Cheap Flights from NYC to MDW
The Cheapest Round-trip Tickets from New York to
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 23 September 2026 | 30 September 2026 | Direct |  | RT from 241 USD |
The Cheapest Flights for this Month from New York to
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 14 September 2026 | 16 September 2026 | Direct |  | RT from 394 USD |
| 15 September 2026 | 17 September 2026 | 1 Stop | | RT from 336 USD |
| 16 September 2026 | 18 September 2026 | 1 Stop | | RT from 306 USD |
| 17 September 2026 | 20 September 2026 | Direct | | RT from 297 USD |
| 18 September 2026 | 21 September 2026 | 1 Stop | | RT from 364 USD |
| 21 September 2026 | 23 September 2026 | Direct | | RT from 317 USD |
| 23 September 2026 | 30 September 2026 | 1 Stop | | RT from 241 USD |
| 25 September 2026 | 28 September 2026 | 1 Stop | | RT from 278 USD |
| 26 September 2026 | 29 September 2026 | Direct | | RT from 313 USD |
| 30 September 2026 | 11 October 2026 | Direct | | RT from 295 USD |
| 1 October 2026 | 4 October 2026 | Direct | | RT from 300 USD |
| 3 October 2026 | 5 October 2026 | 1 Stop | | RT from 264 USD |
| 7 October 2026 | 19 October 2026 | Direct | | RT from 280 USD |
| 8 October 2026 | 25 October 2026 | 1 Stop | | RT from 343 USD |
| 12 October 2026 | 26 October 2026 | 1 Stop | | RT from 355 USD |
| 15 October 2026 | 18 October 2026 | Direct | | RT from 285 USD |
| 16 October 2026 | 18 October 2026 | Direct | | RT from 259 USD |
| 18 October 2026 | 22 October 2026 | Direct | | RT from 368 USD |
| 26 October 2026 | 1 November 2026 | Direct | | RT from 338 USD |
| 29 October 2026 | 1 November 2026 | Direct | | RT from 274 USD |
| 1 November 2026 | 6 November 2026 | Direct | | RT from 274 USD |
| 6 November 2026 | 7 November 2026 | Direct | | RT from 297 USD |
| 7 November 2026 | 8 November 2026 | Direct | | RT from 297 USD |
| 9 November 2026 | 10 November 2026 | 1 Stop | | RT from 287 USD |
| 13 November 2026 | 15 November 2026 | Direct | | RT from 284 USD |
| 23 November 2026 | 1 December 2026 | 1 Stop | | RT from 260 USD |
| 25 November 2026 | 27 November 2026 | Direct | | RT from 277 USD |
| 5 December 2026 | 10 December 2026 | Direct | | RT from 277 USD |
| 23 December 2026 | 3 January 2027 | Direct | | RT from 623 USD |
| 1 February 2027 | 7 February 2027 | Direct | | RT from 301 USD |
| 4 February 2027 | 7 February 2027 | Direct | | RT from 281 USD |
| 8 February 2027 | 15 February 2027 | Direct | | RT from 315 USD |
| 21 April 2027 | 25 April 2027 | Direct | | RT from 331 USD |
The Cheapest Flights from New York to for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 23 September 2026 | 30 September 2026 | 1 Stop | | RT from 241 USD |
| 16 October 2026 | 18 October 2026 | Direct | | RT from 259 USD |
| 23 November 2026 | 1 December 2026 | 1 Stop | | RT from 260 USD |
| 5 December 2026 | 10 December 2026 | Direct | | RT from 277 USD |
| 4 February 2027 | 7 February 2027 | Direct | | RT from 281 USD |
| 21 April 2027 | 25 April 2027 | Direct | | RT from 331 USD |