Cheap Flights from NYC to MDW

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The Cheapest Round-trip Tickets from New York to

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10 July 202613 July 2026DirectSouthwest AirlinesRT from 123

The Cheapest Flights for this Month from New York to

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30 April 202612 May 2026DirectFrontier AirlinesRT from 170
1 May 20265 May 20261 StopFrontier AirlinesRT from 277
2 May 20263 May 2026DirectFrontier AirlinesRT from 312
5 May 20266 May 20261 StopFrontier AirlinesRT from 287
6 May 20267 May 20261 StopFrontier AirlinesRT from 231
7 May 20267 May 2026DirectSouthwest AirlinesRT from 281
8 May 202611 May 20261 StopFrontier AirlinesRT from 365
11 May 202615 May 20261 StopFrontier AirlinesRT from 280
16 May 202616 May 2026DirectSouthwest AirlinesRT from 244
20 May 202623 May 2026DirectSouthwest AirlinesRT from 130
22 May 202624 May 2026DirectSouthwest AirlinesRT from 286
24 May 202626 May 2026DirectSouthwest AirlinesRT from 223
28 May 20261 June 20261 StopFrontier AirlinesRT from 196
29 May 20266 June 2026DirectSouthwest AirlinesRT from 204
4 June 20267 June 2026DirectSouthwest AirlinesRT from 272
1 July 20265 July 2026DirectSouthwest AirlinesRT from 160
10 July 202613 July 20261 StopSouthwest AirlinesRT from 123
11 July 202612 July 2026DirectSouthwest AirlinesRT from 185
22 July 20262 August 2026DirectSouthwest AirlinesRT from 239
23 July 20262 August 2026DirectSouthwest AirlinesRT from 238
14 September 202618 September 2026DirectSouthwest AirlinesRT from 303
15 September 202618 September 2026DirectSouthwest AirlinesRT from 278
9 October 202612 October 20261 StopSouthwest AirlinesRT from 384
1 November 20268 November 20261 StopSouthwest AirlinesRT from 395
4 November 202611 November 2026DirectSouthwest AirlinesRT from 297
15 November 202622 November 2026DirectSouthwest AirlinesRT from 420

The Cheapest Flights from New York to for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
30 April 202612 May 2026DirectFrontier AirlinesRT from 170
20 May 202623 May 2026DirectSouthwest AirlinesRT from 130
4 June 20267 June 2026DirectSouthwest AirlinesRT from 272
10 July 202613 July 20261 StopSouthwest AirlinesRT from 123
15 September 202618 September 2026DirectSouthwest AirlinesRT from 278
9 October 202612 October 20261 StopSouthwest AirlinesRT from 384
4 November 202611 November 2026DirectSouthwest AirlinesRT from 297
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