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

Return flights

04 Sep - 08 Sep	Spirit Airlines
19 Sep - 03 Oct	Spirit Airlines
06 Sep - 17 Sep	Spirit Airlines
09 Sep - 23 Sep	United	direct
10 Sep - 24 Sep	United	direct
17 Sep - 01 Oct	United	direct
22 Sep - 06 Oct	United	direct
02 Sep - 16 Sep	United
11 Sep - 25 Sep	United
15 Sep - 29 Sep	United
16 Sep - 30 Sep	United
29 Sep - 13 Oct	United
30 Sep - 14 Oct	United
06 Sep - 17 Sep	United	direct
24 Sep - 08 Oct	United
28 Sep - 12 Oct	United	direct
05 Sep - 19 Sep	United
27 Sep - 11 Oct	United

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 $568

Return flights