AirHint found the following cheapest return flights from Chicago (ORD) to Sao Paulo (GRU) in January 2026 (see full year).

Return flights

24 Jan - 07 Feb	GOL Linhas Aéreas
26 Jan - 09 Feb	GOL Linhas Aéreas
17 Jan - 24 Jan	GOL Linhas Aéreas
13 Jan - 20 Jan	GOL Linhas Aéreas
19 Jan - 22 Feb	GOL Linhas Aéreas
15 Jan - 26 Jan	GOL Linhas Aéreas
31 Jan - 08 Feb	GOL Linhas Aéreas
30 Jan - 08 Feb	Copa
08 Jan - 31 Jan	Copa
02 Jan - 11 Jan	Spirit Airlines
02 Jan - 10 Jan	Spirit Airlines
24 Jan - 07 Feb	United	direct
21 Jan - 04 Feb	United	direct
26 Jan - 09 Feb	United	direct
22 Jan - 21 Feb	United
02 Jan - 11 Jan	United	direct
02 Jan - 04 Jan	GOL Linhas Aéreas
02 Jan - 10 Jan	United	direct

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

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 January from $546

Return flights