Cheap Flights from NYC to MDW

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The Cheapest Round-trip Tickets from New York to

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10 March 202612 March 2026DirectFrontier AirlinesRT from 48

The Cheapest Flights for this Month from New York to

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15 February 202628 February 2026DirectSouthwest AirlinesRT from 331
16 February 202616 February 2026DirectSouthwest AirlinesRT from 455
17 February 202619 February 20261 StopFrontier AirlinesRT from 365
18 February 202620 February 20261 StopFrontier AirlinesRT from 341
19 February 202620 February 2026DirectSouthwest AirlinesRT from 303
20 February 202623 February 20261 StopFrontier AirlinesRT from 213
21 February 202622 February 2026DirectSouthwest AirlinesRT from 324
22 February 202624 February 2026DirectSouthwest AirlinesRT from 157
26 February 202628 February 20261 StopFrontier AirlinesRT from 187
27 February 20261 March 2026DirectSouthwest AirlinesRT from 174
10 March 202612 March 2026DirectFrontier AirlinesRT from 48
12 March 202615 March 20261 StopFrontier AirlinesRT from 209
13 March 202615 March 20261 StopFrontier AirlinesRT from 262
17 March 202619 March 2026DirectFrontier AirlinesRT from 98
27 March 202629 March 2026DirectSouthwest AirlinesRT from 174
1 April 20269 April 20261 StopSouthwest AirlinesRT from 184
3 April 20266 April 2026DirectSouthwest AirlinesRT from 199
8 April 202612 April 2026DirectSouthwest AirlinesRT from 161
17 April 202619 May 2026DirectFrontier AirlinesRT from 83
20 April 20264 May 2026DirectFrontier AirlinesRT from 82
23 April 202628 April 2026DirectFrontier AirlinesRT from 72
4 May 202618 May 2026DirectFrontier AirlinesRT from 130
6 May 20268 May 2026DirectFrontier AirlinesRT from 98
7 May 20268 May 2026DirectFrontier AirlinesRT from 98
8 May 202610 May 2026DirectFrontier AirlinesRT from 110
12 May 202615 May 2026DirectFrontier AirlinesRT from 55
13 May 202615 May 2026DirectFrontier AirlinesRT from 57
26 May 202628 May 2026DirectSouthwest AirlinesRT from 205
2 June 20269 June 2026DirectSouthwest AirlinesRT from 145
4 June 20268 June 2026DirectSouthwest AirlinesRT from 145
5 June 20265 June 2026DirectSouthwest AirlinesRT from 305
23 June 202630 June 2026DirectSouthwest AirlinesRT from 266
25 June 202628 June 2026DirectSouthwest AirlinesRT from 310
30 June 202630 June 2026DirectSouthwest AirlinesRT from 282
10 July 202611 July 2026DirectSouthwest AirlinesRT from 315
24 July 202626 July 2026DirectSouthwest AirlinesRT from 356
25 August 20269 September 2026DirectSouthwest AirlinesRT from 284
11 September 202612 September 2026DirectSouthwest AirlinesRT from 345
6 November 202610 November 20262 StopsPorter AirlinesRT from 745

The Cheapest Flights from New York to for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
22 February 202624 February 2026DirectSouthwest AirlinesRT from 157
10 March 202612 March 2026DirectFrontier AirlinesRT from 48
23 April 202628 April 2026DirectFrontier AirlinesRT from 72
12 May 202615 May 2026DirectFrontier AirlinesRT from 55
4 June 20268 June 2026DirectSouthwest AirlinesRT from 145
10 July 202611 July 2026DirectSouthwest AirlinesRT from 315
25 August 20269 September 2026DirectSouthwest AirlinesRT from 284
11 September 202612 September 2026DirectSouthwest AirlinesRT from 345
6 November 202610 November 20262 StopsPorter AirlinesRT from 745
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