AirHint found the following cheapest return flights from Chicago (ORD) to Sao Paulo (GRU) in October 2025 (see full year).

Return flights

15 Oct - 25 Oct	Spirit Airlines
16 Oct - 23 Oct	Spirit Airlines
31 Oct - 10 Nov	Spirit Airlines
10 Oct - 18 Oct	Avianca
10 Oct - 19 Oct	Avianca
30 Oct - 08 Nov	Spirit Airlines
02 Oct - 11 Oct	Avianca
09 Oct - 23 Oct	United	direct
13 Oct - 27 Oct	United	direct
02 Oct - 16 Oct	United	direct
06 Oct - 20 Oct	United	direct
07 Oct - 21 Oct	United	direct
20 Oct - 03 Nov	United	direct
21 Oct - 04 Nov	United	direct
23 Oct - 06 Nov	United	direct
27 Oct - 10 Nov	United	direct
22 Oct - 05 Nov	United
31 Oct - 10 Nov	United	direct
24 Oct - 07 Nov	United	direct
25 Oct - 08 Nov	United	direct

Also check the deals for one-way flights from Chicago to Sao Paulo in October.

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

Cheapest return flights from Chicago to Sao Paulo in October from $624

Return flights