Cheap Flights from MDW to NYC

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The Cheapest Round-trip Tickets from to New York

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26 October 202627 October 2026DirectSouthwest AirlinesRT from 147

The Cheapest Flights for this Month from to New York

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16 July 202623 July 20261 StopSouthwest AirlinesRT from 413
17 July 202619 July 2026DirectSouthwest AirlinesRT from 474
18 July 202619 July 20261 StopSouthwest AirlinesRT from 384
19 July 202623 July 20261 StopFrontier AirlinesRT from 396
26 July 202631 July 20261 StopSouthwest AirlinesRT from 420
28 July 20261 August 2026DirectSouthwest AirlinesRT from 228
29 July 202629 July 2026DirectSouthwest AirlinesRT from 406
30 July 20261 August 2026DirectSouthwest AirlinesRT from 226
31 July 20262 August 20261 StopSouthwest AirlinesRT from 240
1 August 20265 August 20261 StopSouthwest AirlinesRT from 241
4 August 20268 August 20261 StopFrontier AirlinesRT from 263
6 August 20269 August 2026DirectSouthwest AirlinesRT from 244
11 August 202614 August 2026DirectSouthwest AirlinesRT from 251
12 August 202618 August 2026DirectSouthwest AirlinesRT from 189
21 August 202624 August 2026DirectSouthwest AirlinesRT from 213
24 August 202631 August 2026DirectSouthwest AirlinesRT from 179
26 August 20262 September 2026DirectSouthwest AirlinesRT from 215
27 August 202627 August 2026DirectSouthwest AirlinesRT from 221
28 August 202628 August 2026DirectSouthwest AirlinesRT from 308
31 August 20265 September 2026DirectSouthwest AirlinesRT from 217
1 September 20268 September 2026DirectSouthwest AirlinesRT from 216
3 September 20266 September 20261 StopFrontier AirlinesRT from 249
4 September 20267 September 20261 StopFrontier AirlinesRT from 267
10 September 202613 September 20261 StopFrontier AirlinesRT from 250
8 October 202611 October 2026DirectSouthwest AirlinesRT from 286
10 October 202612 October 20261 StopFrontier AirlinesRT from 147
22 October 202625 October 20261 StopSouthwest AirlinesRT from 232
25 October 20264 November 2026DirectSouthwest AirlinesRT from 190
26 October 202627 October 20261 StopSouthwest AirlinesRT from 147
27 October 20264 November 2026DirectSouthwest AirlinesRT from 216
28 October 202630 October 2026DirectSouthwest AirlinesRT from 196
2 November 20264 November 2026DirectSouthwest AirlinesRT from 198
7 December 202610 December 2026DirectSouthwest AirlinesRT from 219
30 December 20262 January 2027DirectSouthwest AirlinesRT from 460

The Cheapest Flights from to New York for the Year Ahead

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30 July 20261 August 2026DirectSouthwest AirlinesRT from 226
24 August 202631 August 2026DirectSouthwest AirlinesRT from 179
1 September 20268 September 2026DirectSouthwest AirlinesRT from 216
26 October 202627 October 20261 StopSouthwest AirlinesRT from 147
2 November 20264 November 2026DirectSouthwest AirlinesRT from 198
7 December 202610 December 2026DirectSouthwest AirlinesRT from 219
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