$323+ Cheap flights from Chicago (CHI) to Sao Paulo, Brazil (SAO)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAO
Nov 22 — Nov 291
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Sao Paulo with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Sao Paulo are usually found in January or March, booked 10 days in advance, depart on a Sunday or Wednesday and return on a Wednesday
Cheap flight deals from Chicago to Sao Paulo
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Best
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One-way
Cheapest flights from Chicago to Sao PauloExplore the most affordable flight options available from Chicago to Sao Paulo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2026.
Explore the most affordable flight options available from Chicago to Sao Paulo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2026.
This Arajet deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/294:20 am -
1 stop15h 05m
Sat 1/304:13 am -
1 stop21h 07m
Deal found 10/21![Arajet logo]()
$661
This Copa Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:13 pm -
1 stop30h 57m
Thu 11/2611:10 am -
1 stop16h 01m
Deal found 10/19![Copa Airlines logo]()
$666
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:50 pm -
Nonstop10h 25m
Tue 2/29:30 pm -
Nonstop10h 45m
Deal found 10/21![United Airlines logo]()
$670
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/285:50 pm -
Nonstop10h 25m
Wed 2/310:25 pm -
1 stop15h 35m
Deal found 10/21![United Airlines logo]()
$680
This Kissandfly.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:50 pm -
Nonstop10h 25m
Wed 12/99:30 pm -
Nonstop10h 45m
Deal found 10/23![Lufthansa logo]()
$682
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/271:30 pm -
1 stop17h 50m
Mon 2/110:15 pm -
1 stop16h 00m
Deal found 10/21![United Airlines logo]()
$684
This Copa Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:35 am -
1 stop17h 00m
Sun 11/221:40 am -
1 stop25h 31m
Deal found 10/20![Copa Airlines logo]()
$692
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/285:30 am -
1 stop25h 00m
Sat 2/610:15 pm -
1 stop14h 55m
Deal found 10/21![United Airlines logo]()
$693
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:50 pm -
Nonstop10h 25m
Fri 12/119:30 pm -
Nonstop10h 45m
Deal found 10/21![United Airlines logo]()
$703
This CheapOair deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:45 pm -
1 stop19h 55m
Fri 11/139:45 am -
1 stop15h 44m
Deal found 10/20![Azul logo]()
$850
This GOL deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/510:30 pm -
2 stops32h 40m
Sat 12/125:05 am -
2 stops18h 25m
Deal found 10/21![GOL logo]()
$865
This GOL deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:30 pm -
2 stops31h 10m
Mon 12/75:00 am -
2 stops18h 30m
Deal found 10/18![GOL logo]()
$867
Best flights from Chicago to Sao PauloDiscover carefully curated flight deals from Chicago to Sao Paulo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 23, 2026.
Discover carefully curated flight deals from Chicago to Sao Paulo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 23, 2026.
This Copa Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:13 pm -
1 stop27h 37m
Tue 11/2411:10 am -
1 stop16h 01m
Deal found 10/20![Copa Airlines logo]()
$692
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/35:50 pm -
Nonstop10h 25m
Wed 2/109:30 pm -
Nonstop10h 45m
Deal found 10/22![United Airlines logo]()
$779
This GOL deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:30 pm -
2 stops31h 10m
Mon 12/75:00 am -
2 stops18h 30m
Deal found 10/18![GOL logo]()
$867
This FlightHub deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:25 pm -
1 stop21h 50m
Thu 11/129:45 am -
2 stops40h 51m
Deal found 10/23![Multiple Airlines logo]()
$1,370
This CVC Viagens deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CVC Viagens is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/52:17 pm -
2 stops19h 58m
Fri 1/159:45 am -
1 stop15h 29m
Deal found 10/22![Azul logo]()
$1,551
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/315:50 pm -
Nonstop10h 25m
Mon 2/229:30 pm -
Nonstop10h 45m
Deal found 10/22![United Airlines logo]()
$779
This Copa Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/132:13 pm -
1 stop31h 02m
Thu 11/261:40 am -
1 stop14h 06m
Deal found 10/19![Copa Airlines logo]()
$845
This GOL deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/1610:30 pm -
2 stops32h 40m
Thu 1/284:35 am -
2 stops18h 55m
Deal found 10/20![GOL logo]()
$958
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/15:50 pm -
Nonstop10h 25m
Thu 3/119:30 pm -
Nonstop10h 45m
Deal found 10/22![United Airlines logo]()
$910
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/146:50 pm -
Nonstop10h 25m
Sun 3/2110:15 pm -
Nonstop10h 45m
Deal found 10/22![United Airlines logo]()
$910
This GOL deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:51 pm -
2 stops16h 54m
Wed 12/210:50 am -
2 stops36h 40m
Deal found 10/22![GOL logo]()
$1,149
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/171:30 pm -
1 stop17h 50m
Wed 3/109:30 pm -
Nonstop10h 45m
Deal found 10/20![United Airlines logo]()
$994
This United Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:50 pm -
Nonstop10h 25m
Fri 11/279:30 pm -
Nonstop10h 45m
Deal found 10/18![United Airlines logo]()
$1,079
This GOL deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1810:14 am -
2 stops21h 31m
Tue 11/246:00 pm -
2 stops29h 45m
Deal found 10/18![GOL logo]()
$1,370
This GOL deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/262:30 pm -
2 stops18h 15m
Thu 11/1210:35 am -
2 stops36h 55m
Deal found 10/21![GOL logo]()
$1,384
This GOL deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2610:30 pm -
2 stops33h 15m
Sun 1/176:00 pm -
2 stops29h 30m
Deal found 10/19![GOL logo]()
$1,556
This GOL deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1310:30 pm -
2 stops21h 25m
Tue 1/126:00 pm -
2 stops29h 30m
Deal found 10/23![GOL logo]()
$1,556
This GOL deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure GOL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/410:30 pm -
2 stops45h 25m
Sun 1/36:00 pm -
2 stops29h 30m
Deal found 10/20![GOL logo]()
$1,571
Last-minute flights from Chicago to Sao PauloDiscover last-minute flight deals from Chicago to Sao Paulo. Data last updated October 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Sao Paulo. Data last updated October 23, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:25 pm -
1 stop21h 50m
Thu 11/129:45 am -
1 stop15h 44m
Deal found 10/21![Azul logo]()
$887
This Orbitz deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:45 pm -
1 stop21h 45m
Sun 11/19:45 am -
1 stop15h 44m
Deal found 10/19![Azul logo]()
$884
This CheapOair deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:45 pm -
1 stop19h 55m
Fri 11/139:45 am -
1 stop15h 44m
Deal found 10/20![Azul logo]()
$850
This Copa Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:13 pm -
1 stop30h 57m
Thu 11/2611:10 am -
1 stop16h 01m
Deal found 10/19![Copa Airlines logo]()
$666
This Copa Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:35 am -
1 stop17h 00m
Sun 11/221:40 am -
1 stop25h 31m
Deal found 10/20![Copa Airlines logo]()
$692
This Kissandfly.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:50 pm -
Nonstop10h 25m
Wed 12/99:30 pm -
Nonstop10h 45m
Deal found 10/23![Lufthansa logo]()
$682
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:50 pm -
Nonstop10h 25m
Tue 2/29:30 pm -
Nonstop10h 45m
Deal found 10/21![United Airlines logo]()
$670
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/279:00 am -
1 stop22h 20m
Mon 2/19:30 pm -
Nonstop10h 45m
Deal found 10/21![United Airlines logo]()
$674
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:45 am -
1 stop13h 45m
Thu 2/411:25 am -
1 stop14h 15m
Deal found 10/21![Arajet logo]()
$704
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/285:50 pm -
Nonstop10h 25m
Wed 2/310:25 pm -
1 stop15h 35m
Deal found 10/21![United Airlines logo]()
$680
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/285:30 am -
1 stop25h 00m
Sat 2/610:15 pm -
1 stop14h 55m
Deal found 10/21![United Airlines logo]()
$693
This Arajet deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/294:20 am -
1 stop15h 05m
Sat 1/304:13 am -
1 stop21h 07m
Deal found 10/21![Arajet logo]()
$661
One-way flights from Chicago to Sao PauloSearch for one-way flight options from Chicago to Sao Paulo. Find affordable one-way fares based on user searches. Data last updated October 23, 2026.
Search for one-way flight options from Chicago to Sao Paulo. Find affordable one-way fares based on user searches. Data last updated October 23, 2026.
This Arajet deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/294:20 am -
1 stop15h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Arajet logo]()
$323
This Arajet deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/14:20 am -
1 stop15h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Arajet logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/224:20 am -
1 stop15h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Arajet logo]()
$350
This Mytrip deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:45 am -
1 stop13h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Arajet logo]()
$353
This Arajet deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:45 am -
1 stop13h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Arajet logo]()
$358
This Trip.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:20 am -
1 stop15h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Arajet logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:51 am -
3 stops44h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$375
This Booking.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/84:20 am -
1 stop25h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Arajet logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:24 pm -
3 stops36h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$393
This Expedia deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:10 am -
1 stop13h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Arajet logo]()
$396
This Trip.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:35 am -
2 stops20h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$416
This Trip.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/242:13 pm -
2 stops21h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$428
Find flight deals from Chicago to Sao Paulo
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Sao Paulo (SAO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 23, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $626 (Kiwi.com) |
One-way from | $323 (Arajet) |
Popular in | June |
Cheapest in | January |
Average price | $896 |
Good round-trip deal | $1,181 or less |
Good one-way deal | $456 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Sao Paulo that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 23, 2026.
Use the filters below to find and compare flights from Chicago to Sao Paulo that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSao Paulo
ORD Chicago O'Hare Intl - GRU Sao Paulo Guarulhos Intl
ORDGRU
Chicago O'Hare Intl
Sun 11/8
4:20 am-8:40 am
1 stop25h 20m
Sao Paulo Guarulhos Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$401
ChicagoSao Paulo
ORD Chicago O'Hare Intl - VCP Sao Paulo Viracopos
ORDVCP
Chicago O'Hare Intl
Wed 12/2
6:15 pm-6:40 pm
1 stop21h 25m
Sao Paulo Viracopos
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$433
ChicagoSao Paulo
ORD Chicago O'Hare Intl - GRU Sao Paulo Guarulhos Intl
ORDGRU
Chicago O'Hare Intl
Thu 11/26
7:35 am-12:10 am
1 stop13h 35m
Sao Paulo Guarulhos Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$435
ChicagoSao Paulo
ORD Chicago O'Hare Intl - GRU Sao Paulo Guarulhos Intl
ORDGRU
Chicago O'Hare Intl
Wed 11/18
2:13 pm-12:15 am
1 stop31h 02m
Sao Paulo Guarulhos Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$435
ChicagoSao Paulo
ORD Chicago O'Hare Intl - GRU Sao Paulo Guarulhos Intl
ORDGRU
Chicago O'Hare Intl
Tue 11/3
2:13 pm-12:10 am
1 stop30h 57m
Sao Paulo Guarulhos Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$435
ChicagoSao Paulo
ORD Chicago O'Hare Intl - GRU Sao Paulo Guarulhos Intl
ORDGRU
Chicago O'Hare Intl
Sun 11/8
7:35 am-12:15 am
1 stop13h 40m
Sao Paulo Guarulhos Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$460
ChicagoSao Paulo
ORD Chicago O'Hare Intl - GRU Sao Paulo Guarulhos Intl
ORDGRU
Chicago O'Hare Intl
Thu 10/29
8:35 am-12:15 am
1 stop13h 40m
Sao Paulo Guarulhos Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$460
ChicagoSao Paulo
ORD Chicago O'Hare Intl - VCP Sao Paulo Viracopos
ORDVCP
Chicago O'Hare Intl
Wed 12/2
9:13 am-6:40 pm
2 stops30h 27m
Sao Paulo Viracopos
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$466
ChicagoSao Paulo
ORD Chicago O'Hare Intl - GRU Sao Paulo Guarulhos Intl
ORDGRU
Chicago O'Hare Intl
Fri 1/1
5:45 am-10:30 pm
1 stop13h 45m
Sao Paulo Guarulhos Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$472
ChicagoSao Paulo
ORD Chicago O'Hare Intl - VCP Sao Paulo Viracopos
ORDVCP
Chicago O'Hare Intl
Sat 11/28
2:59 pm-6:40 pm
1 stop24h 41m
Sao Paulo Viracopos
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$505
Showing 1-10 of 38 resultsSorted by cheapest first
Compare providers for flights from Chicago to Sao Paulo
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Sao Paulo in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Sao Paulo flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago-Sao Paulo flight deals on Cheapflights vs. Ovago >95% of the time. Price accuracy is based on data collected from Chicago-Sao Paulo flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Sao Paulo flights, Cheapflights users trust Ovago the most. Ovago has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Sao Paulo flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Sao Paulo
Have a flexible travel schedule? Discover the best time to fly to Sao Paulo from Chicago with our price prediction graph.
CHI-SAO
ORD-GRU
ORD-VCP
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Sao Paulo
CHI-SAO
ORD-GRU
ORD-VCP
What is the cheapest month to book a flight from Chicago to Sao Paulo?
Currently, March is the cheapest month in which you can book a flight from Chicago to Sao Paulo (average of $707). Flying from Chicago to Sao Paulo in December is currently the most expensive (average of $1,213). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to SAO?
Find hourly flight availability from Chicago to Sao Paulo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 23, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Sao Paulo as you normally would.
How much does it cost to fly round-trip from Chicago to Sao Paulo?
Airfare is below average for this route at the moment.
Chicago to Sao Paulo flights typically cost between $786 and $1,080 in January.The cheapest round-trip price found within the last 5 days was $626 on Arajet (Jan 31-Feb 13).
What’s the top layover airport for flights from Chicago to Sao Paulo?
Share of 1-stop round-trip flights from Chicago to Sao Paulo chosen by Cheapflights users in the past 12 months, using the same layover each way.
Toronto (YYZ) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to Sao Paulo on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Sao Paulo?
Average round-trip fare for 1-stop flights from Chicago to Sao Paulo, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Panama City (PTY) is the most affordable 1-stop option, with an average round-trip price of $620.
What’s the fastest layover option from Chicago to Sao Paulo?
Shortest average travel time for 1-stop one-way flights from Chicago to Sao Paulo, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Panama City (PTY) have the shortest average one-way travel time for 1-stop routes: 13h 09m.
Which airport typically offers the quickest layover for flights from Chicago to Sao Paulo?
Average layover duration for 1-stop one-way flights from Chicago to Sao Paulo, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Panama City (PTY) offer the fastest connection on this route, with an average layover time of 1h 07m.
How often are flights from Chicago to Sao Paulo delayed?
About 41% of weekly flights between Chicago and Sao Paulo have experienced delays in the past year, with the average delay time being 186 minutes.
What is the most punctual flight time for Chicago to Sao Paulo flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Thursday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Sao Paulo flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 41% of flights being delayed.
How far ahead should I book a flight from Chicago to Sao Paulo?
To ensure you get the cheapest price possible for a flight from Chicago to Sao Paulo, you should look to book at least 9 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Reviews of airlines servicing Sao Paulo
Get insights into the airlines that provide service to Sao Paulo. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Sao Paulo. Reviews last updated October 23, 2026.
Read reviews from past customers who have flown Copa Airlines,LATAM Airlines, andUnited Airlines from Chicago to Sao Paulo. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
7.6
Comfort
7.5
Crew
8.1
Boarding
7.8
Entertainment
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Oct 2026
BOS - PTY
Food
7.0
Overall
7.6
Comfort
7.5
Crew
8.1
Boarding
7.8
Entertainment
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Oct 2026
BOS - PTY
Food
7.0
Overall
7.6
Comfort
7.5
Crew
8.1
Boarding
7.8
Entertainment
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Oct 2026
BOS - PTY
Food
7.0
Overall
7.6
Comfort
7.5
Crew
8.1
Boarding
7.8
Entertainment
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Oct 2026
BOS - PTY
Food
7.0
Overall
7.6
Comfort
7.5
Crew
8.1
Boarding
7.8
Entertainment
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Oct 2026
BOS - PTY
Related info for your journey
Find useful and relevant information for your journey from Chicago to Sao Paulo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Sao Paulo?
Book flights to Sao Paulo if you plan to visit one of these locationsSantos
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Chicago and Sao Paulo flights
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Top 7 airlines flying from Chicago to Sao Paulo
Discover the top 7 airlines that operate flights from Chicago to Sao Paulo. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$212 | Average$1,311 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$272 | Average$537 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$425 | Average$720 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$485 | Average$576 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$596 | Average$620 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$607 | Average$981 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$765 | Average$1,076 | FlexibilityNo cancel fee | On-time69% |