AirHint found the following cheapest one-way flights from New York (LGA) to Chicago (ORD) in May 2026 (see full year).
One-Way flights
| 05 May | Delta | direct | |
| 28 May | Delta | direct | |
| 10 May | Delta | direct | |
| 11 May | United | direct | |
| 15 May | Delta | direct |
Also check the deals for return flights from New York to Chicago in May.
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