$279+ Cheap flights from Chicago (CHI) to Sao Paulo, Brazil (SAO)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAO
Sep 23 — Sep 301
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 76 days in advance, depart on a Wednesday or Monday and return on a Wednesday
Cheap flight deals from Chicago to Sao Paulo
Cheapest
Best
Last-minute
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 August 24, 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 August 24, 2026.
This Booking.com deal was found by Cheapflights users on 8/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:30 am -
1 stop14h 55m
Thu 10/111:50 am -
1 stop13h 50m
Deal found 8/21![Arajet logo]()
$508
This Arajet deal was found by Cheapflights users on 8/22. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:12 pm -
1 stop12h 56m
Thu 10/111:50 am -
1 stop13h 50m
Deal found 8/22![Arajet logo]()
$547
This Booking.com deal was found by Cheapflights users on 8/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:45 am -
1 stop13h 45m
Thu 10/111:50 am -
1 stop13h 50m
Deal found 8/21![Arajet logo]()
$550
This Expedia deal was found by Cheapflights users on 8/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/293:20 am -
1 stop16h 05m
Thu 12/311:25 am -
1 stop14h 15m
Deal found 8/20![Arajet logo]()
$568
This Arajet deal was found by Cheapflights users on 8/22. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:45 am -
1 stop13h 45m
Thu 10/111:50 am -
1 stop13h 50m
Deal found 8/22![Arajet logo]()
$577
This Booking.com deal was found by Cheapflights users on 8/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1712:12 pm -
1 stop12h 56m
Sun 10/254:05 am -
1 stop20h 05m
Deal found 8/23![Arajet logo]()
$580
This Arajet deal was found by Cheapflights users on 8/20. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:27 am -
1 stop13h 15m
Fri 11/1310:38 pm -
1 stop13h 19m
Deal found 8/20![Arajet logo]()
$587
This Expedia deal was found by Cheapflights users on 8/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:45 am -
1 stop13h 45m
Fri 10/3010:37 pm -
1 stop13h 20m
Deal found 8/23![Arajet logo]()
$591
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:30 am -
1 stop14h 55m
Thu 10/1511:50 am -
1 stop13h 50m
Deal found 8/19![Arajet logo]()
$594
This eDestinos deal was found by Cheapflights users on 8/22. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:30 am -
1 stop14h 55m
Wed 10/211:00 am -
1 stop24h 40m
Deal found 8/22![Arajet logo]()
$595
This FlightHub deal was found by Cheapflights users on 8/23. 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.
Wed 10/285:09 pm -
1 stop14h 26m
Tue 11/38:20 pm -
2 stops53h 13m
Deal found 8/23![LATAM Airlines logo]()
$754
This Justfly.com deal was found by Cheapflights users on 8/20. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/302:51 pm -
2 stops17h 49m
Thu 12/36:05 am -
2 stops18h 31m
Deal found 8/20![GOL logo]()
$775
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 August 24, 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 August 24, 2026.
This Arajet deal was found by Cheapflights users on 8/20. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/63:20 am -
1 stop16h 05m
Thu 1/2111:25 am -
1 stop14h 15m
Deal found 8/20![Arajet logo]()
$784
This GOL deal was found by Cheapflights users on 8/20. 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.
Sun 11/12:38 pm -
2 stops17h 02m
Fri 11/136:05 am -
2 stops18h 50m
Deal found 8/20![GOL logo]()
$947
This Trip.com deal was found by Cheapflights users on 8/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/811:50 am -
2 stops28h 05m
Wed 9/3011:55 pm -
2 stops25h 49m
Deal found 8/22![Multiple Airlines logo]()
$973
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Mon 10/199:30 pm -
Nonstop10h 10m
Wed 10/2810:15 pm -
Nonstop10h 45m
Deal found 8/20![United Airlines logo]()
$1,219
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:04 am -
1 stop21h 36m
Mon 10/269:30 pm -
1 stop16h 24m
Deal found 8/21![Delta logo]()
$1,233
This GOL deal was found by Cheapflights users on 8/22. 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.
Mon 10/122:30 pm -
2 stops18h 45m
Thu 10/226:30 am -
2 stops17h 25m
Deal found 8/22![GOL logo]()
$999
This GOL deal was found by Cheapflights users on 8/19. 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.
Fri 11/68:15 am -
2 stops23h 05m
Thu 11/126:00 pm -
2 stops30h 31m
Deal found 8/19![GOL logo]()
$1,007
This Ovago deal was found by Cheapflights users on 8/19. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am -
1 stop32h 55m
Sun 9/1310:30 pm -
1 stop17h 15m
Deal found 8/19![Multiple Airlines logo]()
$1,198
This GOL deal was found by Cheapflights users on 8/22. 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.
Sun 10/1811:20 pm -
2 stops33h 55m
Sat 10/243:55 pm -
2 stops33h 38m
Deal found 8/22![GOL logo]()
$1,012
This Delta deal was found by Cheapflights users on 8/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:59 am -
1 stop16h 41m
Mon 11/27:30 am -
2 stops18h 03m
Deal found 8/22![Delta logo]()
$1,234
This United Airlines deal was found by Cheapflights users on 8/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/129:30 pm -
Nonstop10h 10m
Fri 10/2310:20 pm -
Nonstop10h 25m
Deal found 8/23![United Airlines logo]()
$1,259
This Delta deal was found by Cheapflights users on 8/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:09 pm -
1 stop13h 26m
Wed 12/29:30 pm -
1 stop16h 03m
Deal found 8/20![Delta logo]()
$1,234
This Mytrip deal was found by Cheapflights users on 8/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/611:20 pm -
2 stops21h 00m
Sun 10/117:40 pm -
2 stops27h 40m
Deal found 8/19![GOL logo]()
$1,039
This United Airlines deal was found by Cheapflights users on 8/22. 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 10/145:30 am -
1 stop23h 00m
Sat 10/2410:20 pm -
Nonstop10h 25m
Deal found 8/22![United Airlines logo]()
$1,263
This Delta deal was found by Cheapflights users on 8/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:49 pm -
1 stop14h 51m
Wed 10/289:30 pm -
1 stop20h 44m
Deal found 8/20![Delta logo]()
$1,234
This United Airlines deal was found by Cheapflights users on 8/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/88:50 am -
1 stop22h 40m
Sat 10/1710:20 pm -
Nonstop10h 25m
Deal found 8/19![United Airlines logo]()
$1,263
This GOL deal was found by Cheapflights users on 8/20. 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.
Mon 12/72:38 pm -
2 stops18h 02m
Thu 1/213:55 pm -
2 stops31h 25m
Deal found 8/20![GOL logo]()
$1,044
This Delta deal was found by Cheapflights users on 8/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:04 am -
1 stop21h 36m
Mon 10/269:30 pm -
1 stop16h 24m
Deal found 8/20![Delta logo]()
$1,274
This United Airlines deal was found by Cheapflights users on 8/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:30 pm -
Nonstop10h 05m
Sat 10/1710:20 pm -
Nonstop10h 25m
Deal found 8/19![United Airlines logo]()
$1,299
This GOL deal was found by Cheapflights users on 8/22. 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.
Mon 10/122:30 pm -
2 stops20h 40m
Fri 10/231:55 pm -
2 stops36h 43m
Deal found 8/22![GOL logo]()
$1,086
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Sat 11/211:29 pm -
2 stops18h 41m
Sat 11/289:45 am -
1 stop29h 39m
Deal found 8/21![Multiple Airlines logo]()
$1,646
This Delta deal was found by Cheapflights users on 8/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:04 am -
1 stop21h 36m
Tue 10/279:30 pm -
1 stop16h 24m
Deal found 8/20![Delta logo]()
$1,274
This United Airlines deal was found by Cheapflights users on 8/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:29 am -
1 stop23h 01m
Sat 11/289:30 pm -
Nonstop10h 45m
Deal found 8/23![United Airlines logo]()
$1,303
This GOL deal was found by Cheapflights users on 8/23. 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.
Mon 10/122:30 pm -
2 stops18h 15m
Thu 10/226:00 pm -
2 stops29h 30m
Deal found 8/23![GOL logo]()
$1,087
This Delta deal was found by Cheapflights users on 8/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:35 pm -
1 stop14h 10m
Sat 11/2810:15 am -
2 stops16h 39m
Deal found 8/23![Delta logo]()
$1,278
This GOL deal was found by Cheapflights users on 8/22. 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.
Sun 10/1811:20 pm -
2 stops17h 30m
Sun 10/256:05 am -
2 stops19h 28m
Deal found 8/22![GOL logo]()
$1,104
This United Airlines deal was found by Cheapflights users on 8/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/74:00 pm -
1 stop13h 10m
Thu 10/1510:20 pm -
Nonstop10h 25m
Deal found 8/19![United Airlines logo]()
$1,373
This Delta deal was found by Cheapflights users on 8/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:29 am -
2 stops18h 11m
Mon 11/211:45 pm -
1 stop13h 58m
Deal found 8/19![Delta logo]()
$1,278
This Mytrip deal was found by Cheapflights users on 8/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1211:20 pm -
2 stops17h 30m
Mon 10/266:45 pm -
2 stops28h 35m
Deal found 8/20![GOL logo]()
$1,110
This Delta deal was found by Cheapflights users on 8/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:04 am -
1 stop21h 36m
Fri 10/2311:00 pm -
2 stops18h 17m
Deal found 8/22![Delta logo]()
$1,278
Last-minute flights from Chicago to Sao PauloDiscover last-minute flight deals from Chicago to Sao Paulo. Data last updated August 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Sao Paulo. Data last updated August 24, 2026 and is based on user searches.
This Arajet deal was found by Cheapflights users on 8/22. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:45 am -
1 stop13h 45m
Thu 10/111:50 am -
1 stop13h 50m
Deal found 8/22![Arajet logo]()
$577
This Booking.com deal was found by Cheapflights users on 8/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:45 am -
1 stop13h 45m
Sun 9/204:08 am -
1 stop20h 02m
Deal found 8/23![Arajet logo]()
$610
This Arajet deal was found by Cheapflights users on 8/22. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:12 pm -
1 stop12h 56m
Thu 10/111:50 am -
1 stop13h 50m
Deal found 8/22![Arajet logo]()
$547
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm -
2 stops35h 45m
Thu 10/111:50 am -
1 stop13h 50m
Deal found 8/22![Multiple Airlines logo]()
$628
This Arajet deal was found by Cheapflights users on 8/22. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:12 pm -
1 stop12h 56m
Fri 10/211:55 pm -
1 stop13h 17m
Deal found 8/22![Arajet logo]()
$630
This Arajet deal was found by Cheapflights users on 8/22. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:12 pm -
1 stop12h 56m
Sun 10/44:08 am -
1 stop20h 02m
Deal found 8/22![Arajet logo]()
$631
This Booking.com deal was found by Cheapflights users on 8/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:30 am -
1 stop14h 55m
Thu 10/111:50 am -
1 stop13h 50m
Deal found 8/21![Arajet logo]()
$508
This Arajet deal was found by Cheapflights users on 8/22. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:30 am -
1 stop14h 55m
Sun 10/44:08 am -
1 stop20h 02m
Deal found 8/22![Arajet logo]()
$611
This Booking.com deal was found by Cheapflights users on 8/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:45 am -
1 stop13h 45m
Fri 9/2511:55 pm -
1 stop13h 17m
Deal found 8/19![Arajet logo]()
$639
This Trip.com deal was found by Cheapflights users on 8/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:11 am -
1 stop32h 44m
Sun 9/2710:30 pm -
2 stops25h 09m
Deal found 8/19![Multiple Airlines logo]()
$823
This Booking.com deal was found by Cheapflights users on 8/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:45 am -
1 stop13h 45m
Thu 10/111:50 am -
1 stop13h 50m
Deal found 8/21![Arajet logo]()
$550
This Arajet deal was found by Cheapflights users on 8/19. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:45 am -
1 stop13h 45m
Fri 10/211:55 pm -
1 stop13h 17m
Deal found 8/19![Arajet logo]()
$637
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 August 24, 2026.
Search for one-way flight options from Chicago to Sao Paulo. Find affordable one-way fares based on user searches. Data last updated August 24, 2026.
This Expedia deal was found by Cheapflights users on 8/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/63:20 am -
1 stop16h 05m
Deal found 8/21![Arajet logo]()
$279
This Mytrip deal was found by Cheapflights users on 8/24. 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.
Sat 11/1410:27 am -
1 stop13h 15m
Deal found 8/24![Arajet logo]()
$282
This CheapOair deal was found by Cheapflights users on 8/24. 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.
Sun 11/293:20 am -
1 stop16h 05m
Deal found 8/24![Arajet logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:45 am -
1 stop13h 45m
Deal found 8/22![Arajet logo]()
$302
This Booking.com deal was found by Cheapflights users on 8/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:12 pm -
1 stop12h 56m
Deal found 8/22![Arajet logo]()
$309
This Arajet deal was found by Cheapflights users on 8/23. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:30 am -
1 stop14h 55m
Deal found 8/23![Arajet logo]()
$313
This CheapOair deal was found by Cheapflights users on 8/24. 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.
Mon 9/285:30 am -
1 stop14h 55m
Deal found 8/24![Arajet logo]()
$315
This Mytrip deal was found by Cheapflights users on 8/24. 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.
Sun 11/153:20 am -
1 stop26h 07m
Deal found 8/24![Arajet logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/157:11 am -
1 stop32h 44m
Deal found 8/23![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:12 pm -
1 stop12h 56m
Deal found 8/22![Arajet logo]()
$337
This Booking.com deal was found by Cheapflights users on 8/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3111:27 am -
1 stop13h 15m
Deal found 8/21![Arajet logo]()
$340
This Expedia deal was found by Cheapflights users on 8/24. 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 2/2010:27 am -
1 stop13h 46m
Deal found 8/24![Arajet logo]()
$342
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 August 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $508 (Booking.com) |
One-way from | $279 (Expedia) |
Popular in | June |
Cheapest in | January |
Average price | $792 |
Good round-trip deal | $1,090 or less |
Good one-way deal | $426 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 August 24, 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 12/6
3:20 am-10:25 pm
1 stop16h 05m
Sao Paulo Guarulhos Intl
Thu 1/21
11:25 am-10:40 pm
1 stop14h 15m
$784
ChicagoSao Paulo
ORD Chicago O'Hare Intl - CGH Sao Paulo Congonhas
ORDCGH
Chicago O'Hare Intl
Sun 11/1
2:38 pm-10:40 am
2 stops17h 02m
Sao Paulo Congonhas
Fri 11/13
6:05 am-9:55 pm
2 stops18h 50m
$947
ChicagoSao Paulo
MDW Chicago Midway - VCP Sao Paulo Viracopos
MDWVCP
Chicago Midway
Tue 9/8
11:50 am-5:55 pm
2 stops28h 05m
Sao Paulo Viracopos
Wed 9/30
11:55 pm-11:44 pm
2 stops25h 49m
$973
ChicagoSao Paulo
ORD Chicago O'Hare Intl - CGH Sao Paulo Congonhas
ORDCGH
Chicago O'Hare Intl
Mon 10/12
2:30 pm-11:15 am
2 stops18h 45m
Sao Paulo Congonhas
Thu 10/22
6:30 am-9:55 pm
2 stops17h 25m
$999
ChicagoSao Paulo
ORD Chicago O'Hare Intl - VCP Sao Paulo Viracopos
ORDVCP
Chicago O'Hare Intl
Fri 11/6
8:15 am-10:20 am
2 stops23h 05m
Sao Paulo Viracopos
Thu 11/12
6:00 pm-9:31 pm
2 stops30h 31m
$1,007
ChicagoSao Paulo
ORD Chicago O'Hare Intl - CGH Sao Paulo Congonhas
ORDCGH
Chicago O'Hare Intl
Sun 10/18
11:20 pm-11:15 am
2 stops33h 55m
Sao Paulo Congonhas
Sat 10/24
3:55 pm-11:33 pm
2 stops33h 38m
$1,012
ChicagoSao Paulo
ORD Chicago O'Hare Intl - CGH Sao Paulo Congonhas
ORDCGH
Chicago O'Hare Intl
Tue 10/6
11:20 pm-10:20 pm
2 stops21h 00m
Sao Paulo Congonhas
Sun 10/11
7:40 pm-9:20 pm
2 stops27h 40m
$1,039
ChicagoSao Paulo
ORD Chicago O'Hare Intl - CGH Sao Paulo Congonhas
ORDCGH
Chicago O'Hare Intl
Mon 12/7
2:38 pm-11:40 am
2 stops18h 02m
Sao Paulo Congonhas
Thu 1/21
3:55 pm-8:20 pm
2 stops31h 25m
$1,044
ChicagoSao Paulo
ORD Chicago O'Hare Intl - GRU Sao Paulo Guarulhos Intl
ORDGRU
Chicago O'Hare Intl
Mon 10/12
2:30 pm-1:10 pm
2 stops20h 40m
Sao Paulo Guarulhos Intl
Fri 10/23
1:55 pm-12:38 am
2 stops36h 43m
$1,086
ChicagoSao Paulo
ORD Chicago O'Hare Intl - VCP Sao Paulo Viracopos
ORDVCP
Chicago O'Hare Intl
Mon 10/12
2:30 pm-10:45 am
2 stops18h 15m
Sao Paulo Viracopos
Thu 10/22
6:00 pm-9:30 pm
2 stops29h 30m
$1,087
Showing 1-10 of 60 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 August.
| 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 |
- Most accurate provider: When it comes to deals on Chicago-Sao Paulo flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Sao Paulo flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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
MDW-GRU
ORD-CGH
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
MDW-GRU
ORD-CGH
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 $700). Flying from Chicago to Sao Paulo in December is currently the most expensive (average of $1,144). 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 August 24, 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 $706 and $917 in September.The cheapest round-trip price found within the last 5 days was $508 on Arajet (Sep 14-Oct 1).
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 44% of weekly flights between Chicago and Sao Paulo have experienced delays in the past year, with the average delay time being 187 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 Wednesday 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 43% 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 August 24, 2026.
Read reviews from past customers who have flown Copa Airlines,United Airlines, andAir Canada 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.
Overall
7.6
Boarding
7.8
Crew
8.1
Entertainment
6.8
Food
6.9
Comfort
7.4
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Overall
7.6
Boarding
7.8
Crew
8.1
Entertainment
6.8
Food
6.9
Comfort
7.4
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Overall
7.6
Boarding
7.8
Crew
8.1
Entertainment
6.8
Food
6.9
Comfort
7.4
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Overall
7.6
Boarding
7.8
Crew
8.1
Entertainment
6.8
Food
6.9
Comfort
7.4
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Overall
7.6
Boarding
7.8
Crew
8.1
Entertainment
6.8
Food
6.9
Comfort
7.4
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Popular flights
Sao Paulo flight routes
Alternative routes for Chicago to Sao Paulo
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Sao Paulo by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Sao Paulo by cabin class
Find flights from Chicago to Sao Paulo, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Sao Paulo flights
Browse other Chicago and Sao Paulo flight options. Last updated on August 24, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Sao Paulo
Explore flights to Sao Paulo departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 24, 2026.
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 August 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$212 | Average$1,210 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$272 | Average$531 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$407 | Average$680 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$435 | Average$1,032 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$485 | Average$585 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$596 | Average$620 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$615 | Average$831 | FlexibilityNo cancel fee | On-time67% |