Cheap Flights from NYC to CHI

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The Cheapest Round-trip Tickets from New York to Chicago

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11 June 202615 June 2026DirectSpirit AirlinesRT from 101

The Cheapest Flights for this Month from New York to Chicago

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20 April 202624 April 20261 StopSpirit AirlinesRT from 289
21 April 202628 April 2026DirectFrontier AirlinesRT from 168
22 April 202625 April 2026DirectFrontier AirlinesRT from 193
24 April 202627 April 20261 StopSpirit AirlinesRT from 147
26 April 20261 May 2026DirectSpirit AirlinesRT from 146
27 April 20262 May 2026DirectFrontier AirlinesRT from 145
30 April 20263 May 2026DirectFrontier AirlinesRT from 113
1 May 20263 May 2026DirectFrontier AirlinesRT from 189
2 May 20265 May 2026DirectSpirit AirlinesRT from 113
5 May 20267 May 2026DirectSpirit AirlinesRT from 127
6 May 20268 May 2026DirectSpirit AirlinesRT from 128
7 May 202610 May 20261 StopSpirit AirlinesRT from 157
8 May 202611 May 20261 StopSpirit AirlinesRT from 145
12 May 202622 May 20261 StopSpirit AirlinesRT from 165
15 May 202618 May 20261 StopSpirit AirlinesRT from 186
16 May 202618 May 20261 StopSpirit AirlinesRT from 186
17 May 202617 May 2026DirectAmerican AirlinesRT from 224
22 May 202622 May 2026DirectUnited AirlinesRT from 162
27 May 202629 May 20261 StopFrontier AirlinesRT from 143
29 May 202631 May 20261 StopSpirit AirlinesRT from 156
11 June 202615 June 2026DirectSpirit AirlinesRT from 101
23 June 202625 June 2026DirectSpirit AirlinesRT from 106
7 July 202611 July 2026DirectSpirit AirlinesRT from 136
27 July 202630 July 2026DirectAmerican AirlinesRT from 186
29 July 202613 August 2026DirectSpirit AirlinesRT from 157
30 July 20262 August 2026DirectSouthwest AirlinesRT from 238
2 August 20269 August 2026DirectAmerican AirlinesRT from 183
11 September 202612 September 2026DirectAmerican AirlinesRT from 180
18 September 202620 September 2026DirectAmerican AirlinesRT from 200
4 November 202611 November 2026DirectSpirit AirlinesRT from 138
6 November 202610 November 2026DirectSpirit AirlinesRT from 201
7 November 202611 November 2026DirectSpirit AirlinesRT from 144
15 November 202622 November 2026DirectAmerican AirlinesRT from 203

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

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30 April 20263 May 2026DirectFrontier AirlinesRT from 113
2 May 20265 May 2026DirectSpirit AirlinesRT from 113
11 June 202615 June 2026DirectSpirit AirlinesRT from 101
7 July 202611 July 2026DirectSpirit AirlinesRT from 136
2 August 20269 August 2026DirectAmerican AirlinesRT from 183
11 September 202612 September 2026DirectAmerican AirlinesRT from 180
4 November 202611 November 2026DirectSpirit AirlinesRT from 138
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