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

Return flights

26 Oct - 02 Nov	United	direct
29 Oct - 05 Nov	United	direct
01 Oct - 15 Oct	Copa
02 Oct - 13 Oct	Copa
10 Oct - 19 Oct	Copa
08 Oct - 15 Oct	Copa
15 Oct - 22 Oct	Copa
20 Oct - 27 Oct	Copa
21 Oct - 28 Oct	Copa
22 Oct - 29 Oct	Copa
23 Oct - 30 Oct	Copa
27 Oct - 03 Nov	Copa
30 Oct - 06 Nov	Copa
03 Oct - 16 Oct	Copa
25 Oct - 01 Nov	Copa
28 Oct - 04 Nov	Copa
27 Oct - 03 Nov	United	direct
28 Oct - 04 Nov	United	direct
31 Oct - 07 Nov	Copa
25 Oct - 01 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 $475

Return flights