Cheapest return flights from Chicago to Sao Paulo in May from $508

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

Return flights

16 May - 24 May Arajet
18 May - 21 May Spirit Airlines
11 May - 18 May Arajet
10 May - 17 May Copa
19 May - 25 May Copa
06 May - 18 May Copa
07 May - 18 May Copa
06 May - 20 May Avianca
15 May - 24 May Spirit Airlines
15 May - 29 May Spirit Airlines
29 May - 02 Jun Avianca
29 May - 02 Jun United direct

Also check the deals for one-way 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.