Cheapest return flights from Chicago to Sao Paulo in May from $622

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

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

Return flights

31 May - 06 Jun Frontier Airlines
31 May - 07 Jun Frontier Airlines
31 May - 08 Jun Frontier Airlines
30 May - 07 Jun Frontier Airlines
30 May - 08 Jun Frontier Airlines
16 May - 31 May Frontier Airlines
16 May - 29 May Frontier Airlines
22 May - 08 Jun Porter Airlines (Canada) Ltd
23 May - 27 May Porter Airlines (Canada) Ltd
08 May - 11 May LATAM Airlines Group
09 May - 17 May Porter Airlines (Canada) Ltd
19 May - 31 May LATAM Airlines Group
29 May - 08 Jun Delta
21 May - 04 Jun Delta
18 May - 15 Jun Delta
25 May - 04 Jun LATAM Airlines Group
21 May - 31 May LATAM Airlines Group
19 May - 29 May LATAM Airlines Group
17 May - 27 May LATAM Airlines Group
01 May - 11 May LATAM Airlines Group

Also check the deals for one-way 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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