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

Return flights

07 Sep - 14 Sep	jetBlue
05 Sep - 15 Sep	GOL Linhas Aéreas
07 Sep - 17 Sep	GOL Linhas Aéreas
11 Sep - 21 Sep	jetBlue
17 Sep - 27 Sep	GOL Linhas Aéreas
11 Sep - 18 Sep	Avianca
17 Sep - 24 Sep	GOL Linhas Aéreas
04 Sep - 11 Sep	United	direct
07 Sep - 14 Sep	United	direct
10 Sep - 17 Sep	United	direct
25 Sep - 05 Oct	United	direct
25 Sep - 02 Oct	United	direct
25 Sep - 04 Oct	Copa
24 Sep - 01 Oct	Copa
29 Sep - 06 Oct	Copa
30 Sep - 07 Oct	Copa
25 Sep - 26 Oct	Copa
26 Sep - 03 Oct	Copa
26 Sep - 26 Oct	Copa
10 Sep - 07 Oct	Copa

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 $470

Return flights