Cheap Flights from MDW to NYC

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The Cheapest Round-trip Tickets from to New York

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5 June 20267 June 2026DirectFrontier AirlinesRT from 121

The Cheapest Flights for this Month from to New York

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30 April 20263 May 2026DirectFrontier AirlinesRT from 200
1 May 20261 May 20261 StopFrontier AirlinesRT from 335
2 May 20264 May 2026DirectFrontier AirlinesRT from 278
3 May 20265 May 20261 StopFrontier AirlinesRT from 339
4 May 20267 May 20261 StopFrontier AirlinesRT from 222
5 May 20267 May 20261 StopFrontier AirlinesRT from 249
6 May 20268 May 20261 StopFrontier AirlinesRT from 298
7 May 202610 May 20261 StopFrontier AirlinesRT from 216
8 May 202613 May 20261 StopFrontier AirlinesRT from 211
9 May 202613 May 20261 StopFrontier AirlinesRT from 225
11 May 202612 May 2026DirectSouthwest AirlinesRT from 239
12 May 20266 June 20261 StopFrontier AirlinesRT from 213
13 May 202615 May 20261 StopFrontier AirlinesRT from 306
14 May 202617 May 20261 StopFrontier AirlinesRT from 244
15 May 202617 May 20261 StopFrontier AirlinesRT from 258
16 May 202618 May 20261 StopFrontier AirlinesRT from 244
17 May 202621 May 2026DirectSouthwest AirlinesRT from 254
18 May 202619 May 20261 StopFrontier AirlinesRT from 285
19 May 202620 May 20261 StopSouthwest AirlinesRT from 168
20 May 20264 June 2026DirectSouthwest AirlinesRT from 181
21 May 20266 June 2026DirectSouthwest AirlinesRT from 200
22 May 20264 June 2026DirectSouthwest AirlinesRT from 247
23 May 202625 May 2026DirectSouthwest AirlinesRT from 223
24 May 202626 May 2026DirectSouthwest AirlinesRT from 228
25 May 20265 June 20261 StopSouthwest AirlinesRT from 240
26 May 20264 June 2026DirectSouthwest AirlinesRT from 200
27 May 202629 May 2026DirectSouthwest AirlinesRT from 205
28 May 202631 May 2026DirectSouthwest AirlinesRT from 197
5 June 20267 June 20261 StopFrontier AirlinesRT from 121
8 June 202610 June 2026DirectSouthwest AirlinesRT from 266
10 June 202612 June 2026DirectSouthwest AirlinesRT from 254
11 June 202615 June 2026DirectSouthwest AirlinesRT from 206
13 June 202614 June 2026DirectSouthwest AirlinesRT from 167
14 June 202616 June 20261 StopFrontier AirlinesRT from 236
15 June 202616 June 2026DirectSouthwest AirlinesRT from 216
20 June 202624 June 2026DirectSouthwest AirlinesRT from 168
25 June 202628 June 20261 StopSouthwest AirlinesRT from 272
26 June 202629 June 2026DirectSouthwest AirlinesRT from 193
20 July 202631 July 2026DirectSouthwest AirlinesRT from 280
9 August 202611 August 2026DirectSouthwest AirlinesRT from 176
13 August 202622 August 2026DirectSouthwest AirlinesRT from 216
14 August 202614 August 2026DirectSouthwest AirlinesRT from 182
28 August 202631 August 2026DirectSouthwest AirlinesRT from 294
16 September 202620 September 20261 StopSouthwest AirlinesRT from 303

The Cheapest Flights from to New York for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
30 April 20263 May 2026DirectFrontier AirlinesRT from 200
19 May 202620 May 20261 StopSouthwest AirlinesRT from 168
5 June 20267 June 20261 StopFrontier AirlinesRT from 121
20 July 202631 July 2026DirectSouthwest AirlinesRT from 280
9 August 202611 August 2026DirectSouthwest AirlinesRT from 176
16 September 202620 September 20261 StopSouthwest AirlinesRT from 303
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