Cheapest one-way flights from Chicago to Sao Paulo in May from 271€

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

One-Way flights

19 May Frontier Airlines
04 May Frontier Airlines
20 May Frontier Airlines
15 May Frontier Airlines
27 May Frontier Airlines
25 May Frontier Airlines
21 May Porter Airlines (Canada) Ltd
26 May LATAM Airlines Group

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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