Cheap Flights from NYC to MDW

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The Cheapest Round-trip Tickets from New York to

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29 September 20253 October 2025DirectFrontier AirlinesRT from 161

The Cheapest Flights for this Month from New York to

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4 September 20256 September 20251 StopFrontier AirlinesRT from 256
5 September 20256 September 20251 StopFrontier AirlinesRT from 188
8 September 20259 September 2025DirectSouthwest AirlinesRT from 333
11 September 202513 September 20251 StopFrontier AirlinesRT from 165
13 September 202516 September 2025DirectSouthwest AirlinesRT from 267
17 September 202524 September 20251 StopSouthwest AirlinesRT from 212
22 September 202525 September 20251 StopFrontier AirlinesRT from 163
26 September 202529 September 20251 StopFrontier AirlinesRT from 171
29 September 20253 October 20251 StopFrontier AirlinesRT from 161
1 October 20253 October 20251 StopFrontier AirlinesRT from 168
3 October 202513 October 20251 StopFrontier AirlinesRT from 209
6 October 202512 October 2025DirectSouthwest AirlinesRT from 298
8 October 202510 October 20251 StopFrontier AirlinesRT from 183
18 October 202519 October 20251 StopFrontier AirlinesRT from 268
23 October 202526 October 2025DirectFrontier AirlinesRT from 203
25 October 202527 October 20251 StopFrontier AirlinesRT from 188
6 November 20258 November 20251 StopFrontier AirlinesRT from 196
7 November 20259 November 20251 StopFrontier AirlinesRT from 176
22 November 202526 November 2025DirectSouthwest AirlinesRT from 262
26 December 202510 January 2026DirectSouthwest AirlinesRT from 312
27 December 202512 January 2026DirectSouthwest AirlinesRT from 312
28 December 202511 January 2026DirectSouthwest AirlinesRT from 365
29 December 202510 January 2026DirectSouthwest AirlinesRT from 296
30 April 20264 May 2026DirectSouthwest AirlinesRT from 344

The Cheapest Flights from New York to for the Year Ahead

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29 September 20253 October 20251 StopFrontier AirlinesRT from 161
1 October 20253 October 20251 StopFrontier AirlinesRT from 168
7 November 20259 November 20251 StopFrontier AirlinesRT from 176
29 December 202510 January 2026DirectSouthwest AirlinesRT from 296
30 April 20264 May 2026DirectSouthwest AirlinesRT from 344
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