Cheap Flights from MDW to NYC

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The Cheapest Round-trip Tickets from to New York

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19 March 202624 March 2026DirectFrontier AirlinesRT from 60

The Cheapest Flights for this Month from to New York

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22 February 202623 March 2026DirectSouthwest AirlinesRT from 395
23 February 202624 March 20261 StopFrontier AirlinesRT from 198
27 February 20262 March 2026DirectSouthwest AirlinesRT from 216
1 March 20268 March 20261 StopFrontier AirlinesRT from 213
4 March 202610 March 20261 StopFrontier AirlinesRT from 115
6 March 20268 March 2026DirectSouthwest AirlinesRT from 171
7 March 202619 April 2026DirectSouthwest AirlinesRT from 176
8 March 202614 March 20261 StopFrontier AirlinesRT from 184
9 March 202616 March 2026DirectSouthwest AirlinesRT from 136
10 March 202615 March 2026DirectFrontier AirlinesRT from 86
12 March 202618 March 20261 StopFrontier AirlinesRT from 97
13 March 202615 March 20261 StopFrontier AirlinesRT from 204
15 March 202619 March 20261 StopFrontier AirlinesRT from 133
17 March 202620 March 2026DirectSouthwest AirlinesRT from 169
19 March 202624 March 2026DirectFrontier AirlinesRT from 60
20 March 202627 March 2026DirectSouthwest AirlinesRT from 268
21 March 202624 March 2026DirectSouthwest AirlinesRT from 231
25 March 202625 March 2026DirectSouthwest AirlinesRT from 176
27 March 202631 March 2026DirectSouthwest AirlinesRT from 192
28 March 202628 March 2026DirectSouthwest AirlinesRT from 434
31 March 202630 May 2026DirectFrontier AirlinesRT from 146
6 April 20267 April 2026DirectSouthwest AirlinesRT from 150
16 April 202620 April 2026DirectFrontier AirlinesRT from 99
17 April 202619 April 2026DirectFrontier AirlinesRT from 130
19 April 202621 April 2026DirectFrontier AirlinesRT from 81
1 May 20263 May 20261 StopFrontier AirlinesRT from 161
7 May 202611 May 2026DirectFrontier AirlinesRT from 81
17 May 202618 May 2026DirectFrontier AirlinesRT from 172
8 July 202612 July 2026DirectSouthwest AirlinesRT from 369
22 July 202625 July 2026DirectSouthwest AirlinesRT from 148
22 October 202626 October 2026DirectSouthwest AirlinesRT from 287

The Cheapest Flights from to New York for the Year Ahead

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23 February 202624 March 20261 StopFrontier AirlinesRT from 198
19 March 202624 March 2026DirectFrontier AirlinesRT from 60
19 April 202621 April 2026DirectFrontier AirlinesRT from 81
7 May 202611 May 2026DirectFrontier AirlinesRT from 81
22 July 202625 July 2026DirectSouthwest AirlinesRT from 148
22 October 202626 October 2026DirectSouthwest AirlinesRT from 287
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