Cheap Flights from MDW to NYC

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The Cheapest Round-trip Tickets from to New York

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14 January 202621 January 2026DirectSouthwest AirlinesRT from 96

The Cheapest Flights for this Month from to New York

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1 January 20263 January 20261 StopSouthwest AirlinesRT from 456
5 January 202612 January 2026DirectSouthwest AirlinesRT from 251
9 January 202616 January 2026DirectSouthwest AirlinesRT from 173
10 January 202617 January 2026DirectSouthwest AirlinesRT from 218
11 January 202613 January 2026DirectSouthwest AirlinesRT from 181
12 January 202614 January 2026DirectSouthwest AirlinesRT from 173
14 January 202621 January 2026DirectSouthwest AirlinesRT from 96
17 January 202621 January 2026DirectSouthwest AirlinesRT from 111
23 January 202630 January 2026DirectSouthwest AirlinesRT from 109
10 February 202615 February 2026DirectSouthwest AirlinesRT from 144
13 February 202620 February 2026DirectSouthwest AirlinesRT from 135
13 April 202620 April 2026DirectSouthwest AirlinesRT from 208
16 April 202620 April 2026DirectSouthwest AirlinesRT from 217
20 April 202620 April 2026DirectSouthwest AirlinesRT from 248

The Cheapest Flights from to New York for the Year Ahead

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14 January 202621 January 2026DirectSouthwest AirlinesRT from 96
13 February 202620 February 2026DirectSouthwest AirlinesRT from 135
13 April 202620 April 2026DirectSouthwest AirlinesRT from 208
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