Cheap Flights from NYC to MDW

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The Cheapest Round-trip Tickets from New York to

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24 August 202628 August 2026DirectSouthwest AirlinesRT from 158

The Cheapest Flights for this Month from New York to

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16 July 202617 July 2026DirectSouthwest AirlinesRT from 557
17 July 202619 July 20261 StopSouthwest AirlinesRT from 480
18 July 202621 July 2026DirectSouthwest AirlinesRT from 364
19 July 202622 July 20261 StopFrontier AirlinesRT from 313
20 July 202623 July 20261 StopFrontier AirlinesRT from 372
21 July 202623 July 20261 StopFrontier AirlinesRT from 300
22 July 202629 July 2026DirectSouthwest AirlinesRT from 260
24 July 202629 July 20261 StopFrontier AirlinesRT from 293
25 July 20267 August 2026DirectSouthwest AirlinesRT from 291
28 July 20266 August 2026DirectSouthwest AirlinesRT from 285
29 July 20268 August 20261 StopSouthwest AirlinesRT from 342
30 July 20268 August 20261 StopFrontier AirlinesRT from 237
31 July 20266 August 20261 StopSouthwest AirlinesRT from 294
1 August 202625 August 2026DirectSouthwest AirlinesRT from 262
4 August 202614 August 2026DirectSouthwest AirlinesRT from 217
5 August 202615 August 2026DirectSouthwest AirlinesRT from 217
7 August 202615 August 20261 StopSouthwest AirlinesRT from 246
11 August 202618 August 2026DirectSouthwest AirlinesRT from 190
12 August 202619 August 2026DirectSouthwest AirlinesRT from 192
13 August 202616 August 20261 StopSouthwest AirlinesRT from 206
14 August 202616 August 20261 StopSouthwest AirlinesRT from 236
15 August 202622 August 20261 StopFrontier AirlinesRT from 249
24 August 202628 August 2026DirectSouthwest AirlinesRT from 158
27 August 202631 August 2026DirectSouthwest AirlinesRT from 217
30 August 20262 September 2026DirectSouthwest AirlinesRT from 216
4 September 20266 September 20261 StopSouthwest AirlinesRT from 239
5 September 20266 September 2026DirectSouthwest AirlinesRT from 218
10 September 202614 September 2026DirectSouthwest AirlinesRT from 217
12 September 202616 September 2026DirectSouthwest AirlinesRT from 189
17 September 202621 September 2026DirectSouthwest AirlinesRT from 207
3 October 202610 October 20261 StopSouthwest AirlinesRT from 237
6 October 202613 October 2026DirectSouthwest AirlinesRT from 216
8 October 202610 October 20261 StopSouthwest AirlinesRT from 210
9 October 202612 October 20261 StopSouthwest AirlinesRT from 303
5 November 20265 November 2026DirectSouthwest AirlinesRT from 222
29 December 20266 January 2027DirectSouthwest AirlinesRT from 315

The Cheapest Flights from New York to for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
30 July 20268 August 20261 StopFrontier AirlinesRT from 237
24 August 202628 August 2026DirectSouthwest AirlinesRT from 158
12 September 202616 September 2026DirectSouthwest AirlinesRT from 189
8 October 202610 October 20261 StopSouthwest AirlinesRT from 210
5 November 20265 November 2026DirectSouthwest AirlinesRT from 222
29 December 20266 January 2027DirectSouthwest AirlinesRT from 315
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