Cheap Flights from NYC to MDW

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The Cheapest Round-trip Tickets from New York to

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27 May 202531 May 2025DirectSouthwest AirlinesRT from 186

The Cheapest Flights for this Month from New York to

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29 April 20252 May 2025DirectSouthwest AirlinesRT from 407
30 April 20253 May 2025DirectSouthwest AirlinesRT from 270
2 May 20257 May 20251 StopFrontier AirlinesRT from 324
4 May 202511 May 20251 StopFrontier AirlinesRT from 307
6 May 202513 May 2025DirectSouthwest AirlinesRT from 291
8 May 202512 May 2025DirectSouthwest AirlinesRT from 270
12 May 202514 May 20251 StopFrontier AirlinesRT from 229
20 May 202512 June 2025DirectSouthwest AirlinesRT from 228
23 May 202525 May 20251 StopSouthwest AirlinesRT from 318
24 May 202514 June 2025DirectSouthwest AirlinesRT from 271
25 May 20255 June 2025DirectSouthwest AirlinesRT from 236
26 May 202527 May 20251 StopSouthwest AirlinesRT from 284
27 May 202531 May 20251 StopSouthwest AirlinesRT from 186
30 May 20253 June 2025DirectSouthwest AirlinesRT from 230
12 June 202514 June 2025DirectSouthwest AirlinesRT from 251
12 July 202514 July 2025DirectSouthwest AirlinesRT from 225
25 July 202531 July 2025DirectSouthwest AirlinesRT from 247

The Cheapest Flights from New York to for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
30 April 20253 May 2025DirectSouthwest AirlinesRT from 270
27 May 202531 May 20251 StopSouthwest AirlinesRT from 186
12 June 202514 June 2025DirectSouthwest AirlinesRT from 251
12 July 202514 July 2025DirectSouthwest AirlinesRT from 225
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