day to depart on your flight to Sao Paulo is on a Thursday when prices can be found for as low as $956. 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 $1,185.

In the afternoon is the cheapest time of day to fly from Chicago to Sao Paulo when you can find flight prices for as low as $992. Flying to Sao Paulo in the afternoon is an ideal time because this is during off-peak travel hours. Flights to Sao Paulo are more costly in the evening, with an average ticket price of $1,087. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

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

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 $846 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 $639 on momondo.

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.

You could potentially save up to 32% on your flight if you consider stops on a Chicago to Sao Paulo flight.

As of May 2026, prices for Chicago to Sao Paulo flights are approximately 50% cheaper when compared to flights at the same time last year.

Arajet, GOL, and Azul are the most popular carriers operating from Chicago to Sao Paulo

United Airlines, Copa Airlines and Air Canada are the top three most popular airlines that fly to Sao Paulo from Chicago according to our data. United Airlines is the first choice among our users, with 65% of people opting to fly with this airline when traveling to Sao Paulo. Keep in mind that there are 8 different airlines that fly to Sao Paulo on a routine basis, so you have a few additional options to choose from.

Historically, on average around 47% 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 176 minutes.

Generally, flights departing in the early afternoon 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 47% of their flights experiencing any sort of delay.

Panama City (PTY) was the most common stop: 49% 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.

Bogotá (BOG) has the shortest average layover time for this route: 1h 33m.

The number of flights available between Chicago and Sao Paulo is 1 per day as of May 2026. The most frequent departure time is 9:00PM, with 100% of daily flights leaving in the evening.

10 flights are operational weekly from Chicago to Sao Paulo as of May 2026. The most popular departure day for this route is Mon, with 20% of flights per week taking off on this day.