Cheap Flights from NYC to MDW

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The Cheapest Round-trip Tickets from New York to

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5 January 20248 January 2024DirectSouthwest AirlinesRT from 98

The Cheapest Flights for this Month from New York to

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28 November 20233 December 2023DirectSouthwest AirlinesRT from 218
29 November 20236 December 2023DirectSouthwest AirlinesRT from 184
30 November 20235 December 2023DirectSouthwest AirlinesRT from 221
1 December 20234 December 2023DirectSouthwest AirlinesRT from 212
2 December 20239 December 20231 StopFrontier AirlinesRT from 142
3 December 202310 December 20231 StopSouthwest AirlinesRT from 239
4 December 20235 December 2023DirectSouthwest AirlinesRT from 209
5 December 202312 December 20231 StopFrontier AirlinesRT from 159
6 December 202318 December 20231 StopDelta Air LinesRT from 207
7 December 20239 December 20231 StopFrontier AirlinesRT from 184
8 December 202311 December 2023DirectSouthwest AirlinesRT from 176
9 December 202318 December 20231 StopDelta Air LinesRT from 160
10 December 202315 December 20231 StopFrontier AirlinesRT from 216
11 December 202314 December 2023DirectSouthwest AirlinesRT from 198
12 December 202312 December 20231 StopFrontier AirlinesRT from 181
13 December 202314 December 20231 StopDelta Air LinesRT from 160
14 December 202318 December 20231 StopFrontier AirlinesRT from 113
15 December 202318 December 2023DirectSouthwest AirlinesRT from 162
16 December 202317 December 20231 StopSouthwest AirlinesRT from 227
17 December 202318 December 20231 StopDelta Air LinesRT from 122
18 December 202325 December 20232 StopsSpirit AirlinesRT from 281
19 December 202327 December 20231 StopFrontier AirlinesRT from 314
20 December 202322 December 20231 StopFrontier AirlinesRT from 529
21 December 202315 January 20241 StopFrontier AirlinesRT from 411
22 December 202325 December 2023DirectSouthwest AirlinesRT from 551
23 December 202330 December 20231 StopSouthwest AirlinesRT from 580
24 December 202315 January 2024DirectSouthwest AirlinesRT from 170
25 December 202315 January 2024DirectSouthwest AirlinesRT from 170
26 December 20232 January 2024DirectSouthwest AirlinesRT from 289
27 December 20232 January 2024DirectSouthwest AirlinesRT from 301
28 December 20231 January 2024DirectSouthwest AirlinesRT from 329
29 December 20235 January 20241 StopSouthwest AirlinesRT from 172
30 December 20232 January 20241 StopSouthwest AirlinesRT from 341
31 December 20237 January 2024DirectSouthwest AirlinesRT from 154
1 January 20244 January 20241 StopDelta Air LinesRT from 137
2 January 20242 January 20241 StopSouthwest AirlinesRT from 307
3 January 20245 January 20241 StopDelta Air LinesRT from 122
4 January 20249 January 2024DirectSouthwest AirlinesRT from 102
5 January 20248 January 2024DirectSouthwest AirlinesRT from 98
6 January 202413 January 20241 StopDelta Air LinesRT from 152
7 January 202413 January 20241 StopDelta Air LinesRT from 167
8 January 202422 January 20241 StopDelta Air LinesRT from 132
9 January 202411 January 2024DirectSouthwest AirlinesRT from 134
10 January 202412 January 20241 StopFrontier AirlinesRT from 108
11 January 202417 January 20241 StopDelta Air LinesRT from 142
12 January 202415 January 2024DirectSouthwest AirlinesRT from 192
13 January 202414 January 20241 StopDelta Air LinesRT from 142
14 January 202418 January 20241 StopDelta Air LinesRT from 132
15 January 202429 January 20241 StopDelta Air LinesRT from 132
16 January 202416 January 20241 StopDelta Air LinesRT from 132
17 January 202421 January 20241 StopDelta Air LinesRT from 132
18 January 202420 January 2024DirectSouthwest AirlinesRT from 117
19 January 202428 January 20241 StopDelta Air LinesRT from 147
20 January 202420 January 2024DirectSouthwest AirlinesRT from 134
21 January 202423 January 2024DirectSouthwest AirlinesRT from 135
22 January 202428 January 20241 StopDelta Air LinesRT from 132
23 January 202423 January 20241 StopDelta Air LinesRT from 132
24 January 202428 January 20241 StopDelta Air LinesRT from 132
25 January 202429 January 20241 StopDelta Air LinesRT from 142
26 January 202430 January 2024DirectSouthwest AirlinesRT from 141
27 January 20243 February 20241 StopFrontier AirlinesRT from 127
28 January 202430 January 20241 StopDelta Air LinesRT from 132
29 January 202431 January 20241 StopDelta Air LinesRT from 147
30 January 20244 February 20241 StopFrontier AirlinesRT from 127
31 January 202413 February 20241 StopDelta Air LinesRT from 152
1 February 20245 February 2024DirectSouthwest AirlinesRT from 125
2 February 20244 February 2024DirectSouthwest AirlinesRT from 142
3 February 20246 February 20241 StopFrontier AirlinesRT from 127
4 February 20244 February 20241 StopDelta Air LinesRT from 132
5 February 20247 February 2024DirectSouthwest AirlinesRT from 123
6 February 202411 February 20241 StopDelta Air LinesRT from 167
7 February 202412 February 20241 StopDelta Air LinesRT from 156
8 February 202410 February 20241 StopDelta Air LinesRT from 132
9 February 202412 February 20241 StopDelta Air LinesRT from 132
10 February 202411 February 20241 StopFrontier AirlinesRT from 127
11 February 202413 February 20241 StopDelta Air LinesRT from 304
12 February 202414 February 2024DirectSouthwest AirlinesRT from 113
13 February 202420 February 20241 StopDelta Air LinesRT from 132
14 February 202422 February 20241 StopDelta Air LinesRT from 132
15 February 202419 February 2024DirectSouthwest AirlinesRT from 228
16 February 202423 February 20241 StopDelta Air LinesRT from 162
17 February 202421 February 20241 StopDelta Air LinesRT from 170
18 February 202422 February 20241 StopDelta Air LinesRT from 132
19 February 202423 February 20241 StopDelta Air LinesRT from 182
20 February 202426 February 20241 StopFrontier AirlinesRT from 124
21 February 202425 February 20241 StopDelta Air LinesRT from 132
22 February 202426 February 20241 StopFrontier AirlinesRT from 127
23 February 20241 March 20241 StopFrontier AirlinesRT from 131
24 February 202428 February 20241 StopDelta Air LinesRT from 132
25 February 202427 February 20241 StopDelta Air LinesRT from 157
26 February 20246 March 20241 StopDelta Air LinesRT from 132
27 February 202427 February 20241 StopDelta Air LinesRT from 162
28 February 20245 March 20241 StopDelta Air LinesRT from 132
29 February 20243 March 20241 StopFrontier AirlinesRT from 127
1 March 20241 March 20241 StopFrontier AirlinesRT from 127
2 March 20245 March 20241 StopFrontier AirlinesRT from 127
3 March 20245 March 20241 StopDelta Air LinesRT from 287
4 March 20244 March 20241 StopFrontier AirlinesRT from 127
5 March 20246 March 20241 StopDelta Air LinesRT from 292
6 March 202411 March 20241 StopFrontier AirlinesRT from 197
7 March 202411 March 2024DirectSouthwest AirlinesRT from 217
8 March 202410 March 20241 StopDelta Air LinesRT from 304
9 March 202416 March 20241 StopDelta Air LinesRT from 309
10 March 202417 March 20241 StopDelta Air LinesRT from 309
11 March 202414 March 20241 StopFrontier AirlinesRT from 267
12 March 202419 March 20241 StopDelta Air LinesRT from 142
13 March 202418 March 20241 StopFrontier AirlinesRT from 267
14 March 202417 March 20241 StopSouthwest AirlinesRT from 244
15 March 202417 March 20241 StopDelta Air LinesRT from 304
16 March 202418 March 20241 StopDelta Air LinesRT from 317
17 March 202418 March 20241 StopDelta Air LinesRT from 456
18 March 202425 March 20241 StopFrontier AirlinesRT from 267
19 March 202425 March 20241 StopDelta Air LinesRT from 231
20 March 202424 March 20241 StopFrontier AirlinesRT from 426
21 March 202426 March 20241 StopDelta Air LinesRT from 187
22 March 202424 March 20241 StopDelta Air LinesRT from 348
23 March 202427 March 20241 StopDelta Air LinesRT from 287
24 March 202427 March 20241 StopDelta Air LinesRT from 235
25 March 202427 March 20241 StopDelta Air LinesRT from 210
26 March 20242 April 20241 StopDelta Air LinesRT from 172
27 March 202431 March 20241 StopDelta Air LinesRT from 242
28 March 20245 April 2024DirectSouthwest AirlinesRT from 312
30 March 20246 April 20241 StopSouthwest AirlinesRT from 442
31 March 20244 April 20241 StopDelta Air LinesRT from 397
3 April 20247 April 20241 StopDelta Air LinesRT from 331
4 April 20247 April 20241 StopDelta Air LinesRT from 396
5 April 202412 April 20241 StopDelta Air LinesRT from 751
7 April 202412 April 20241 StopDelta Air LinesRT from 676
8 April 202413 April 20242 StopsUnited AirlinesRT from 770
9 April 202417 April 20241 StopDelta Air LinesRT from 175
10 April 202410 April 20241 StopDelta Air LinesRT from 257
11 April 202415 April 20241 StopDelta Air LinesRT from 352
12 April 202415 April 20241 StopDelta Air LinesRT from 358
14 April 202422 April 20241 StopDelta Air LinesRT from 440
15 April 202421 April 20241 StopDelta Air LinesRT from 357
16 April 202426 April 20241 StopDelta Air LinesRT from 195
17 April 202417 April 20241 StopDelta Air LinesRT from 230
18 April 202421 April 20241 StopDelta Air LinesRT from 345
19 April 202422 April 20241 StopDelta Air LinesRT from 425
20 April 202425 April 20241 StopDelta Air LinesRT from 325
21 April 202424 April 20241 StopDelta Air LinesRT from 312
24 April 202427 April 20241 StopDelta Air LinesRT from 218
25 April 202410 May 20241 StopDelta Air LinesRT from 230
26 April 202427 April 20241 StopDelta Air LinesRT from 312
28 April 202430 April 20241 StopDelta Air LinesRT from 287
29 April 20245 May 20241 StopDelta Air LinesRT from 345
30 April 20248 May 20241 StopDelta Air LinesRT from 172
1 May 20248 May 20241 StopDelta Air LinesRT from 172
2 May 20244 May 20241 StopDelta Air LinesRT from 230
3 May 20246 May 20241 StopDelta Air LinesRT from 253
6 May 20246 May 20241 StopDelta Air LinesRT from 297
7 May 202415 May 20241 StopDelta Air LinesRT from 172
8 May 202412 May 20241 StopDelta Air LinesRT from 195
9 May 202414 May 20241 StopDelta Air LinesRT from 230
10 May 202412 May 20241 StopDelta Air LinesRT from 495
11 May 202419 May 20241 StopDelta Air LinesRT from 257
15 May 202415 May 20241 StopDelta Air LinesRT from 230
16 May 202429 May 20241 StopDelta Air LinesRT from 230
19 May 202424 May 20241 StopDelta Air LinesRT from 436
20 May 20244 June 2024DirectSouthwest AirlinesRT from 273
21 May 202417 June 2024DirectSouthwest AirlinesRT from 251
22 May 202429 May 20241 StopDelta Air LinesRT from 212
23 May 202426 May 20241 StopDelta Air LinesRT from 270
24 May 20248 June 20241 StopDelta Air LinesRT from 353
25 May 20241 June 20242 StopsDelta Air LinesRT from 619
26 May 202429 May 20241 StopDelta Air LinesRT from 209
27 May 202429 May 20241 StopDelta Air LinesRT from 250
28 May 20243 June 20241 StopDelta Air LinesRT from 289
29 May 20242 June 20241 StopDelta Air LinesRT from 195
30 May 20242 June 20241 StopDelta Air LinesRT from 293
31 May 20241 June 20241 StopDelta Air LinesRT from 318
1 June 20242 June 20241 StopDelta Air LinesRT from 660
2 June 20249 June 20241 StopDelta Air LinesRT from 527
4 June 20245 June 20241 StopDelta Air LinesRT from 255
5 June 20249 June 20241 StopDelta Air LinesRT from 278
6 June 20249 June 20241 StopDelta Air LinesRT from 318
7 June 202428 June 20241 StopDelta Air LinesRT from 309
9 June 202415 June 20241 StopDelta Air LinesRT from 490
12 June 202417 June 20241 StopDelta Air LinesRT from 337
13 June 202427 June 20241 StopDelta Air LinesRT from 355
14 June 202416 June 20241 StopDelta Air LinesRT from 350
18 June 202423 June 20241 StopDelta Air LinesRT from 412
19 June 202410 July 20241 StopDelta Air LinesRT from 257
20 June 202426 June 20241 StopDelta Air LinesRT from 270
21 June 202426 June 20241 StopDelta Air LinesRT from 309
23 June 202423 June 20241 StopDelta Air LinesRT from 607
25 June 202423 July 20241 StopDelta Air LinesRT from 271
27 June 20241 July 20241 StopDelta Air LinesRT from 290
28 June 202430 June 20242 StopsDelta Air LinesRT from 1 040
30 June 202410 July 20242 StopsUnited AirlinesRT from 721
3 July 20247 July 20242 StopsDelta Air LinesRT from 875
4 July 20247 July 20241 StopDelta Air LinesRT from 269
7 July 20249 July 20241 StopDelta Air LinesRT from 512
10 July 202415 July 20241 StopDelta Air LinesRT from 269
11 July 202416 July 20241 StopDelta Air LinesRT from 403
12 July 202414 July 20241 StopDelta Air LinesRT from 597
18 July 202412 August 20241 StopDelta Air LinesRT from 380
19 July 202415 August 20241 StopDelta Air LinesRT from 336
20 July 202414 August 20241 StopDelta Air LinesRT from 392
21 July 202415 August 20241 StopDelta Air LinesRT from 446
23 July 202415 August 20241 StopDelta Air LinesRT from 234
24 July 202428 July 20241 StopDelta Air LinesRT from 517
28 July 202428 July 20241 StopDelta Air LinesRT from 562
31 July 20243 August 20241 StopDelta Air LinesRT from 310
1 August 202415 August 20241 StopDelta Air LinesRT from 476
2 August 20249 August 20241 StopDelta Air LinesRT from 309
6 August 202415 August 20241 StopDelta Air LinesRT from 261
7 August 20247 August 20241 StopDelta Air LinesRT from 257
14 August 202419 August 20241 StopDelta Air LinesRT from 280
15 August 20244 September 20241 StopDelta Air LinesRT from 372
16 August 202419 August 20242 StopsDelta Air LinesRT from 723
26 August 202426 August 20241 StopDelta Air LinesRT from 305
27 August 20245 September 20241 StopDelta Air LinesRT from 197
30 August 20242 September 20242 StopsUnited AirlinesRT from 811
1 September 20241 September 20241 StopDelta Air LinesRT from 292
2 September 202416 September 20242 StopsDelta Air LinesRT from 948
5 September 20249 September 20241 StopDelta Air LinesRT from 211
6 September 20248 September 20241 StopDelta Air LinesRT from 372
8 September 202412 September 20241 StopDelta Air LinesRT from 450
10 September 202418 September 20241 StopDelta Air LinesRT from 175
12 September 202423 September 20241 StopDelta Air LinesRT from 310
13 September 202420 September 20241 StopDelta Air LinesRT from 480
15 September 202419 September 20242 StopsDelta Air LinesRT from 776
20 September 202422 September 20241 StopDelta Air LinesRT from 517
25 September 202419 October 20241 StopDelta Air LinesRT from 189
26 September 20243 October 20241 StopDelta Air LinesRT from 230
27 September 202430 September 20241 StopDelta Air LinesRT from 362
2 October 20249 October 20241 StopDelta Air LinesRT from 172
10 October 202416 October 20241 StopDelta Air LinesRT from 230
11 October 202415 October 20241 StopDelta Air LinesRT from 432
12 October 202414 October 20241 StopDelta Air LinesRT from 260
14 October 202418 October 20241 StopDelta Air LinesRT from 362
17 October 202421 October 20241 StopDelta Air LinesRT from 253

The Cheapest Flights from New York to for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
29 November 20236 December 2023DirectSouthwest AirlinesRT from 184
14 December 202318 December 20231 StopFrontier AirlinesRT from 113
5 January 20248 January 2024DirectSouthwest AirlinesRT from 98
12 February 202414 February 2024DirectSouthwest AirlinesRT from 113
7 March 202411 March 2024DirectSouthwest AirlinesRT from 217
30 April 20248 May 20241 StopDelta Air LinesRT from 172
21 May 202417 June 2024DirectSouthwest AirlinesRT from 251
4 June 20245 June 20241 StopDelta Air LinesRT from 255
23 July 202415 August 20241 StopDelta Air LinesRT from 234
27 August 20245 September 20241 StopDelta Air LinesRT from 197
10 September 202418 September 20241 StopDelta Air LinesRT from 175
2 October 20249 October 20241 StopDelta Air LinesRT from 172
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