Cheapest one-way flights from Chicago to Sao Paulo in June from $294

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 June 2025 (see full year).

One-Way flights

15 Jun Frontier Airlines
02 Jun Porter Airlines (Canada) Ltd
06 Jun Frontier Airlines
16 Jun Porter Airlines (Canada) Ltd
14 Jun Frontier Airlines
07 Jun Frontier Airlines
24 Jun Porter Airlines (Canada) Ltd
17 Jun Porter Airlines (Canada) Ltd
01 Jun Porter Airlines (Canada) Ltd
27 Jun Porter Airlines (Canada) Ltd

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

Skyscanner

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.

Book a cheap hotel in Sao Paulo

Cheap car rent in Sao Paulo