Cheap Flights from NYC to MDW

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The Cheapest Round-trip Tickets from New York to

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1 February 20263 February 2026DirectFrontier AirlinesRT from 131

The Cheapest Flights for this Month from New York to

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17 December 202519 December 2025DirectSouthwest AirlinesRT from 361
23 December 202525 December 2025DirectFrontier AirlinesRT from 261
27 December 20252 January 2026DirectSouthwest AirlinesRT from 427
28 December 202529 December 2025DirectFrontier AirlinesRT from 406
29 December 20255 January 2026DirectSouthwest AirlinesRT from 285
31 December 202510 January 2026DirectSouthwest AirlinesRT from 191
9 January 202611 January 2026DirectSouthwest AirlinesRT from 180
1 February 20263 February 20261 StopFrontier AirlinesRT from 131
6 March 20268 March 2026DirectSouthwest AirlinesRT from 202
23 April 202628 April 2026DirectSouthwest AirlinesRT from 262
28 July 202631 July 2026DirectSouthwest AirlinesRT from 350

The Cheapest Flights from New York to for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
31 December 202510 January 2026DirectSouthwest AirlinesRT from 191
9 January 202611 January 2026DirectSouthwest AirlinesRT from 180
1 February 20263 February 20261 StopFrontier AirlinesRT from 131
6 March 20268 March 2026DirectSouthwest AirlinesRT from 202
23 April 202628 April 2026DirectSouthwest AirlinesRT from 262
28 July 202631 July 2026DirectSouthwest AirlinesRT from 350
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