Cheapest one-way flights from Chicago to Sao Paulo in May from $218

AirHint found the following cheapest one-way flights from Chicago (ORD) to Sao Paulo (GRU) in May 2026 (see full year).

One-Way flights

05 May Spirit Airlines
02 May Arajet
16 May Frontier Airlines
04 May Frontier Airlines
15 May Frontier Airlines
19 May Frontier Airlines
17 May Frontier Airlines
01 May GOL Linhas Aรฉreas
20 May GOL Linhas Aรฉreas
28 May Copa

Also check the deals for return flights from Chicago to Sao Paulo in May.

Powered by

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

Book a cheap hotel in Sao Paulo

Cheap car rent in Sao Paulo

Feel free to contact us with any feedback or request another flight research.