Cheap Flights from MDW to NYC

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The Cheapest Round-trip Tickets from to New York

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20 April 202622 April 2026DirectFrontier AirlinesRT from 55

The Cheapest Flights for this Month from to New York

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1 April 20262 April 2026DirectSouthwest AirlinesRT from 490
2 April 20269 April 20261 StopFrontier AirlinesRT from 199
3 April 20265 April 20261 StopFrontier AirlinesRT from 286
4 April 20266 April 20261 StopFrontier AirlinesRT from 316
5 April 20269 April 2026DirectSouthwest AirlinesRT from 294
9 April 202611 April 20261 StopFrontier AirlinesRT from 237
10 April 202613 April 20261 StopFrontier AirlinesRT from 246
15 April 202616 April 2026DirectFrontier AirlinesRT from 144
16 April 202619 April 2026DirectFrontier AirlinesRT from 122
17 April 202621 April 2026DirectSouthwest AirlinesRT from 123
18 April 202620 April 20261 StopFrontier AirlinesRT from 163
19 April 202621 April 2026DirectFrontier AirlinesRT from 111
20 April 202622 April 2026DirectFrontier AirlinesRT from 55
23 April 202626 April 20261 StopFrontier AirlinesRT from 113
24 April 202627 April 2026DirectSouthwest AirlinesRT from 164
26 April 202628 April 2026DirectSouthwest AirlinesRT from 121
30 April 20263 May 2026DirectFrontier AirlinesRT from 123
1 May 20263 May 20261 StopFrontier AirlinesRT from 129
12 May 202612 May 2026DirectSouthwest AirlinesRT from 183
22 May 202625 May 2026DirectSouthwest AirlinesRT from 305
1 June 20263 June 2026DirectSouthwest AirlinesRT from 178
20 June 202625 June 2026DirectSouthwest AirlinesRT from 242
21 June 202625 June 2026DirectSouthwest AirlinesRT from 328
26 June 202629 June 2026DirectSouthwest AirlinesRT from 286
30 June 20266 July 2026DirectSouthwest AirlinesRT from 315
1 July 20266 July 2026DirectSouthwest AirlinesRT from 325
2 July 20267 July 2026DirectSouthwest AirlinesRT from 230
10 July 202613 July 2026DirectSouthwest AirlinesRT from 439
16 July 202619 July 2026DirectSouthwest AirlinesRT from 514
23 July 202626 July 20261 StopFrontier AirlinesRT from 338
24 July 202627 July 20261 StopFrontier AirlinesRT from 255
1 August 20269 August 20261 StopFrontier AirlinesRT from 254
3 August 20267 August 2026DirectSouthwest AirlinesRT from 328
13 September 202620 September 2026DirectSouthwest AirlinesRT from 460

The Cheapest Flights from to New York for the Year Ahead

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20 April 202622 April 2026DirectFrontier AirlinesRT from 55
1 May 20263 May 20261 StopFrontier AirlinesRT from 129
1 June 20263 June 2026DirectSouthwest AirlinesRT from 178
2 July 20267 July 2026DirectSouthwest AirlinesRT from 230
1 August 20269 August 20261 StopFrontier AirlinesRT from 254
13 September 202620 September 2026DirectSouthwest AirlinesRT from 460
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