
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $556 (Kiwi.com) |
One-way from | $232 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $685 |
Good round-trip deal | $825 or less |
Good one-way deal | $345 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSao Paulo
ORD - GRU
ORDGRU
Chicago O'Hare Intl
Mon 6/1
3:21 pm-6:30 am
1 stop13h 09m
Sao Paulo Guarulhos Intl
Fri 7/31
11:10 am-4:00 am
1 stop18h 50m
ChicagoSao Paulo
ORD - GRU
ORDGRU
Chicago O'Hare Intl
Mon 6/22
8:02 am-12:10 am
1 stop14h 08m
Sao Paulo Guarulhos Intl
Wed 7/8
11:10 am-4:00 am
1 stop18h 50m
ChicagoSao Paulo
ORD - GRU
ORDGRU
Chicago O'Hare Intl
Sat 6/20
8:02 am-3:50 am
1 stop17h 48m
Sao Paulo Guarulhos Intl
Mon 7/20
3:15 am-12:01 am
1 stop22h 46m
ChicagoSao Paulo
ORD - GRU
ORDGRU
Chicago O'Hare Intl
Sun 6/28
3:21 pm-6:30 am
1 stop13h 09m
Sao Paulo Guarulhos Intl
Sun 7/5
11:10 am-4:00 am
1 stop18h 50m
ChicagoSao Paulo
MDW - GRU
MDWGRU
Chicago Midway
Mon 5/11
12:51 pm-5:40 am
1 stop14h 49m
Sao Paulo Guarulhos Intl
Fri 5/22
10:50 pm-3:26 pm
1 stop18h 36m
ChicagoSao Paulo
ORD - VCP
ORDVCP
Chicago O'Hare Intl
Wed 4/15
5:34 pm-5:45 pm
1 stop22h 11m
Sao Paulo Viracopos
Sat 4/18
8:30 am-2:20 pm
3 stops31h 50m
ChicagoSao Paulo
ORD - GRU
ORDGRU
Chicago O'Hare Intl
Tue 3/10
5:15 am-4:15 pm
3 stops33h 00m
Sao Paulo Guarulhos Intl
Wed 3/18
5:25 pm-8:25 am
2 stops17h 00m
ChicagoSao Paulo
ORD - VCP
ORDVCP
Chicago O'Hare Intl
Tue 5/19
3:31 pm-11:00 am
2 stops17h 29m
Sao Paulo Viracopos
Wed 6/3
10:10 am-11:10 pm
1 stop15h 00m
ChicagoSao Paulo
ORD - CGH
ORDCGH
Chicago O'Hare Intl
Fri 4/17
2:17 pm-10:25 pm
2 stops30h 08m
Sao Paulo Congonhas
Mon 5/11
6:30 am-10:57 pm
2 stops18h 27m
ChicagoSao Paulo
ORD - CGH
ORDCGH
Chicago O'Hare Intl
Fri 8/21
2:32 pm-8:00 am
2 stops39h 28m
Sao Paulo Congonhas
Tue 8/25
6:30 am-10:31 pm
2 stops18h 01m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
To ensure you get the cheapest price possible for a flight from Chicago to Sao Paulo, you should look to book at least 3 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.
Currently, May is the cheapest month in which you can book a flight from Chicago to Sao Paulo (average of $376). Flying from Chicago to Sao Paulo in August is currently the most expensive (average of $696). 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.
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.
The most flights from CHI to SAO are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
Panama City (PTY) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to Sao Paulo on Cheapflights.
Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of $672.
Flights via Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 12h 55m.
Flights via Panama City (PTY) offer the fastest connection on this route, with an average layover time of 1h 18m.
About 41% of weekly flights between Chicago and Sao Paulo have experienced delays in the past year, with the average delay time being 182 minutes.
Historically, flights departing in the evening are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
Thursday 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.
Over the last year, United Airlines have had the lowest number of delays on this route, with just 41% of flights being delayed.
Entertainment
Food
Crew
Overall
Boarding
Comfort
Reviews
Juan,Dec 2025
EZE - PTY
Entertainment
Food
Crew
Overall
Boarding
Comfort
Reviews
Juan,Dec 2025
EZE - PTY
Entertainment
Food
Crew
Overall
Boarding
Comfort
Reviews
Juan,Dec 2025
EZE - PTY
Entertainment
Food
Crew
Overall
Boarding
Comfort
Reviews
Juan,Dec 2025
EZE - PTY
Entertainment
Food
Crew
Overall
Boarding
Comfort
Reviews
Juan,Dec 2025
EZE - PTY
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$359 | Average$673 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$435 | Average$981 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$471 | Average$736 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$500 | Average$1,317 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$531 | Average$607 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$596 | Average$610 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$615 | Average$794 | FlexibilityNo cancel fee | On-time67% |