Cheap Flights from Sao Paulo to Chicago from $274

Frequently Asked Questions

• What are the cheapest flights from Sao Paulo to Chicago (SAO-CHI)?

  Based on Trip.com data, DM Airlines offers one-way fares as low as $274 on Cheapest nonstop routes (e.g. GRU to ORD on Tue, May 26), while Gol Linhas Aereas Inteligentes offers Cheapest nonstop round-trips from $587 departing on Mon, Apr 27 and returning on Mon, May 4.

• Which airlines offer direct flights from Sao Paulo to Chicago?

  At the moment, you can catch a nonstop flight from Sao Paulo to Chicago with the following airlines, including: avianca Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• How long does it take to fly from Sao Paulo (SAO) to Chicago (CHI) and what is the distance?

  It takes around 10 hours 35 minutes to fly from Sao Paulo (SAO) to Chicago (CHI).

• When is the best time to book flights from Sao Paulo to Chicago?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Sao Paulo to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

• How can I find the best deals on flights from Sao Paulo to Chicago?

  To find best deals on flights from Sao Paulo to Chicago, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Tue, May 26, with one-way flights priced at just $274.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is United Airlines.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around January.
  · Get exclusive promo codes for Trip.com app users.

• When are flight tickets from Sao Paulo (SAO) to Chicago (CHI) the cheapest?

  The cheapest months to fly from Sao Paulo to Chicago is November, when demand for travel is lower.

• Which upcoming date is cheapest to fly from Sao Paulo to Chicago on?

  After crunching the numbers on our April flight calendar, it's currently cheapest to fly from Sao Paulo to Chicago on April 26, 2026 with Arajet Airline, with prices starting at $245.

• Which airports can I fly to for Chicago from Sao Paulo?

  You can land at any one of the following hubs in Chicago, with São Paulo/Guarulhos–Governor André Franco Montoro International Airport to Chicago O'Hare International Airport (GRU-ORD) is by far the most common option on this route: Chicago O'Hare International Airport (ORD) Chicago Midway International Airport (MDW) Chicago Rockford International Airport (RFD).

• Is there any time difference between Sao Paulo and Chicago?

  The time difference between Chicago and Sao Paulo is 3h.

• How do I change or cancel my ticket from Sao Paulo to Chicago?

  Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.