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

Return flights

11 May - 18 May	Copa
06 May - 20 May	Copa
14 May - 22 May	Copa
05 May - 12 May	Copa
04 May - 11 May	Copa
01 May - 08 May	Copa
01 May - 11 May	Copa
15 May - 22 May	Copa
03 May - 10 May	Copa
10 May - 17 May	Copa
25 May - 21 Jun	Arajet
18 May - 04 Jun	Arajet
25 May - 24 Jun	Arajet
25 May - 16 Jun	Arajet
28 May - 06 Jun	Avianca
29 May - 02 Jun	Avianca
19 May - 16 Jun	Spirit Airlines
20 May - 16 Jun	GOL Linhas Aéreas
18 May - 04 Jun	United	direct
28 May - 06 Jun	United	direct

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

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 May from $440

Return flights