Cheap Flights from NYC to MDW

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The Cheapest Round-trip Tickets from New York to

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9 December 202510 December 2025DirectFrontier AirlinesRT from 109

The Cheapest Flights for this Month from New York to

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7 December 20258 December 20251 StopFrontier AirlinesRT from 263
8 December 20259 December 2025DirectSouthwest AirlinesRT from 223
9 December 202510 December 20251 StopFrontier AirlinesRT from 109
10 December 202510 December 2025DirectSouthwest AirlinesRT from 270
13 December 202514 December 2025DirectSouthwest AirlinesRT from 225
14 December 202516 December 2025DirectFrontier AirlinesRT from 126
28 December 202519 January 2026DirectFrontier AirlinesRT from 274
29 December 202519 January 2026DirectSouthwest AirlinesRT from 290
1 January 20264 January 2026DirectFrontier AirlinesRT from 145
2 January 20266 January 2026DirectSouthwest AirlinesRT from 260
11 January 202612 January 2026DirectSouthwest AirlinesRT from 143
12 January 202618 January 2026DirectSouthwest AirlinesRT from 122
18 January 202619 January 20261 StopFrontier AirlinesRT from 118
9 March 202611 March 2026DirectSouthwest AirlinesRT from 246
27 March 202629 March 2026DirectSouthwest AirlinesRT from 276
15 April 202622 April 2026DirectSouthwest AirlinesRT from 250
23 April 202628 April 2026DirectSouthwest AirlinesRT from 268
5 June 20268 June 2026DirectSouthwest AirlinesRT from 373
14 July 202618 July 2026DirectSouthwest AirlinesRT from 328

The Cheapest Flights from New York to for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
9 December 202510 December 20251 StopFrontier AirlinesRT from 109
18 January 202619 January 20261 StopFrontier AirlinesRT from 118
9 March 202611 March 2026DirectSouthwest AirlinesRT from 246
15 April 202622 April 2026DirectSouthwest AirlinesRT from 250
5 June 20268 June 2026DirectSouthwest AirlinesRT from 373
14 July 202618 July 2026DirectSouthwest AirlinesRT from 328
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