Cheap Flights from NYC to MDW

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The Cheapest Round-trip Tickets from New York to

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30 April 20263 May 2026DirectFrontier AirlinesRT from 113

The Cheapest Flights for this Month from New York to

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21 April 202628 April 20261 StopFrontier AirlinesRT from 208
22 April 202625 April 2026DirectFrontier AirlinesRT from 193
23 April 202624 April 20261 StopFrontier AirlinesRT from 194
24 April 202627 April 2026DirectFrontier AirlinesRT from 173
26 April 20261 May 2026DirectFrontier AirlinesRT from 150
27 April 20262 May 2026DirectFrontier AirlinesRT from 145
30 April 20263 May 2026DirectFrontier AirlinesRT from 113
1 May 20263 May 2026DirectFrontier AirlinesRT from 189
2 May 20265 May 20261 StopFrontier AirlinesRT from 196
5 May 20267 May 2026DirectSouthwest AirlinesRT from 204
6 May 20268 May 20261 StopFrontier AirlinesRT from 207
7 May 202610 May 2026DirectSouthwest AirlinesRT from 259
8 May 202611 May 2026DirectSouthwest AirlinesRT from 185
12 May 202622 May 2026DirectSouthwest AirlinesRT from 256
15 May 202618 May 20261 StopFrontier AirlinesRT from 256
16 May 202618 May 2026DirectSouthwest AirlinesRT from 295
17 May 202617 May 2026DirectSouthwest AirlinesRT from 455
22 May 202622 May 2026DirectSouthwest AirlinesRT from 222
27 May 202630 May 20261 StopFrontier AirlinesRT from 172
29 May 202631 May 2026DirectSouthwest AirlinesRT from 196
11 June 202614 June 2026DirectSouthwest AirlinesRT from 164
23 June 202625 June 2026DirectSouthwest AirlinesRT from 183
7 July 202611 July 2026DirectSouthwest AirlinesRT from 219
27 July 202630 July 2026DirectSouthwest AirlinesRT from 347
29 July 202613 August 2026DirectSouthwest AirlinesRT from 216
30 July 20262 August 2026DirectSouthwest AirlinesRT from 238
2 August 20269 August 2026DirectSouthwest AirlinesRT from 257
11 September 202612 September 2026DirectSouthwest AirlinesRT from 324
18 September 202620 September 2026DirectSouthwest AirlinesRT from 608

The Cheapest Flights from New York to for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
30 April 20263 May 2026DirectFrontier AirlinesRT from 113
27 May 202630 May 20261 StopFrontier AirlinesRT from 172
11 June 202614 June 2026DirectSouthwest AirlinesRT from 164
29 July 202613 August 2026DirectSouthwest AirlinesRT from 216
2 August 20269 August 2026DirectSouthwest AirlinesRT from 257
11 September 202612 September 2026DirectSouthwest AirlinesRT from 324
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