Today's drop ·
Cheap flights from Chicago to São Paulo
$604 round trip right now, 30% under the $857 this route usually costs.
How cheap is this?
Telly prices every departure date six months out on this route, for trips of 2 to 14 nights, and measures each fare against what the route usually costs. The cheapest round trip right now is $604 on Arajet, 1 stop, against a usual $857. Best price on this route in a month.
When to go
The cheapest dates fall in Feb–Apr, for trips of 2 to 10 nights. Feb in São Paulo runs around 74°. The dates come picked because a cheap fare only exists on certain days; the exact ones and the booking link are in the app.
Passport required
São Paulo is outside the US and Canada, so you need a passport. Every flight on Telly leaves the country; that is the whole filter.
Questions about this route
How much is a flight from Chicago to São Paulo?+
Right now $604 round trip, on Arajet. The route usually costs $857, so this fare is 30% under. Checked Nov 4, 2026.
When are the cheapest dates to fly to São Paulo?+
The cheapest dates Telly found are in Feb–Apr, for trips of 2 to 10 nights. It prices every departure date six months out on this route and keeps only the lowest. The exact dates are in the app.
Do I need a passport to fly from Chicago to São Paulo?+
Yes. São Paulo is outside the US and Canada, and every flight on Telly leaves the country, so every one needs a passport.
