Cheap Flights from JFK to MDW

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The Cheapest Round-trip Tickets from to

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2 May 20235 May 2023DirectRT from 229
27 May 202331 May 20231 StopRT from 270

The Cheapest Flights for this Month from to

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25 March 202328 March 20231 StopRT from 407
26 March 202326 March 20232 StopsRT from 1 074
27 March 20234 April 20231 StopRT from 282
28 March 202310 April 20231 StopRT from 324
30 March 20231 April 20231 StopRT from 336
31 March 20234 April 20231 StopRT from 297
1 April 20236 April 20231 StopRT from 578
3 April 202310 April 20231 StopRT from 324
5 April 202325 April 20231 StopRT from 311
8 April 202310 April 20231 StopRT from 455
15 April 202327 April 20231 StopRT from 419
21 April 202323 April 20231 StopRT from 329
24 April 202330 April 20232 StopsRT from 534
2 May 20235 May 20231 StopRT from 229
6 May 202320 May 20231 StopRT from 315
12 May 202312 May 20231 StopRT from 410
21 May 202321 May 20231 StopRT from 229
23 May 202323 May 20231 StopRT from 250
26 May 20234 June 20231 StopRT from 787
27 May 202331 May 20232 StopsRT from 270
31 May 20234 June 20231 StopRT from 490
1 June 202330 June 20231 StopRT from 441
2 June 20235 June 20231 StopRT from 557
2 June 20236 June 20232 StopsRT from 415
7 June 202310 June 20232 StopsRT from 323
8 June 202323 June 20231 StopRT from 377
9 June 202315 June 20231 StopRT from 315
11 June 202321 June 20231 StopRT from 260
14 June 202318 June 20232 StopsRT from 536
15 June 202319 June 20232 StopsRT from 835
16 June 20237 July 20231 StopRT from 259
17 June 202318 June 20232 StopsRT from 471
18 June 202320 June 20231 StopRT from 260
19 June 202325 June 20231 StopRT from 440
21 June 202324 June 20231 StopRT from 347
22 June 202328 June 20231 StopRT from 259
23 June 202324 June 20231 StopRT from 345
24 June 202327 June 20231 StopRT from 259
25 June 202325 July 20231 StopRT from 294
26 June 202323 July 20232 StopsRT from 486
28 June 20235 July 20231 StopRT from 278
29 June 20234 July 20231 StopRT from 422
30 June 20233 July 20231 StopRT from 331
1 July 20233 July 20231 StopRT from 284
1 July 20235 July 20232 StopsRT from 348
6 July 20238 July 20231 StopRT from 315
9 July 202311 July 20231 StopRT from 269
12 July 202318 July 20231 StopRT from 229
14 July 202326 July 20231 StopRT from 284
15 July 202319 July 20231 StopRT from 259
16 July 20233 August 20231 StopRT from 269
18 July 20232 August 20231 StopRT from 229
19 July 20232 August 20231 StopRT from 229
20 July 202315 August 20231 StopRT from 268
21 July 202310 August 20231 StopRT from 361
22 July 202325 July 20231 StopRT from 259
23 July 202329 July 20231 StopRT from 350
24 July 202326 July 20231 StopRT from 259
25 July 202321 August 20231 StopRT from 285
27 July 20238 August 20231 StopRT from 259
28 July 202331 July 20231 StopRT from 315
29 July 20231 August 20231 StopRT from 259
30 July 20233 August 20231 StopRT from 269
31 July 202319 August 20231 StopRT from 283
1 August 20239 August 20231 StopRT from 229
2 August 202310 August 20231 StopRT from 315
3 August 20237 August 20231 StopRT from 377
4 August 202310 August 20231 StopRT from 284
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 202312 August 20231 StopRT from 308
11 August 202314 August 20232 StopsRT from 580
12 August 20239 September 20231 StopRT from 284
13 August 202322 August 20231 StopRT from 364
17 August 202320 August 20231 StopRT from 425
19 August 202321 August 20231 StopRT from 384
20 August 20231 September 20231 StopRT from 347
31 August 20235 September 20231 StopRT from 370
1 September 20233 September 20231 StopRT from 363
4 September 20237 September 20231 StopRT from 264
5 September 20237 September 20231 StopRT from 229
17 September 202323 September 20231 StopRT from 331
19 September 202329 September 20231 StopRT from 380
5 October 20238 October 20231 StopRT from 421
6 October 202315 October 20231 StopRT from 527
6 October 202310 October 20232 StopsRT from 343
12 October 202314 October 20231 StopRT from 253
13 October 202316 October 20232 StopsRT from 323
12 November 202322 November 20231 StopRT from 319

The Cheapest Flights from to for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
27 March 20234 April 20231 StopRT from 282
5 April 202325 April 20231 StopRT from 311
2 May 20235 May 20231 StopRT from 229
16 June 20237 July 20231 StopRT from 259
18 July 20232 August 20231 StopRT from 229
1 August 20239 August 20231 StopRT from 229
5 September 20237 September 20231 StopRT from 229
12 October 202314 October 20231 StopRT from 253
12 November 202322 November 20231 StopRT from 319
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