Cheap Flights from NYC to CHI

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The Cheapest Round-trip Tickets from New York to Chicago

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18 April 202622 April 2026DirectSpirit AirlinesRT from 77

The Cheapest Flights for this Month from New York to Chicago

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1 April 20268 April 2026DirectUnited AirlinesRT from 193
2 April 20265 April 20261 StopSpirit AirlinesRT from 220
3 April 20265 April 20261 StopSpirit AirlinesRT from 228
5 April 202619 April 20261 StopFrontier AirlinesRT from 125
6 April 20268 April 2026DirectAmerican AirlinesRT from 215
7 April 202621 April 2026DirectSpirit AirlinesRT from 89
8 April 202612 April 20261 StopSpirit AirlinesRT from 200
9 April 202615 April 2026DirectSpirit AirlinesRT from 115
10 April 202612 April 2026DirectSpirit AirlinesRT from 184
12 April 202612 April 2026DirectSpirit AirlinesRT from 288
13 April 202614 April 2026DirectSpirit AirlinesRT from 85
16 April 202619 April 2026DirectSpirit AirlinesRT from 158
18 April 202622 April 2026DirectSpirit AirlinesRT from 77
20 April 202623 April 2026DirectFrontier AirlinesRT from 130
22 April 202625 April 2026DirectFrontier AirlinesRT from 87
23 April 202626 April 2026DirectFrontier AirlinesRT from 120
24 April 202626 April 2026DirectSpirit AirlinesRT from 109
25 April 202626 April 2026DirectFrontier AirlinesRT from 92
29 April 20261 May 2026DirectSpirit AirlinesRT from 109
30 April 20264 May 2026DirectSpirit AirlinesRT from 127
8 May 202614 May 2026DirectSpirit AirlinesRT from 114
18 May 20261 June 20261 StopSouthwest AirlinesRT from 186
3 June 202610 June 20261 StopSpirit AirlinesRT from 138
5 June 202612 June 2026DirectJetBlue AirwaysRT from 180
12 August 202615 August 2026DirectAmerican AirlinesRT from 190

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

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18 April 202622 April 2026DirectSpirit AirlinesRT from 77
8 May 202614 May 2026DirectSpirit AirlinesRT from 114
3 June 202610 June 20261 StopSpirit AirlinesRT from 138
12 August 202615 August 2026DirectAmerican AirlinesRT from 190
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