Cheap Flights from MDW to NYC

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The Cheapest Round-trip Tickets from to New York

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11 November 202514 November 2025DirectFrontier AirlinesRT from 142

The Cheapest Flights for this Month from to New York

Departure atReturn atStopsAirlineFind tickets
31 October 20252 November 2025DirectSouthwest AirlinesRT from 227
7 November 202511 November 20251 StopFrontier AirlinesRT from 206
11 November 202514 November 2025DirectFrontier AirlinesRT from 142
21 November 202523 November 2025DirectSouthwest AirlinesRT from 247
3 December 20256 December 20251 StopSouthwest AirlinesRT from 235
20 December 202522 December 2025DirectSouthwest AirlinesRT from 490
15 February 202618 February 2026DirectSouthwest AirlinesRT from 262
19 March 202622 March 2026DirectFrontier AirlinesRT from 316

The Cheapest Flights from to New York for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
31 October 20252 November 2025DirectSouthwest AirlinesRT from 227
11 November 202514 November 2025DirectFrontier AirlinesRT from 142
3 December 20256 December 20251 StopSouthwest AirlinesRT from 235
15 February 202618 February 2026DirectSouthwest AirlinesRT from 262
19 March 202622 March 2026DirectFrontier AirlinesRT from 316
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