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

Return flights

06 Sep - 14 Sep	United	direct
11 Sep - 18 Sep	United	direct
14 Sep - 24 Sep	United	direct
07 Sep - 14 Sep	United	direct
08 Sep - 29 Sep	United	direct
17 Sep - 24 Sep	United	direct
22 Sep - 29 Sep	United	direct
23 Sep - 30 Sep	United	direct
14 Sep - 21 Sep	United	direct
10 Sep - 17 Sep	United	direct
25 Sep - 05 Oct	United	direct
29 Sep - 06 Oct	Copa
25 Sep - 02 Oct	United	direct
25 Sep - 04 Oct	Copa
24 Sep - 01 Oct	Copa
30 Sep - 07 Oct	Copa
26 Sep - 03 Oct	Copa
24 Sep - 01 Oct	United	direct
28 Sep - 05 Oct	United	direct
29 Sep - 06 Oct	United	direct

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

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 September from 405€

Return flights