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

Best time to book flights for Chicago (MDW) to Sao Paulo (GRU) flights at AirHint

AirHint found the following cheapest one-way flights from Chicago (MDW) to Sao Paulo (GRU) in May 2025 (see full year).

One-Way flights

23 May Porter Airlines (Canada) Ltd
19 May Frontier Airlines
11 May Frontier Airlines
24 May Porter Airlines (Canada) Ltd
27 May Porter Airlines (Canada) Ltd
29 May Porter Airlines (Canada) Ltd
06 May Frontier Airlines
13 May Porter Airlines (Canada) Ltd
14 May Porter Airlines (Canada) Ltd
20 May Porter Airlines (Canada) Ltd

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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