Cheap Flights from NYC to CHI
The Cheapest Round-trip Tickets from New York to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 21 May 2025 | 29 May 2025 | Direct |  | RT from 94 |
The Cheapest Flights for this Month from New York to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 4 May 2025 | 8 May 2025 | 1 Stop |  | RT from 275 |
| 5 May 2025 | 5 May 2025 | 1 Stop | | RT from 262 |
| 6 May 2025 | 13 May 2025 | Direct | | RT from 98 |
| 8 May 2025 | 8 May 2025 | Direct |  | RT from 202 |
| 10 May 2025 | 17 May 2025 | 1 Stop | | RT from 174 |
| 11 May 2025 | 14 May 2025 | Direct | | RT from 123 |
| 12 May 2025 | 14 May 2025 | Direct | | RT from 112 |
| 13 May 2025 | 14 May 2025 | Direct | | RT from 121 |
| 15 May 2025 | 16 May 2025 | Direct |  | RT from 185 |
| 19 May 2025 | 21 May 2025 | Direct | | RT from 112 |
| 21 May 2025 | 29 May 2025 | Direct | | RT from 94 |
| 23 May 2025 | 25 May 2025 | 1 Stop | | RT from 162 |
| 24 May 2025 | 28 May 2025 | Direct | | RT from 95 |
| 25 May 2025 | 27 May 2025 | Direct | | RT from 95 |
| 2 June 2025 | 9 June 2025 | Direct | | RT from 105 |
| 11 June 2025 | 20 June 2025 | Direct | | RT from 110 |
| 12 June 2025 | 14 June 2025 | Direct | | RT from 106 |
| 17 June 2025 | 20 June 2025 | Direct | | RT from 105 |
| 23 June 2025 | 26 June 2025 | Direct | | RT from 159 |
| 25 July 2025 | 31 July 2025 | Direct | | RT from 197 |
| 25 December 2025 | 29 December 2025 | 1 Stop | | RT from 287 |
| 26 December 2025 | 28 December 2025 | Direct |  | RT from 346 |
The Cheapest Flights from New York to Chicago for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 21 May 2025 | 29 May 2025 | Direct | | RT from 94 |
| 2 June 2025 | 9 June 2025 | Direct | | RT from 105 |
| 25 July 2025 | 31 July 2025 | Direct | | RT from 197 |
| 25 December 2025 | 29 December 2025 | 1 Stop | | RT from 287 |