Cheap Flights from NYC to MDW

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The Cheapest Round-trip Tickets from New York to

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4 April 20235 April 2023DirectRT from 148
18 April 20239 May 20231 StopRT from 163
27 May 202331 May 20231 StopRT from 270

The Cheapest Flights for this Month from New York to

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25 March 20232 April 20231 StopRT from 401
26 March 202327 March 2023DirectRT from 426
27 March 20235 April 2023DirectRT from 276
28 March 202320 April 2023DirectRT from 285
29 March 20235 April 20231 StopRT from 247
30 March 20236 April 2023DirectRT from 248
31 March 20237 April 2023DirectRT from 276
1 April 20233 April 20231 StopRT from 322
2 April 202317 April 2023DirectRT from 398
3 April 20236 April 20231 StopRT from 324
4 April 20235 April 2023DirectRT from 148
5 April 202310 April 2023DirectRT from 196
6 April 202310 April 2023DirectRT from 225
7 April 202321 April 20231 StopRT from 207
8 April 202310 April 2023DirectRT from 287
9 April 202311 April 2023DirectRT from 259
10 April 202310 April 20231 StopRT from 250
11 April 202321 April 2023DirectRT from 177
12 April 202319 April 20231 StopRT from 172
13 April 202314 April 2023DirectRT from 220
14 April 202317 April 2023DirectRT from 186
15 April 202317 April 2023DirectRT from 168
16 April 202321 April 2023DirectRT from 223
17 April 202317 April 20231 StopRT from 270
18 April 20239 May 20231 StopRT from 163
19 April 202323 April 2023DirectRT from 186
20 April 202330 April 2023DirectRT from 166
21 April 202323 April 2023DirectRT from 186
22 April 202324 April 2023DirectRT from 196
23 April 202325 April 20231 StopRT from 199
24 April 20232 May 20231 StopRT from 166
25 April 202325 April 20231 StopRT from 175
26 April 20232 May 20231 StopRT from 184
27 April 202311 May 2023DirectRT from 162
28 April 202330 April 2023DirectRT from 196
29 April 20231 May 2023DirectRT from 197
30 April 202323 May 20231 StopRT from 166
1 May 20234 May 20231 StopRT from 182
2 May 20235 May 2023DirectRT from 186
3 May 20237 May 2023DirectRT from 186
4 May 20238 May 2023DirectRT from 166
5 May 20238 May 2023DirectRT from 186
6 May 20238 May 2023DirectRT from 195
7 May 202323 May 20231 StopRT from 199
8 May 202320 May 2023DirectRT from 221
9 May 202313 May 20231 StopRT from 199
10 May 202315 May 2023DirectRT from 161
11 May 202315 May 20231 StopRT from 356
12 May 202315 May 20231 StopRT from 183
13 May 202331 May 20231 StopRT from 166
14 May 202326 May 20231 StopRT from 259
16 May 202319 May 20231 StopRT from 295
17 May 202318 May 20231 StopRT from 497
19 May 202321 May 20231 StopRT from 208
20 May 202322 May 20231 StopRT from 192
21 May 202321 May 2023DirectRT from 403
22 May 202325 May 2023DirectRT from 249
23 May 202326 May 20231 StopRT from 208
24 May 202327 May 20231 StopRT from 205
25 May 202329 May 2023DirectRT from 220
26 May 202328 May 20231 StopRT from 201
27 May 202331 May 20232 StopsRT from 270
28 May 20233 June 20231 StopRT from 259
31 May 202314 June 20231 StopRT from 199
1 June 20237 June 20231 StopRT from 195
2 June 20236 June 20231 StopRT from 406
3 June 20233 July 20232 StopsRT from 345
4 June 20236 June 20231 StopRT from 233
5 June 20239 June 20231 StopRT from 232
6 June 202310 June 2023DirectRT from 214
7 June 202313 June 20231 StopRT from 199
8 June 202327 June 20231 StopRT from 175
9 June 202311 June 2023DirectRT from 263
10 June 202320 June 20231 StopRT from 217
11 June 202313 June 20231 StopRT from 223
12 June 202326 June 20231 StopRT from 208
13 June 202314 June 20231 StopRT from 199
14 June 202328 June 20231 StopRT from 212
15 June 202320 June 20231 StopRT from 226
16 June 202315 July 20231 StopRT from 199
17 June 202311 July 20231 StopRT from 199
18 June 20237 July 20231 StopRT from 223
20 June 202329 June 20231 StopRT from 223
21 June 202325 June 20231 StopRT from 623
22 June 202326 June 20231 StopRT from 488
23 June 20233 July 20232 StopsRT from 294
24 June 202328 June 20231 StopRT from 291
25 June 202329 June 20232 StopsRT from 428
26 June 202323 July 20232 StopsRT from 486
27 June 202328 June 20232 StopsRT from 319
28 June 20235 July 20231 StopRT from 278
29 June 20235 July 20231 StopRT from 285
30 June 20233 July 20232 StopsRT from 347
1 July 20235 July 20232 StopsRT from 348
2 July 20238 July 20231 StopRT from 199
3 July 202315 July 20231 StopRT from 199
4 July 202311 July 20231 StopRT from 175
5 July 202324 July 20231 StopRT from 357
6 July 202310 July 20231 StopRT from 231
7 July 202311 July 20232 StopsRT from 373
8 July 202312 July 20231 StopRT from 205
9 July 202312 July 20231 StopRT from 295
10 July 202314 July 20231 StopRT from 292
11 July 202316 July 20231 StopRT from 471
12 July 202318 July 20231 StopRT from 229
13 July 202316 July 20231 StopRT from 805
14 July 202317 July 20232 StopsRT from 355
15 July 202325 July 20231 StopRT from 259
16 July 20233 August 20231 StopRT from 269
18 July 202323 July 20231 StopRT from 502
19 July 20232 August 20231 StopRT from 229
21 July 202325 July 20232 StopsRT from 317
22 July 202325 July 20231 StopRT from 259
23 July 202326 July 20231 StopRT from 294
24 July 202326 July 20231 StopRT from 259
25 July 202321 August 20231 StopRT from 285
26 July 202331 July 20231 StopRT from 392
27 July 202316 August 20231 StopRT from 376
28 July 20239 August 20231 StopRT from 284
29 July 202331 July 20231 StopRT from 291
30 July 20231 August 20231 StopRT from 269
31 July 202319 August 20231 StopRT from 283
1 August 20239 August 20231 StopRT from 229
2 August 20237 August 2023DirectRT from 213
3 August 20237 August 20231 StopRT from 619
4 August 202323 August 20231 StopRT from 361
5 August 20238 August 20231 StopRT from 259
6 August 20239 August 20231 StopRT from 332
7 August 202326 August 20231 StopRT from 315
8 August 20238 August 20231 StopRT from 175
9 August 202322 August 20231 StopRT from 451
10 August 202313 August 20231 StopRT from 488
11 August 202331 August 20231 StopRT from 376
12 August 202315 August 20231 StopRT from 226
13 August 202324 August 20231 StopRT from 293
14 August 202311 September 20231 StopRT from 254
17 August 202321 August 20231 StopRT from 317
18 August 202328 August 20232 StopsRT from 760
19 August 202321 August 20231 StopRT from 384
20 August 20231 September 20231 StopRT from 347
21 August 202330 August 20231 StopRT from 481
22 August 202326 August 20231 StopRT from 402
23 August 20232 September 20231 StopRT from 292
24 August 202331 August 20231 StopRT from 629
25 August 202327 August 20231 StopRT from 487
26 August 20232 September 20231 StopRT from 376
29 August 20234 September 20231 StopRT from 259
30 August 20236 September 20231 StopRT from 261
31 August 20233 September 20231 StopRT from 347
1 September 20233 September 20231 StopRT from 557
2 September 202310 September 20231 StopRT from 412
3 September 202315 September 20231 StopRT from 229
4 September 20237 September 20231 StopRT from 264
5 September 20237 September 20231 StopRT from 229
7 September 202310 September 20232 StopsRT from 595
8 September 202311 September 20231 StopRT from 585
15 September 202317 September 20231 StopRT from 472
16 September 202321 September 20231 StopRT from 620
17 September 202313 October 20231 StopRT from 285
19 September 20235 October 20231 StopRT from 199
20 September 202324 September 20231 StopRT from 430
23 September 202324 September 20231 StopRT from 412
24 September 20233 October 20231 StopRT from 371
25 September 202329 September 20231 StopRT from 259
26 September 20233 October 20231 StopRT from 585
2 October 202318 October 20231 StopRT from 1 045
3 October 20238 October 20231 StopRT from 291
5 October 202310 October 20231 StopRT from 226
6 October 20239 October 20231 StopRT from 514
7 October 20239 October 20231 StopRT from 317
8 October 202321 October 20232 StopsRT from 815
9 October 202311 October 20231 StopRT from 346
13 October 202316 October 20232 StopsRT from 323
14 October 202314 October 20231 StopRT from 232
15 October 202317 October 20231 StopRT from 261
16 October 202318 October 20231 StopRT from 261
19 October 20231 November 20231 StopRT from 346
20 October 20239 November 20231 StopRT from 521
22 October 20234 November 20231 StopRT from 346
23 October 202325 October 20231 StopRT from 346
24 October 202329 October 20231 StopRT from 325
27 October 202327 October 20231 StopRT from 286
28 October 20235 November 20232 StopsRT from 321
3 November 20233 November 20231 StopRT from 321
6 November 20238 November 20231 StopRT from 270
8 November 202312 November 20231 StopRT from 259
12 November 202322 November 20231 StopRT from 319
13 November 202318 November 20231 StopRT from 279
23 November 202328 November 20231 StopRT from 261
25 November 20233 December 20231 StopRT from 565
16 December 20237 January 20241 StopRT from 315
22 December 20234 January 20241 StopRT from 321
26 December 20232 January 20241 StopRT from 476
5 January 20249 January 20241 StopRT from 312
24 January 202431 January 20241 StopRT from 184
1 February 20244 February 20242 StopsRT from 448

The Cheapest Flights from New York to for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
30 March 20236 April 2023DirectRT from 248
4 April 20235 April 2023DirectRT from 148
10 May 202315 May 2023DirectRT from 161
14 June 202328 June 20231 StopRT from 212
29 July 202331 July 20231 StopRT from 291
2 August 20237 August 2023DirectRT from 213
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