Cheapest one-way flights from Chicago to Sao Paulo in May from $267

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

One-Way flights

04 May Arajet
06 May Frontier Airlines
03 May Avianca
09 May Avianca
12 May Avianca
05 May GOL Linhas Aéreas
21 May GOL Linhas Aéreas
17 May GOL Linhas Aéreas
20 May GOL Linhas Aéreas
15 May Copa

Also check the deals for return flights from Chicago to Sao Paulo in May.

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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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