Cheap Flights from NYC to MDW

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The Cheapest Round-trip Tickets from New York to

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4 February 202511 February 2025DirectFrontier AirlinesRT from 113

The Cheapest Flights for this Month from New York to

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29 December 20242 January 20251 StopSouthwest AirlinesRT from 380
30 December 20241 January 2025DirectSouthwest AirlinesRT from 449
31 December 20245 January 2025DirectSouthwest AirlinesRT from 215
1 January 20255 January 2025DirectSouthwest AirlinesRT from 215
2 January 20252 January 20251 StopSouthwest AirlinesRT from 380
15 January 202517 January 2025DirectSouthwest AirlinesRT from 168
22 January 202531 January 2025DirectSouthwest AirlinesRT from 167
31 January 202510 February 2025DirectSouthwest AirlinesRT from 204
1 February 20255 February 2025DirectSouthwest AirlinesRT from 169
3 February 20259 February 2025DirectSouthwest AirlinesRT from 186
4 February 202511 February 20251 StopFrontier AirlinesRT from 113
17 March 202519 March 2025DirectSouthwest AirlinesRT from 206

The Cheapest Flights from New York to for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
31 December 20245 January 2025DirectSouthwest AirlinesRT from 215
22 January 202531 January 2025DirectSouthwest AirlinesRT from 167
4 February 202511 February 20251 StopFrontier AirlinesRT from 113
17 March 202519 March 2025DirectSouthwest AirlinesRT from 206
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