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

Return flights

19 Jan - 01 Feb	Arajet
21 Jan - 04 Feb	Arajet
21 Jan - 28 Jan	Arajet
19 Jan - 22 Feb	Copa
29 Jan - 02 Feb	Copa
18 Jan - 02 Feb	Copa
31 Jan - 08 Feb	Arajet
19 Jan - 01 Feb	United	direct
24 Jan - 07 Feb	United	direct
18 Jan - 02 Feb	United	direct
14 Jan - 18 Jan	Spirit Airlines
09 Jan - 19 Jan	Copa
06 Jan - 16 Jan	Frontier Airlines
11 Jan - 18 Jan	Spirit Airlines
11 Jan - 18 Jan	United	direct
05 Jan - 18 Jan	United	direct
02 Jan - 17 Jan	United	direct
29 Jan - 02 Feb	United	direct
14 Jan - 18 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 429€

Return flights