Cheap Flights from NYC to CHI

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The Cheapest Round-trip Tickets from New York to Chicago

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10 March 202612 March 2026DirectFrontier AirlinesRT from 48

The Cheapest Flights for this Month from New York to Chicago

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15 February 202628 February 2026DirectFrontier AirlinesRT from 216
16 February 202616 February 2026DirectFrontier AirlinesRT from 252
17 February 202619 February 20261 StopSpirit AirlinesRT from 261
18 February 202620 February 2026DirectSpirit AirlinesRT from 207
19 February 202620 February 2026DirectSpirit AirlinesRT from 188
20 February 202623 February 2026DirectFrontier AirlinesRT from 84
21 February 202622 February 2026DirectSpirit AirlinesRT from 137
22 February 202624 February 2026DirectSpirit AirlinesRT from 75
26 February 202628 February 2026DirectSpirit AirlinesRT from 78
27 February 20261 March 2026DirectSpirit AirlinesRT from 92
10 March 202612 March 2026DirectFrontier AirlinesRT from 48
12 March 202614 March 20261 StopSpirit AirlinesRT from 121
13 March 202615 March 20261 StopFrontier AirlinesRT from 208
17 March 202619 March 2026DirectSpirit AirlinesRT from 82
27 March 202627 March 2026DirectSpirit AirlinesRT from 138
1 April 20269 April 2026DirectSpirit AirlinesRT from 114
3 April 20266 April 2026DirectUnited AirlinesRT from 107
8 April 202612 April 2026DirectSpirit AirlinesRT from 125
17 April 202619 May 2026DirectFrontier AirlinesRT from 68
20 April 20264 May 2026DirectFrontier AirlinesRT from 56
23 April 202628 April 2026DirectFrontier AirlinesRT from 72
4 May 202618 May 2026DirectSpirit AirlinesRT from 117
6 May 20268 May 2026DirectFrontier AirlinesRT from 98
7 May 20268 May 2026DirectFrontier AirlinesRT from 98
8 May 202610 May 2026DirectFrontier AirlinesRT from 73
12 May 202615 May 2026DirectFrontier AirlinesRT from 55
13 May 202615 May 2026DirectFrontier AirlinesRT from 57
26 May 202628 May 2026DirectAmerican AirlinesRT from 150
2 June 20269 June 2026DirectSpirit AirlinesRT from 115
4 June 20268 June 2026DirectSouthwest AirlinesRT from 145
5 June 20265 June 2026DirectAmerican AirlinesRT from 206
23 June 202630 June 2026DirectFrontier AirlinesRT from 173
25 June 202628 June 2026DirectJetBlue AirwaysRT from 197
30 June 202630 June 2026DirectSpirit AirlinesRT from 198
10 July 202611 July 2026DirectSpirit AirlinesRT from 162
24 July 202626 July 2026DirectSpirit AirlinesRT from 158
25 August 20269 September 2026DirectSpirit AirlinesRT from 144
11 September 202612 September 2026DirectAmerican AirlinesRT from 197
6 November 202610 November 2026DirectAmerican AirlinesRT from 206
21 December 202624 December 2026DirectAmerican AirlinesRT from 251
31 December 20267 January 2027DirectAmerican AirlinesRT from 206
5 January 202712 January 2027DirectUnited AirlinesRT from 256
10 January 202717 January 20273 StopsUnited AirlinesRT from 523
11 January 202718 January 20272 StopsUnited AirlinesRT from 557
12 January 202719 January 20273 StopsAir CanadaRT from 755
14 January 202721 January 20273 StopsAir CanadaRT from 773
16 January 202718 January 20272 StopsAir CanadaRT from 819

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

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22 February 202624 February 2026DirectSpirit AirlinesRT from 75
10 March 202612 March 2026DirectFrontier AirlinesRT from 48
20 April 20264 May 2026DirectFrontier AirlinesRT from 56
12 May 202615 May 2026DirectFrontier AirlinesRT from 55
2 June 20269 June 2026DirectSpirit AirlinesRT from 115
24 July 202626 July 2026DirectSpirit AirlinesRT from 158
25 August 20269 September 2026DirectSpirit AirlinesRT from 144
11 September 202612 September 2026DirectAmerican AirlinesRT from 197
6 November 202610 November 2026DirectAmerican AirlinesRT from 206
31 December 20267 January 2027DirectAmerican AirlinesRT from 206
5 January 202712 January 2027DirectUnited AirlinesRT from 256
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