Cheapest one-way flights from Chicago to Sao Paulo in May from $369

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

One-Way flights

11 May Porter Airlines (Canada) Ltd
05 May Porter Airlines (Canada) Ltd
10 May Porter Airlines (Canada) Ltd
28 May Porter Airlines (Canada) Ltd
18 May Porter Airlines (Canada) Ltd
13 May Porter Airlines (Canada) Ltd
08 May Porter Airlines (Canada) Ltd
02 May Delta

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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