Cheap flights from Sao Paulo to Chicago from $261

The month of May is, on average, the cheapest month to fly to Chicago from Sao Paulo, with most prices found around $124. If you’re not able to fly to Chicago in May, then June is your next best option. Flight prices from Sao Paulo to Chicago during June average around $145.

The cheapest day to depart on your flight to Chicago is on a Sunday when prices can be found for as low as $828. This is often the case because there is less demand to fly during this day of the week. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Sao Paulo to Chicago for around $1,038.

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

You are more likely to see cheaper flights to Chicago from Sao Paulo 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 for as low as $768 on momondo.

There are 3 cabin classes available to choose from on Sao Paulo 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 80% on your flight if you consider stops on a Sao Paulo to Chicago flight.

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

United Airlines, Avianca and Copa Airlines are the top three most popular airlines that fly to Chicago from Sao Paulo according to our data. United Airlines is the first choice among our users, with 70% 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 187 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.

As of May 2026, 2 flights take off from Sao Paulo and land in Chicago each day. The most common flight departure time for this route is 10:00PM, with 100% of daily flights taking off in the evening.

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