AirHint found the following cheapest one-way flights from Chicago (ORD) to Sao Paulo (GRU) in May 2026 (see full year).
One-Way flights
| 11 May | Arajet | ||
| 25 May | Arajet | ||
| 27 May | Arajet | ||
| 18 May | Arajet | ||
| 13 May | Arajet | ||
| 28 May | Avianca | ||
| 11 May | United | direct | |
| 13 May | United | direct | |
| 28 May | United | direct | |
| 25 May | United | direct |
Also check the deals for return flights from Chicago to Sao Paulo in May.
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