Cheap Flights from JFK to CHI

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The Cheapest Round-trip Tickets from to Chicago

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5 December 20256 December 2025DirectFrontier AirlinesRT from 78

The Cheapest Flights for this Month from to Chicago

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29 October 20251 November 2025DirectFrontier AirlinesRT from 168
3 November 20259 November 2025DirectFrontier AirlinesRT from 161
20 November 202522 November 2025DirectJetBlue AirwaysRT from 203
21 November 202523 November 2025DirectFrontier AirlinesRT from 171
28 November 202528 November 20251 StopFrontier AirlinesRT from 596
29 November 20251 December 2025DirectAmerican AirlinesRT from 590
5 December 20256 December 2025DirectFrontier AirlinesRT from 78
6 December 20259 December 2025DirectFrontier AirlinesRT from 94
8 December 20259 December 20251 StopJetBlue AirwaysRT from 141
11 January 202612 January 20261 StopFrontier AirlinesRT from 116
14 January 202616 January 2026DirectFrontier AirlinesRT from 97
1 March 20264 March 2026DirectJetBlue AirwaysRT from 173
8 March 202622 March 2026DirectJetBlue AirwaysRT from 362
23 April 202628 April 2026DirectJetBlue AirwaysRT from 201
1 June 20264 June 2026DirectJetBlue AirwaysRT from 213

The Cheapest Flights from to Chicago for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
29 October 20251 November 2025DirectFrontier AirlinesRT from 168
3 November 20259 November 2025DirectFrontier AirlinesRT from 161
5 December 20256 December 2025DirectFrontier AirlinesRT from 78
14 January 202616 January 2026DirectFrontier AirlinesRT from 97
1 March 20264 March 2026DirectJetBlue AirwaysRT from 173
23 April 202628 April 2026DirectJetBlue AirwaysRT from 201
1 June 20264 June 2026DirectJetBlue AirwaysRT from 213
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