AirHint found the following cheapest return flights from Chicago (MDW) to Sao Paulo (GRU) in January 2026 (see full year).

Return flights

01 Jan - 17 Jan	Frontier Airlines
03 Jan - 17 Jan	Frontier Airlines
02 Jan - 17 Jan	LATAM Airlines Group
09 Jan - 17 Jan	Delta
24 Jan - 06 Feb	Delta
31 Jan - 08 Feb	Delta
10 Jan - 17 Jan	Delta
05 Jan - 20 Jan	LATAM Airlines Group
05 Jan - 30 Jan	Delta
02 Jan - 10 Jan	Delta
05 Jan - 11 Jan	Delta
05 Jan - 10 Jan	Delta

Also check the deals for one-way flights from Chicago to Sao Paulo in January.

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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Cheapest return flights from Chicago to Sao Paulo in January from 897€

Return flights