Cheap Flights from NYC to CHI

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The Cheapest Round-trip Tickets from New York to Chicago

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6 December 20259 December 2025DirectFrontier AirlinesRT from 69

The Cheapest Flights for this Month from New York to Chicago

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29 October 20251 November 2025DirectSpirit AirlinesRT from 157
3 November 20259 November 2025DirectSpirit AirlinesRT from 134
20 November 202522 November 2025DirectSpirit AirlinesRT from 89
21 November 202523 November 2025DirectFrontier AirlinesRT from 98
28 November 202528 November 2025DirectSpirit AirlinesRT from 84
29 November 20251 December 20251 StopSpirit AirlinesRT from 254
5 December 20256 December 2025DirectFrontier AirlinesRT from 76
6 December 20259 December 2025DirectFrontier AirlinesRT from 69
8 December 20259 December 2025DirectSpirit AirlinesRT from 80
11 January 202613 January 2026DirectSpirit AirlinesRT from 76
14 January 202616 January 2026DirectFrontier AirlinesRT from 97
1 March 20264 March 2026DirectSpirit AirlinesRT from 120
8 March 202622 March 2026DirectFrontier AirlinesRT from 275
23 April 202628 April 2026DirectJetBlue AirwaysRT from 201
1 June 20264 June 2026DirectAmerican AirlinesRT from 204

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

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29 October 20251 November 2025DirectSpirit AirlinesRT from 157
28 November 202528 November 2025DirectSpirit AirlinesRT from 84
6 December 20259 December 2025DirectFrontier AirlinesRT from 69
11 January 202613 January 2026DirectSpirit AirlinesRT from 76
1 March 20264 March 2026DirectSpirit AirlinesRT from 120
23 April 202628 April 2026DirectJetBlue AirwaysRT from 201
1 June 20264 June 2026DirectAmerican AirlinesRT from 204
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