
Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $538 (Kiwi.com) |
One-way from | $202 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $1,121 |
Good round-trip deal | $837 or less |
Good one-way deal | $2,413 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSao Paulo
ORD - CGH
ORDCGH
Chicago O'Hare Intl
Thu 3/5
7:10 am-4:30 pm
2 stops30h 20m
Sao Paulo Congonhas
Sun 3/8
2:40 pm-10:04 pm
2 stops33h 24m
ChicagoSao Paulo
ORD - GRU
ORDGRU
Chicago O'Hare Intl
Fri 5/15
7:20 pm-2:42 am
3 stops29h 22m
Sao Paulo Guarulhos Intl
Fri 5/22
1:45 am-1:15 pm
1 stop13h 30m
ChicagoSao Paulo
ORD - GRU
ORDGRU
Chicago O'Hare Intl
Sun 1/18
10:20 pm-10:40 pm
1 stop21h 20m
Sao Paulo Guarulhos Intl
Thu 1/22
2:40 am-8:20 pm
1 stop20h 40m
ChicagoSao Paulo
ORD - VCP
ORDVCP
Chicago O'Hare Intl
Thu 3/5
2:12 pm-9:00 am
2 stops39h 48m
Sao Paulo Viracopos
Sun 3/8
10:10 am-11:38 pm
1 stop15h 28m
ChicagoSao Paulo
ORD - GRU
ORDGRU
Chicago O'Hare Intl
Fri 5/8
2:50 pm-1:00 pm
2 stops20h 10m
Sao Paulo Guarulhos Intl
Sun 5/24
7:20 am-1:15 pm
1 stop31h 55m
ChicagoSao Paulo
ORD - GRU
ORDGRU
Chicago O'Hare Intl
Sat 5/16
2:35 pm-2:10 am
1 stop33h 35m
Sao Paulo Guarulhos Intl
Sat 5/30
4:45 pm-9:25 pm
2 stops30h 40m
ChicagoSao Paulo
ORD - GRU
ORDGRU
Chicago O'Hare Intl
Thu 2/19
2:22 pm-6:30 am
1 stop13h 08m
Sao Paulo Guarulhos Intl
Tue 3/3
5:25 pm-9:39 am
2 stops19h 14m
ChicagoSao Paulo
ORD - VCP
ORDVCP
Chicago O'Hare Intl
Mon 2/9
2:22 pm-7:40 pm
2 stops26h 18m
Sao Paulo Viracopos
Mon 2/16
11:20 pm-11:22 am
1 stop15h 02m
ChicagoSao Paulo
ORD - GRU
ORDGRU
Chicago O'Hare Intl
Sun 2/15
10:20 pm-1:35 am
1 stop24h 15m
Sao Paulo Guarulhos Intl
Thu 2/19
9:40 pm-9:24 pm
2 stops50h 44m
ChicagoSao Paulo
ORD - GRU
ORDGRU
Chicago O'Hare Intl
Fri 5/8
3:21 pm-6:30 am
1 stop13h 09m
Sao Paulo Guarulhos Intl
Sun 5/24
5:25 am-1:15 am
1 stop21h 50m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 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 49 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 $694). 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.
Unlike at noon, when flights are generally more expensive, you can save up to 27% on flights from Chicago to Sao Paulo by exploring options for tickets in the morning.
Travelers seeking maximum savings on their Chicago to Sao Paulo flight should consider departing on Monday mornings when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 89% 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 40% of weekly flights between Chicago and Sao Paulo have experienced delays in the past year, with the average delay time being 169 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, Atlas Air have had the lowest number of delays on this route, with just 38% of flights being delayed.
Overall
Crew
Entertainment
Food
Boarding
Comfort
Reviews
Juan,Dec 2025
EZE - PTY
Overall
Crew
Entertainment
Food
Boarding
Comfort
Reviews
Juan,Dec 2025
EZE - PTY
Overall
Crew
Entertainment
Food
Boarding
Comfort
Reviews
Juan,Dec 2025
EZE - PTY
Overall
Crew
Entertainment
Food
Boarding
Comfort
Reviews
Juan,Dec 2025
EZE - PTY
Overall
Crew
Entertainment
Food
Boarding
Comfort
Reviews
Juan,Dec 2025
EZE - PTY
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$376 | Average$676 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$435 | Average$983 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$500 | Average$1,058 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$531 | Average$637 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$572 | Average$803 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$596 | Average$610 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$615 | Average$823 | FlexibilityNo cancel fee | On-time67% |