Cheap Flights from NYC to CHI
The Cheapest Round-trip Tickets from New York to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 8 December 2026 | 15 December 2026 | Direct |  | RT from 180 USD |
The Cheapest Flights for this Month from New York to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 16 October 2026 | 19 October 2026 | 1 Stop |  | RT from 322 USD |
| 17 October 2026 | 18 October 2026 | Direct |  | RT from 280 USD |
| 18 October 2026 | 18 October 2026 | Direct | | RT from 361 USD |
| 19 October 2026 | 22 October 2026 | 1 Stop | | RT from 349 USD |
| 20 October 2026 | 22 October 2026 | 1 Stop | | RT from 292 USD |
| 21 October 2026 | 24 October 2026 | 1 Stop | | RT from 282 USD |
| 22 October 2026 | 25 October 2026 | 1 Stop | | RT from 299 USD |
| 28 October 2026 | 1 November 2026 | 1 Stop | | RT from 283 USD |
| 29 October 2026 | 1 November 2026 | Direct |  | RT from 320 USD |
| 30 October 2026 | 2 November 2026 | 1 Stop | | RT from 289 USD |
| 31 October 2026 | 2 November 2026 | 1 Stop | | RT from 286 USD |
| 2 November 2026 | 10 November 2026 | Direct | | RT from 278 USD |
| 3 November 2026 | 10 November 2026 | 1 Stop | | RT from 229 USD |
| 5 November 2026 | 8 November 2026 | Direct |  | RT from 296 USD |
| 6 November 2026 | 8 November 2026 | Direct | | RT from 299 USD |
| 7 November 2026 | 10 November 2026 | 1 Stop | | RT from 258 USD |
| 10 November 2026 | 13 November 2026 | 1 Stop | | RT from 218 USD |
| 12 November 2026 | 15 November 2026 | 1 Stop | | RT from 298 USD |
| 13 November 2026 | 16 November 2026 | 1 Stop | | RT from 196 USD |
| 17 November 2026 | 20 November 2026 | 1 Stop | | RT from 278 USD |
| 20 November 2026 | 26 November 2026 | 1 Stop | | RT from 255 USD |
| 21 November 2026 | 6 December 2026 | 1 Stop | | RT from 293 USD |
| 23 November 2026 | 29 November 2026 | Direct | | RT from 356 USD |
| 24 November 2026 | 30 November 2026 | 1 Stop | | RT from 242 USD |
| 26 November 2026 | 2 December 2026 | Direct | | RT from 207 USD |
| 27 November 2026 | 2 December 2026 | Direct | | RT from 262 USD |
| 28 November 2026 | 28 November 2026 | Direct | | RT from 571 USD |
| 5 December 2026 | 12 December 2026 | 1 Stop | | RT from 266 USD |
| 8 December 2026 | 15 December 2026 | 1 Stop | | RT from 180 USD |
| 10 December 2026 | 14 December 2026 | 1 Stop | | RT from 249 USD |
| 12 December 2026 | 9 January 2027 | 1 Stop | | RT from 257 USD |
| 14 December 2026 | 21 December 2026 | Direct | | RT from 247 USD |
| 19 December 2026 | 4 January 2027 | Direct | | RT from 300 USD |
| 28 December 2026 | 31 December 2026 | Direct | | RT from 300 USD |
| 29 December 2026 | 1 January 2027 | Direct | | RT from 304 USD |
| 1 January 2027 | 11 January 2027 | 1 Stop | | RT from 307 USD |
| 2 January 2027 | 6 January 2027 | Direct | | RT from 358 USD |
| 4 January 2027 | 6 January 2027 | Direct | | RT from 309 USD |
| 11 January 2027 | 17 January 2027 | Direct | | RT from 239 USD |
| 12 January 2027 | 16 January 2027 | 1 Stop | | RT from 289 USD |
| 28 January 2027 | 1 February 2027 | 1 Stop | | RT from 270 USD |
| 20 April 2027 | 26 April 2027 | Direct | | RT from 323 USD |
| 6 June 2027 | 9 June 2027 | Direct | | RT from 327 USD |
| 9 August 2027 | 23 August 2027 | Direct | | RT from 303 USD |
| 13 August 2027 | 17 August 2027 | Direct | | RT from 303 USD |
The Cheapest Flights from New York to Chicago for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 17 October 2026 | 18 October 2026 | Direct | | RT from 280 USD |
| 13 November 2026 | 16 November 2026 | 1 Stop | | RT from 196 USD |
| 8 December 2026 | 15 December 2026 | 1 Stop | | RT from 180 USD |
| 11 January 2027 | 17 January 2027 | Direct | | RT from 239 USD |
| 20 April 2027 | 26 April 2027 | Direct | | RT from 323 USD |
| 6 June 2027 | 9 June 2027 | Direct | | RT from 327 USD |
| 9 August 2027 | 23 August 2027 | Direct | | RT from 303 USD |