Cheap flights from Sao Paulo Guarulhos Intl Airport to Chicago from $256

The month of February is, on average, the cheapest month to fly to Chicago from Sao Paulo Guarulhos Intl Airport, with most prices found around $718. If you’re not able to fly to Chicago in February, then November is your next best option. Flight prices from Sao Paulo Guarulhos Intl Airport to Chicago during November average around $733.

The cheapest day to depart on your flight to Chicago is on a Sunday when prices can be found for as low as $827. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Sao Paulo Guarulhos Intl Airport to Chicago for around $988.

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

You are more likely to see cheaper flights to Chicago from Sao Paulo Guarulhos Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $864 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Sao Paulo Guarulhos Intl Airport for as low as $757 on momondo.

There are 3 cabin classes available to choose from on Sao Paulo Guarulhos Intl to Chicago 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 85% on your flight if you consider stops on a Sao Paulo Guarulhos Intl Airport to Chicago flight.

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

United Airlines, Avianca and Copa Airlines are the top three most popular airlines that fly to Chicago from Sao Paulo Guarulhos Intl Airport according to our data. United Airlines is the first choice among our users, with 66% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 12% of flights between Sao Paulo and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 178 minutes.

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

Monday is statistically the day of the week which experiences the fewest number of delays on this flight route. Thursday 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 12% of their flights experiencing any sort of delay.

Panama City (PTY) was the most common stop: 42% 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 $495.

Flights connecting via Punta Cana (PUJ) have the shortest average one-way travel time: 13h 17m.

Panama City (PTY) has the shortest average layover time for this route: 1h 13m.

The number of flights available between Sao Paulo Guarulhos Intl Airport and Chicago is 2 per day as of March 2026. The most frequent departure time is 10:00PM, with 100% of daily flights leaving in the evening.

As of March 2026, there are 14 flights per week flying from Sao Paulo Guarulhos Intl Airport to Chicago. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.