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Cheap flight deals from Sao Paulo to Chicago Starting at $597

For as little as $597, you can take your next adventure to Chicago without breaking the bank. Choose between one-way and return tickets from Sao Paulo below.

  • One way
  • Round-trip
      • Cheapest nonstop
        GRU21:45
        10h 40m
        Nonstop
        ORD05:25
        Sat, Nov 30|Sao Paulo - Chicago|United Airlines
        $597$747
        20% OFF
        20% OFF
        $747$597

        Choose United Airlines flights from Sao Paulo to Chicago. The one-way direct flight with United Airlines departs from São Paulo/Guarulhos International Airport on Sat, Nov 30, arriving at O'Hare International Airport. One-way Prices start from $597 including taxes and charges.

      • GRU21:45
        10h 40m
        Nonstop
        ORD05:25
        Wed, Dec 25|Sao Paulo - Chicago|United Airlines
        $665$747
        11% OFF
        11% OFF
        $747$665

        Choose United Airlines flights from Sao Paulo to Chicago. The one-way direct flight with United Airlines departs from São Paulo/Guarulhos International Airport on Wed, Dec 25, arriving at O'Hare International Airport. One-way Prices start from $665 including taxes and charges.

      • GRU21:35
        25h 30m
        1 stop
        ORD20:05
        Mon, Nov 25|Sao Paulo - Chicago|Arajet Airline
        $263$747
        65% OFF
        65% OFF
        $747$263

        Choose Arajet Airline flights from Sao Paulo to Chicago. The one-way connecting flight with Arajet Airline departs from São Paulo/Guarulhos International Airport on Mon, Nov 25, arriving at O'Hare International Airport. One-way Prices start from $263 including taxes and charges.

      • GRU05:25
        18h 6m
        1 stop
        ORD20:31
        Fri, Dec 13|Sao Paulo - Chicago|Arajet Airline
        $307
        $307

        Choose Arajet Airline flights from Sao Paulo to Chicago. The one-way connecting flight with Arajet Airline departs from São Paulo/Guarulhos International Airport on Fri, Dec 13, arriving at O'Hare International Airport. One-way Prices start from $307 including taxes and charges.

      • GRU23:10
        21h 25m
        1 stop
        MDW17:35
        Mon, Nov 25|Sao Paulo - Chicago|LATAM Airlines
        $309
        $309

        Choose LATAM Airlines flights from Sao Paulo to Chicago. The one-way connecting flight with LATAM Airlines departs from São Paulo/Guarulhos International Airport on Mon, Nov 25, arriving at Midway International Airport. One-way Prices start from $309 including taxes and charges.

      • GRU23:10
        15h 59m
        1 stop
        ORD12:09
        Tue, Dec 10|Sao Paulo - Chicago|LATAM Airlines
        $353
        $353

        Choose LATAM Airlines flights from Sao Paulo to Chicago. The one-way connecting flight with LATAM Airlines departs from São Paulo/Guarulhos International Airport on Tue, Dec 10, arriving at O'Hare International Airport. One-way Prices start from $353 including taxes and charges.

      • GRU23:10
        15h 59m
        1 stop
        ORD12:09
        Mon, Dec 9|Sao Paulo - Chicago|LATAM Airlines
        $353
        $353

        Choose LATAM Airlines flights from Sao Paulo to Chicago. The one-way connecting flight with LATAM Airlines departs from São Paulo/Guarulhos International Airport on Mon, Dec 9, arriving at O'Hare International Airport. One-way Prices start from $353 including taxes and charges.

      • GRU21:35
        27h 32m
        1 stop
        ORD22:07
        Wed, Dec 4|Sao Paulo - Chicago|Arajet Airline
        $364
        $364

        Choose Arajet Airline flights from Sao Paulo to Chicago. The one-way connecting flight with Arajet Airline departs from São Paulo/Guarulhos International Airport on Wed, Dec 4, arriving at O'Hare International Airport. One-way Prices start from $364 including taxes and charges.

      • GRU10:50
        31h 23m
        1 stop
        MDW15:13
        Wed, Jan 29|Sao Paulo - Chicago|LATAM Airlines
        $364
        $364

        Choose LATAM Airlines flights from Sao Paulo to Chicago. The one-way connecting flight with LATAM Airlines departs from São Paulo/Guarulhos International Airport on Wed, Jan 29, arriving at Midway International Airport. One-way Prices start from $364 including taxes and charges.

      • GRU10:50
        31h 23m
        1 stop
        MDW15:13
        Wed, Feb 19|Sao Paulo - Chicago|LATAM Airlines
        $370
        $370

        Choose LATAM Airlines flights from Sao Paulo to Chicago. The one-way connecting flight with LATAM Airlines departs from São Paulo/Guarulhos International Airport on Wed, Feb 19, arriving at Midway International Airport. One-way Prices start from $370 including taxes and charges.

      • SAO13:00
        3h 5m
        Nonstop
        CHI14:00
        Mon, Dec 2|Sao Paulo - Chicago|United Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly from Sao Paulo to Chicago?

Price trend charts are a great way of tracking how much your flights cost in the lead up to departure and can help you choose when to book your tickets. See how prices to Chicago from Sao Paulo have changed and are set to move below.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find cheap airlines flights from Sao Paulo to Chicago

We have a range of prices from different airlines providing flights from Sao Paulo to Chicago. Check below for the journey which best suits your travel needs.

Arajet Airline
From $263
Copa Airlines
From $264
avianca
From $265
Sky Airline
From $298
Gol Linhas Aereas Inteligentes
From $302
Azul
From $306
LATAM Airlines
From $309
United Airlines
From $374
Aeromexico
From $417
American Airlines
From $477

Find more flights and airlines

Alternative Cheap Routes from Sao Paulo to Chicago

Did you know that you can save money and time on an alternative route from Sao Paulo to Chicago? Check out some of the different available routes below.

  • Cheapest
    DM Airlines
    GRU
    21:35
    25h 30m
    1 transfer
    ORD
    20:05
    São Paulo/Guarulhos International Airport - O'Hare International Airport
    Mon, Nov 25DM Airlines
    $263
  • Gol Linhas Aereas Inteligentes
    VCP
    09:40
    29h 35m
    2 transfer
    ORD
    12:15
    Viracopos International Airport - O'Hare International Airport
    Sun, Feb 2Gol Linhas Aereas Inteligentes
    $302
  • LATAM Airlines
    GRU
    23:10
    21h 25m
    1 transfer
    MDW
    17:35
    São Paulo/Guarulhos International Airport - Midway International Airport
    Mon, Nov 25LATAM Airlines
    $309
  • LATAM Airlines
    GRU
    23:10
    21h 25m
    1 transfer
    MDW
    17:35
    São Paulo/Guarulhos International Airport - Midway International Airport
    Mon, Nov 25LATAM Airlines
    $309
    Find More Flights

Frequently Asked Questions

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

    Airlines adjust prices for flights from Sao Paulo to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Sao Paulo (SAO) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around $1,421.

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

    It takes around 10 hours 32 minutes to fly from Sao Paulo (SAO) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

  • What are the most popular airlines that fly from Sao Paulo (SAO) to Chicago (CHI)?

    Airlines with flights from Sao Paulo (SAO) to Chicago (CHI): United Airlines and All Nippon Airways.

How to find a cheap flight from Sao Paulo to Chicago

If you don’t know some of the key things to look out for when buying flight tickets, prices can often end up sky high or, worse, sold out! We’ve carefully compiled our six most important steps to help ensure you’re getting the best deals when planning your next journey.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Info | Sao Paulo to Chicago

Cheapest nonstop flight price$262
Cheapest round-trip ticket price$891
Off-season for travelOctober
Peak season for travelAugust
Flight distance8,406.99 km
Average flight time10 hours 32 minutes
Popular airlineAir Canada

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