Cheapest one-way flights from Chicago to Sao Paulo in October from $295

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

One-Way flights

12 Oct Arajet
14 Oct GOL Linhas Aéreas
11 Oct Air Canada
11 Oct United direct
14 Oct United direct

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

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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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