Cheap Flights from CHI to NYC

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The Cheapest Round-trip Tickets from Chicago to New York

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29 September 20266 October 2026DirectSouthwest AirlinesRT from 155

The Cheapest Flights for this Month from Chicago to New York

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1 July 202611 July 2026DirectUnited AirlinesRT from 267
2 July 20266 July 2026DirectUnited AirlinesRT from 298
3 July 20267 July 20261 StopFrontier AirlinesRT from 268
4 July 20265 July 20261 StopFrontier AirlinesRT from 267
6 July 20269 July 20261 StopFrontier AirlinesRT from 292
10 July 202612 July 2026DirectUnited AirlinesRT from 276
12 July 202615 July 20261 StopAmerican AirlinesRT from 253
13 July 202615 July 20261 StopAmerican AirlinesRT from 226
14 July 202617 July 2026DirectUnited AirlinesRT from 235
15 July 202625 July 2026DirectjetBlueRT from 207
17 July 202619 July 2026DirectjetBlueRT from 227
18 July 20267 August 2026DirectSouthwest AirlinesRT from 220
21 July 202624 July 2026DirectUnited AirlinesRT from 211
24 July 202626 July 2026DirectjetBlueRT from 205
25 July 202628 July 2026DirectUnited AirlinesRT from 182
26 July 202631 July 20261 StopSouthwest AirlinesRT from 282
1 August 20265 August 2026DirectUnited AirlinesRT from 169
4 August 20267 August 2026DirectSouthwest AirlinesRT from 196
6 August 20269 August 2026DirectjetBlueRT from 213
7 August 202610 August 2026DirectjetBlueRT from 198
11 August 202613 August 2026DirectjetBlueRT from 180
23 August 202613 September 2026DirectSouthwest AirlinesRT from 191
29 September 20266 October 2026DirectSouthwest AirlinesRT from 155
3 October 20268 October 2026DirectAmerican AirlinesRT from 235
23 December 202627 December 2026DirectAmerican AirlinesRT from 305

The Cheapest Flights from Chicago to New York for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
25 July 202628 July 2026DirectUnited AirlinesRT from 182
1 August 20265 August 2026DirectUnited AirlinesRT from 169
29 September 20266 October 2026DirectSouthwest AirlinesRT from 155
3 October 20268 October 2026DirectAmerican AirlinesRT from 235
23 December 202627 December 2026DirectAmerican AirlinesRT from 305
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