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

Return flights

21 Oct - 11 Nov	Spirit Airlines
24 Oct - 27 Oct	Spirit Airlines
04 Oct - 12 Oct	Frontier Airlines
23 Oct - 11 Nov	Spirit Airlines
12 Oct - 06 Nov	Spirit Airlines
16 Oct - 18 Oct	Avianca
17 Oct - 31 Oct	Avianca
13 Oct - 27 Oct	United
15 Oct - 29 Oct	United
16 Oct - 30 Oct	United
08 Oct - 22 Oct	United
09 Oct - 23 Oct	United
02 Oct - 16 Oct	United
27 Oct - 10 Nov	United
29 Oct - 12 Nov	United
20 Oct - 03 Nov	United
22 Oct - 05 Nov	United
21 Oct - 11 Nov	United	direct
28 Oct - 11 Nov	United	direct
30 Oct - 13 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.

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Cheapest return flights from Chicago to Sao Paulo in October from 457€

Return flights