Cheap flights from Sao Paulo to Chicago

São Paulo
SAO
Chicago FSS
CHI

Flight deals from Sao Paulo to Chicago

Below you can see the best deals on flights Sao Paulo — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 27 September, from $277.

Top 10 cheap flights from Sao Paulo to Chicago

DM
DM
F9
$ 312

Sao Paulo — Chicago

06:35—15:20
21 Sep 2026
34 h 45 m
2 stops
DM
DM
F9
$ 332

Sao Paulo — Chicago

03:50—14:45
16 Sep 2026
36 h 55 m
2 stops
DM
DM
AA
AA
AA
$ 349

Sao Paulo — Chicago

03:50—15:05
9 Sep 2026
37 h 15 m
4 stops
DM
DM
AA
AA
AA
$ 349

Sao Paulo — Chicago

03:50—16:00
9 Sep 2026
38 h 10 m
4 stops
DM
DM
AA
AA
AA
$ 349

Sao Paulo — Chicago

03:50—16:46
9 Sep 2026
38 h 56 m
4 stops
DM
DM
AA
AA
AA
$ 349

Sao Paulo — Chicago

03:50—17:28
9 Sep 2026
39 h 38 m
4 stops
DM
DM
AA
AA
AA
$ 349

Sao Paulo — Chicago

03:50—17:44
9 Sep 2026
39 h 54 m
4 stops
DM
DM
F9
F9
$ 352

Sao Paulo — Chicago

06:35—11:51
21 Sep 2026
31 h 16 m
3 stops
DM
DM
UA
$ 370

Sao Paulo — Chicago

06:35—09:29
21 Sep 2026
28 h 54 m
2 stops
DM
DM
UA
$ 370

Sao Paulo — Chicago

06:35—14:55
21 Sep 2026
34 h 20 m
2 stops

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Sao Paulo — Chicago flight

Looking for cheap flights from Sao Paulo to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your Sao Paulo — Chicago ticket online at the best price.

The route has direct flights — around 14 flights per week, flights are operated by United Airlines, a nonstop flight takes about 10 h 25 min, the distance between the cities is around 8,384 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $277Min. price
SeptemberCheapest
AugustPeak season
YesDirect flights
8,384 kmDistance
10 h 25 minTravel time
1Airlines
14 / wkFlights

Flight schedule from Sao Paulo to Chicago

The table shows direct flights from Sao Paulo to Chicago on the selected date. The flight takes approximately 10 h 25 min. Regular flights are operated by United Airlines. Departures from Sao Paulo-Guarulhos International Airport, Sao Paulo/Congonhas Airport and Viracopos Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 26 Aug 2026

Flight ticket prices by day: Sao Paulo — Chicago

Below is a calendar of the lowest flight ticket prices for Sao Paulo — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $277 in September, and the most expensive are around $460 in August. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Average one-way fares from Sao Paulo to Chicago by month. Tickets are usually cheapest in April (around $342) and priciest in August (about $501) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$410highMay$342lowSep$387medium
Feb$387mediumJun$387mediumOct$365low
Mar$376mediumJul$479highNov$353low
Apr$342lowAug$501highDec$422high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in September and most expensive in August. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a Sao Paulo — Chicago ticket

  • Book ahead: fares for Sao Paulo — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Sao Paulo is served by more than one airport — compare fares and travel time to each before you book.
  • The cheapest month to fly to Chicago is usually September — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Sao Paulo — Chicago route are operated by 1 airline; United Airlines runs the most flights (around 100% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    5x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight GRU → ORD5x/week
      Duration
      10h 25m
      Days
      MTWTFSS
    100.0%Open →

Cities and airports on the Sao Paulo — Chicago route

Flights Sao Paulo — Chicago depart from Sao Paulo-Guarulhos International Airport, Sao Paulo/Congonhas Airport and Viracopos Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Sao Paulo

SAO
Brazil
About the cityHow to get thereWeatherAll about the country Brazil
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Sao Paulo — Chicago flight

How long is the flight from Sao Paulo to Chicago?

A nonstop Sao Paulo — Chicago flight takes about 10 h 25 min — the distance between the cities is around 8,384 km.

How far is it from Sao Paulo to Chicago?

The distance from Sao Paulo to Chicago is about 8,384 km, which a nonstop flight covers in around 10 h 25 min.

Are there direct flights from Sao Paulo to Chicago?

Yes, there are nonstop flights Sao Paulo — Chicago — around 14 flights per week.

Which airlines fly from Sao Paulo to Chicago?

Airlines operating Sao Paulo — Chicago include United Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Sao Paulo — Chicago flights use?

Flights from Sao Paulo depart from Sao Paulo-Guarulhos International Airport, Sao Paulo/Congonhas Airport, Viracopos Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Sao Paulo to Chicago?

The price of a Sao Paulo — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in August. Tickets typically cost between $277 and $460. Check the current lowest fare and low-price calendar on this page.

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

Flights Sao Paulo — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Sao Paulo to Chicago?

To catch a low fare Sao Paulo — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

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