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

Return flights

01 May - 10 May	GOL Linhas Aéreas
15 May - 22 May	Spirit Airlines
04 May - 11 May	Frontier Airlines
23 May - 31 May	Arajet
21 May - 31 May	GOL Linhas Aéreas
13 May - 16 May	Avianca
14 May - 21 May	Copa
23 May - 06 Jun	Arajet
29 May - 02 Jun	Avianca
25 May - 01 Jun	GOL Linhas Aéreas
24 May - 01 Jun	GOL Linhas Aéreas
22 May - 01 Jun	GOL Linhas Aéreas
01 May - 10 May	United	direct
24 May - 01 Jun	United	direct
18 May - 04 Jun	United	direct
22 May - 01 Jun	United	direct
25 May - 01 Jun	United	direct
29 May - 02 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 450€

Return flights