Cheap Flights from NYC to MDW

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The Cheapest Round-trip Tickets from New York to

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18 July 202618 July 2026DirectSouthwest AirlinesRT from 151

The Cheapest Flights for this Month from New York to

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2 July 20264 July 2026DirectSouthwest AirlinesRT from 456
3 July 20266 July 2026DirectSouthwest AirlinesRT from 480
4 July 20266 July 2026DirectSouthwest AirlinesRT from 416
5 July 20269 July 20261 StopFrontier AirlinesRT from 379
7 July 20269 July 20261 StopFrontier AirlinesRT from 358
8 July 202610 July 20261 StopFrontier AirlinesRT from 292
9 July 202610 July 20261 StopFrontier AirlinesRT from 283
10 July 202612 July 2026DirectSouthwest AirlinesRT from 355
13 July 202617 July 20261 StopFrontier AirlinesRT from 314
14 July 202617 July 2026DirectSouthwest AirlinesRT from 248
16 July 202618 July 2026DirectSouthwest AirlinesRT from 209
18 July 202618 July 20261 StopSouthwest AirlinesRT from 151
19 July 202621 July 2026DirectSouthwest AirlinesRT from 199
20 July 202622 July 2026DirectSouthwest AirlinesRT from 220
22 July 202629 July 2026DirectSouthwest AirlinesRT from 154
25 July 202629 July 2026DirectSouthwest AirlinesRT from 188
28 July 20261 August 2026DirectSouthwest AirlinesRT from 183
29 July 20263 August 20261 StopSouthwest AirlinesRT from 334
31 July 20263 August 2026DirectSouthwest AirlinesRT from 414
5 August 20267 August 2026DirectSouthwest AirlinesRT from 196
11 August 202613 August 2026DirectSouthwest AirlinesRT from 179
12 August 202616 August 2026DirectSouthwest AirlinesRT from 196
13 August 202613 August 2026DirectSouthwest AirlinesRT from 198
15 August 202616 August 2026DirectSouthwest AirlinesRT from 185
17 August 202620 August 2026DirectSouthwest AirlinesRT from 197
19 August 202620 August 2026DirectSouthwest AirlinesRT from 174
27 August 202630 August 2026DirectSouthwest AirlinesRT from 203
1 September 202610 September 2026DirectSouthwest AirlinesRT from 209
4 September 20265 September 2026DirectSouthwest AirlinesRT from 240
7 September 202620 October 2026DirectSouthwest AirlinesRT from 262
10 September 202614 September 2026DirectSouthwest AirlinesRT from 184
27 September 20267 October 2026DirectSouthwest AirlinesRT from 153
4 October 20266 October 2026DirectSouthwest AirlinesRT from 183
4 November 202611 November 2026DirectSouthwest AirlinesRT from 245

The Cheapest Flights from New York to for the Year Ahead

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18 July 202618 July 20261 StopSouthwest AirlinesRT from 151
19 August 202620 August 2026DirectSouthwest AirlinesRT from 174
27 September 20267 October 2026DirectSouthwest AirlinesRT from 153
4 October 20266 October 2026DirectSouthwest AirlinesRT from 183
4 November 202611 November 2026DirectSouthwest AirlinesRT from 245
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