RareNonstop · 5h
CHI to SJUPuerto Rico
San Juan
$162
usually $340
−52%
Most monthly lows $287–$340. Cheaper than every other month on record (3).
Flights · CHI → SAO
Chicago to São Paulo
Best fare, round trip
$938
Too little price history on this route to compare — the fare is shown as found.
Found
- Depart
- Mon 9 Nov
- Return
- Sat 14 Nov
- Stay
- 5 nights
- Flight
- 1 stop · 12h
- Airline
Arajet
Cached fare — the booking search re-prices live before you pay.
BrazilSão PauloNot pretty and not trying to be — the food, the music and the fares out of here beat Rio on every count.Best windowMar–May · Sep–NovAirportsGuarulhos (GRU) · Congonhas (CGH) · Viracopos (VCP)Every route into São PauloFare seasonality
When this route gets cheap.
The cheapest itinerary we are tracking makes one stop and takes about 12 hours outbound, on a 5-night trip — ticketed under Arajet, which on a connecting fare need not operate every leg. At $938 for 8,408 km each way, that works out to about $56 per 1,000 km flown. That is above the $44 per 1,000 km typical of long-haul fares here. Across the 27 departure cities we track at a similar distance from São Paulo, this fare ranks 24th — 1.7× the $542 we hold from Mexico City. For context, the middle fare among the 38 routes of similar length we watch out of Chicago is $734. We have 2 months of cached prices for this route so far — not enough to call a fare cheap or expensive, so we publish the price without a percentage. Fare history here is still too short to name a cheap season. The best time to be in São Paulo: Mar–May · Sep–Nov.
The 3 days we hold a cached fare for
Press a date to compare its fares
The median cached fare across this calendar is 117% higher than when tracking began on 19 Aug — $585 then versus $1,271 now, across 6 recorded snapshots. This is a calendar-level trend, so an individual deal above can be lower. The lowest single day we have seen here is $529, on 31 Oct.
These are the only days we have a cached price for on this route so far — not the only days it flies. The search above covers any date.
Cached fares · checked 15 Oct 2026
We are still collecting this route's months — 2 months of cached prices so far, too few to chart.
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ Guarulhos (GRU) · Congonhas (CGH) · Viracopos (VCP)
- Flight time
- ≈12 hours outbound
- Distance
- ≈8,408 km each way
- Airlines on the board
- Arajet
- Itineraries
- Connections on current fares
- Best months to visit
- Mar–May · Sep–Nov
Good to know
CHI → SAO, answered.
How far in advance should I book CHI → São Paulo?
We do not publish a number for this, because we cannot measure it yet. Answering it honestly means watching the same departure date on this route over many weeks as it approaches, and that archive is still filling up — so any "book N days ahead" figure here would be borrowed from somewhere else rather than measured. Our guide Why flight prices change covers the levers we can measure.
Are there nonstop flights from Chicago to São Paulo?
The current cheapest fares involve a connection, ticketed under Arajet. We hold no nonstop fare on this route right now, which does not mean none flies — search your exact dates to see what does.
Are these prices guaranteed?
No — these are cached fares found on real searches (this one on 17 October). Airlines reprice constantly, so the booking search re-checks the live price before you pay. Fresher finds are far more likely to still be available.
Next step
Sleeping in São Paulo?
Lock the flight first — then compare stays for 9–14 Nov · 5 nights.
Browse hotelsMissed it?
Cached fares expire. This route has a feed of its own — follow it and the next CHI → SAO drop reaches you as soon as we find it.
Follow this route’s feedKeep browsing
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