Cheap flights from Sao Paulo to Chicago from $248

The month of February is, on average, the cheapest month to fly to Chicago from Sao Paulo, with most prices found around $768. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from Sao Paulo to Chicago during April average around $772.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $873. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Sao Paulo to Chicago for around $1,254.

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 $926 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 $722 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.

As of October 2026, prices for Sao Paulo to Chicago flights are approximately 5% cheaper when compared to flights at the same time last year.

Historically, on average around 13% 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 189 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.

Sunday 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 13% of their flights experiencing any sort of delay.

Montreal (YUL) was the most common stop: 41% of momondo users choosing 1-stop flights on this route connected there.

Flights via Montreal (YUL) offer the lowest average round-trip price of $580.

Flights connecting via Bogotá (BOG) have the shortest average one-way travel time: 13h 30m.

Panama City (PTY) has the shortest average layover time for this route: 1h 05m.

As of October 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 October 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.