Cheap Flights from NYC to MDW

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The Cheapest Round-trip Tickets from New York to

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14 April 202615 April 2026DirectFrontier AirlinesRT from 69

The Cheapest Flights for this Month from New York to

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19 March 202627 March 2026DirectFrontier AirlinesRT from 234
20 March 202622 March 20261 StopFrontier AirlinesRT from 313
21 March 202623 March 20261 StopFrontier AirlinesRT from 300
23 March 202626 March 2026DirectSouthwest AirlinesRT from 284
31 March 20268 April 20261 StopFrontier AirlinesRT from 199
1 April 20266 April 2026DirectSouthwest AirlinesRT from 336
3 April 20264 April 20261 StopSouthwest AirlinesRT from 244
4 April 202611 April 2026DirectSouthwest AirlinesRT from 275
5 April 202611 April 20261 StopSouthwest AirlinesRT from 301
6 April 202611 April 20261 StopSouthwest AirlinesRT from 215
7 April 202613 April 20261 StopSouthwest AirlinesRT from 200
8 April 202611 April 2026DirectSouthwest AirlinesRT from 179
9 April 202612 April 2026DirectSouthwest AirlinesRT from 227
12 April 202614 April 2026DirectSouthwest AirlinesRT from 213
13 April 202614 April 2026DirectSouthwest AirlinesRT from 123
14 April 202615 April 2026DirectFrontier AirlinesRT from 69
17 April 202620 April 2026DirectFrontier AirlinesRT from 110
23 April 202628 April 2026DirectFrontier AirlinesRT from 102
6 May 20268 May 20261 StopFrontier AirlinesRT from 177
8 May 202610 May 2026DirectSouthwest AirlinesRT from 184
10 May 202613 May 2026DirectSouthwest AirlinesRT from 194
11 May 202617 May 2026DirectSouthwest AirlinesRT from 190
15 May 202618 May 20261 StopSouthwest AirlinesRT from 220
17 May 202620 May 2026DirectSouthwest AirlinesRT from 212
1 June 20269 June 2026DirectSouthwest AirlinesRT from 182
5 June 20267 June 20261 StopSouthwest AirlinesRT from 201
7 June 20269 June 2026DirectSouthwest AirlinesRT from 326
9 June 202611 June 2026DirectSouthwest AirlinesRT from 221
26 June 20263 July 2026DirectSouthwest AirlinesRT from 470
28 June 20264 July 2026DirectSouthwest AirlinesRT from 541
24 July 202621 August 2026DirectSouthwest AirlinesRT from 356
31 July 20262 August 20261 StopFrontier AirlinesRT from 250
6 September 202613 September 2026DirectSouthwest AirlinesRT from 360

The Cheapest Flights from New York to for the Year Ahead

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31 March 20268 April 20261 StopFrontier AirlinesRT from 199
14 April 202615 April 2026DirectFrontier AirlinesRT from 69
6 May 20268 May 20261 StopFrontier AirlinesRT from 177
1 June 20269 June 2026DirectSouthwest AirlinesRT from 182
31 July 20262 August 20261 StopFrontier AirlinesRT from 250
6 September 202613 September 2026DirectSouthwest AirlinesRT from 360
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