Cheap Flights from MDW to NYC

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The Cheapest Round-trip Tickets from to New York

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30 April 20265 May 2026DirectFrontier AirlinesRT from 99

The Cheapest Flights for this Month from to New York

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16 April 202619 April 20261 StopFrontier AirlinesRT from 201
17 April 202618 April 2026DirectFrontier AirlinesRT from 207
18 April 202620 April 20261 StopFrontier AirlinesRT from 232
21 April 202621 April 20261 StopFrontier AirlinesRT from 246
23 April 202626 April 2026DirectFrontier AirlinesRT from 175
25 April 20262 May 20261 StopFrontier AirlinesRT from 108
27 April 20264 May 20261 StopFrontier AirlinesRT from 168
29 April 20262 May 20261 StopFrontier AirlinesRT from 111
30 April 20265 May 20261 StopFrontier AirlinesRT from 99
1 May 20263 May 2026DirectFrontier AirlinesRT from 184
3 May 20265 May 20261 StopFrontier AirlinesRT from 143
5 May 20268 May 2026DirectSouthwest AirlinesRT from 207
7 May 20269 May 2026DirectSouthwest AirlinesRT from 178
13 May 202613 May 2026DirectSouthwest AirlinesRT from 209
15 May 202620 May 2026DirectSouthwest AirlinesRT from 177
17 May 202619 May 2026DirectSouthwest AirlinesRT from 231
18 May 202620 May 2026DirectSouthwest AirlinesRT from 268
20 May 20263 June 20261 StopFrontier AirlinesRT from 170
1 June 20263 June 20261 StopFrontier AirlinesRT from 200
2 June 20264 June 2026DirectSouthwest AirlinesRT from 212
3 June 20265 June 2026DirectSouthwest AirlinesRT from 236
12 June 202615 June 2026DirectSouthwest AirlinesRT from 205
6 July 202620 July 20261 StopSouthwest AirlinesRT from 264
27 July 202629 July 2026DirectSouthwest AirlinesRT from 214
8 August 202611 August 20261 StopFrontier AirlinesRT from 240

The Cheapest Flights from to New York for the Year Ahead

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30 April 20265 May 20261 StopFrontier AirlinesRT from 99
3 May 20265 May 20261 StopFrontier AirlinesRT from 143
1 June 20263 June 20261 StopFrontier AirlinesRT from 200
27 July 202629 July 2026DirectSouthwest AirlinesRT from 214
8 August 202611 August 20261 StopFrontier AirlinesRT from 240
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