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 July 202618 July 2026DirectUnited AirlinesRT from 145

The Cheapest Flights for this Month from New York to Chicago

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2 July 20264 July 20261 StopAmerican AirlinesRT from 372
3 July 20266 July 20261 StopAmerican AirlinesRT from 385
4 July 20266 July 20261 StopFrontier AirlinesRT from 317
5 July 20269 July 20261 StopSouthwest AirlinesRT from 378
7 July 20269 July 20261 StopFrontier AirlinesRT from 319
8 July 202610 July 20261 StopFrontier AirlinesRT from 276
9 July 202610 July 20261 StopFrontier AirlinesRT from 283
10 July 202612 July 20261 StopAmerican AirlinesRT from 275
13 July 202617 July 20261 StopFrontier AirlinesRT from 277
14 July 202616 July 2026DirectjetBlueRT from 219
16 July 202618 July 2026DirectSouthwest AirlinesRT from 209
18 July 202618 July 20261 StopUnited AirlinesRT from 145
19 July 202621 July 2026DirectSouthwest AirlinesRT from 199
20 July 202622 July 2026DirectSouthwest AirlinesRT from 218
22 July 202629 July 2026DirectSouthwest AirlinesRT from 154
25 July 202629 July 2026DirectSouthwest AirlinesRT from 188
28 July 20261 August 2026DirectSouthwest AirlinesRT from 183
29 July 20263 August 20261 StopUnited AirlinesRT from 257
31 July 20263 August 20261 StopFrontier AirlinesRT from 271
5 August 20267 August 2026DirectjetBlueRT from 187
11 August 202613 August 2026DirectSouthwest AirlinesRT from 179
12 August 202616 August 2026DirectjetBlueRT from 192
13 August 202613 August 2026DirectjetBlueRT from 195
15 August 202616 August 2026DirectSouthwest AirlinesRT from 185
17 August 202620 August 2026DirectjetBlueRT from 192
19 August 202620 August 2026DirectjetBlueRT from 172
27 August 202630 August 2026DirectSouthwest AirlinesRT from 203
1 September 202610 September 2026DirectjetBlueRT from 176
4 September 20265 September 2026DirectjetBlueRT from 177
7 September 202620 October 2026DirectjetBlueRT from 199
10 September 202614 September 2026DirectSouthwest AirlinesRT from 184
27 September 20267 October 2026DirectSouthwest AirlinesRT from 153
4 October 20266 October 2026DirectSouthwest AirlinesRT from 183
4 November 202611 November 2026DirectjetBlueRT from 205

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

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18 July 202618 July 20261 StopUnited AirlinesRT from 145
19 August 202620 August 2026DirectjetBlueRT from 172
27 September 20267 October 2026DirectSouthwest AirlinesRT from 153
4 October 20266 October 2026DirectSouthwest AirlinesRT from 183
4 November 202611 November 2026DirectjetBlueRT from 205
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