Cheap Flights by Route

Cheap Flights from CHI to SJU

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The Cheapest Round-trip Tickets from Chicago to San Juan

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6 August 202214 August 2022DirectRT from 271
24 August 202227 August 20221 StopRT from 255
13 June 202220 June 20221 StopRT from 510

The Cheapest Flights for this Month from Chicago to San Juan

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22 May 20225 June 2022DirectRT from 536
23 May 202231 May 2022DirectRT from 380
24 May 20224 June 20221 StopRT from 377
25 May 20221 June 20222 StopsRT from 507
26 May 202229 May 20221 StopRT from 408
27 May 202229 May 20221 StopRT from 398
28 May 202229 May 20221 StopRT from 401
29 May 20221 June 20221 StopRT from 425
30 May 202218 June 20222 StopsRT from 476
31 May 20225 June 2022DirectRT from 396
1 June 20225 June 20221 StopRT from 409
2 June 20225 June 20221 StopRT from 429
3 June 20225 June 20221 StopRT from 376
4 June 202211 June 2022DirectRT from 350
5 June 202218 June 2022DirectRT from 365
6 June 202213 June 20221 StopRT from 455
7 June 202227 June 2022DirectRT from 254
8 June 202222 June 20221 StopRT from 421
9 June 202216 June 20221 StopRT from 527
10 June 202212 June 20221 StopRT from 352
11 June 202218 June 2022DirectRT from 329
12 June 202216 June 2022DirectRT from 433
13 June 202220 June 20222 StopsRT from 510
14 June 202217 June 20221 StopRT from 510
15 June 20226 July 20221 StopRT from 486
16 June 202220 June 20221 StopRT from 517
17 June 202221 June 20221 StopRT from 424
18 June 202221 June 20221 StopRT from 414
19 June 20226 July 20222 StopsRT from 404
20 June 202211 July 20221 StopRT from 493
21 June 202212 July 20221 StopRT from 442
22 June 202225 June 20221 StopRT from 445
23 June 202227 June 20221 StopRT from 476
24 June 202227 June 20221 StopRT from 387
25 June 20221 July 2022DirectRT from 467
26 June 202227 June 20221 StopRT from 448
27 June 20224 July 20221 StopRT from 383
28 June 20224 July 20221 StopRT from 383
29 June 20224 July 20221 StopRT from 514
30 June 20224 July 20221 StopRT from 526
1 July 20225 July 20221 StopRT from 481
2 July 20229 July 2022DirectRT from 303
3 July 202219 July 20221 StopRT from 397
4 July 202219 July 20221 StopRT from 392
5 July 202212 July 20221 StopRT from 408
6 July 202221 July 20221 StopRT from 495
7 July 202213 July 20221 StopRT from 444
8 July 202212 July 20221 StopRT from 406
9 July 202213 July 20221 StopRT from 404
10 July 202222 July 20221 StopRT from 242
11 July 202229 July 20221 StopRT from 232
12 July 20221 August 20221 StopRT from 518
13 July 202220 July 20221 StopRT from 437
14 July 202217 July 20221 StopRT from 443
15 July 202220 July 20221 StopRT from 438
16 July 202223 July 2022DirectRT from 328
17 July 202225 July 20221 StopRT from 243
18 July 202223 July 20221 StopRT from 386
19 July 202219 July 20221 StopRT from 227
20 July 202229 July 20221 StopRT from 491
21 July 202224 July 20221 StopRT from 401
22 July 202231 July 20221 StopRT from 460
23 July 202227 July 20221 StopRT from 399
24 July 202226 July 20221 StopRT from 222
25 July 202230 July 20221 StopRT from 437
26 July 202230 July 20221 StopRT from 419
27 July 20221 August 20221 StopRT from 456
28 July 202214 August 20222 StopsRT from 440
29 July 20224 August 20222 StopsRT from 376
30 July 20221 August 2022DirectRT from 244
31 July 202214 August 20221 StopRT from 418
1 August 20224 August 20221 StopRT from 232
2 August 20225 August 20221 StopRT from 218
3 August 202220 August 20221 StopRT from 243
4 August 202210 August 20221 StopRT from 382
5 August 20229 August 20221 StopRT from 394
6 August 202214 August 2022DirectRT from 271
7 August 202221 August 20221 StopRT from 450
8 August 202211 August 20222 StopsRT from 400
9 August 202216 August 20221 StopRT from 360
10 August 202218 August 20221 StopRT from 233
11 August 202215 August 20221 StopRT from 359
12 August 202216 August 20221 StopRT from 342
13 August 202227 August 2022DirectRT from 313
14 August 20221 September 20222 StopsRT from 397
15 August 202223 August 20221 StopRT from 232
16 August 202219 August 20221 StopRT from 232
17 August 202223 August 20221 StopRT from 232
18 August 202222 August 20221 StopRT from 296
19 August 202222 August 20221 StopRT from 290
20 August 202228 August 2022DirectRT from 244
21 August 202229 August 20221 StopRT from 420
22 August 20225 September 20221 StopRT from 400
23 August 202230 August 20221 StopRT from 232
24 August 202227 August 20221 StopRT from 255
25 August 202228 August 20221 StopRT from 317
26 August 202231 August 20221 StopRT from 228
27 August 202231 August 20221 StopRT from 228
28 August 202210 September 20221 StopRT from 300
29 August 202212 September 20221 StopRT from 319
30 August 202213 September 20221 StopRT from 319
31 August 20224 September 20221 StopRT from 333
1 September 20225 September 20221 StopRT from 414
2 September 202216 September 20221 StopRT from 399
3 September 202224 September 20221 StopRT from 325
4 September 20224 September 20221 StopRT from 237
5 September 202219 September 20221 StopRT from 418
6 September 20226 September 20221 StopRT from 227
7 September 202214 September 20221 StopRT from 232
8 September 202216 September 20221 StopRT from 312
9 September 202214 September 20221 StopRT from 286
10 September 202224 September 20221 StopRT from 278
11 September 202225 September 20221 StopRT from 371
12 September 202226 September 20221 StopRT from 371
13 September 202227 September 20221 StopRT from 319
14 September 202224 September 20221 StopRT from 316
15 September 202217 September 20221 StopRT from 300
16 September 202219 September 20221 StopRT from 350
17 September 20221 October 20221 StopRT from 296
18 September 202225 September 20221 StopRT from 348
19 September 202225 September 20221 StopRT from 348
20 September 202224 September 20221 StopRT from 278
21 September 202228 September 20221 StopRT from 298
22 September 202226 September 20221 StopRT from 344
23 September 202225 September 20221 StopRT from 249
24 September 202228 September 20221 StopRT from 319
25 September 202229 September 20221 StopRT from 401
26 September 20223 October 20221 StopRT from 326
27 September 202230 September 20221 StopRT from 318
28 September 20225 October 20221 StopRT from 218
29 September 20225 October 20221 StopRT from 334
30 September 20223 October 20221 StopRT from 299
1 October 20229 October 2022DirectRT from 244
2 October 20227 October 20221 StopRT from 232
3 October 202228 October 20222 StopsRT from 400
4 October 20228 October 20221 StopRT from 317
5 October 202210 October 20221 StopRT from 339
6 October 202211 October 20221 StopRT from 228
7 October 20222 November 20221 StopRT from 344
8 October 202211 October 20221 StopRT from 318
9 October 20222 November 20221 StopRT from 398
10 October 202213 October 20221 StopRT from 423
11 October 202219 October 20221 StopRT from 304
12 October 202218 October 20221 StopRT from 218
13 October 202218 October 20221 StopRT from 330
14 October 20229 November 20221 StopRT from 401
15 October 202219 October 20221 StopRT from 341
16 October 202219 October 20221 StopRT from 232
17 October 202222 October 20221 StopRT from 382
18 October 202225 October 20221 StopRT from 285
19 October 202222 October 20221 StopRT from 341
20 October 202225 October 20221 StopRT from 243
21 October 20222 November 20221 StopRT from 385
22 October 202228 October 20221 StopRT from 325
23 October 202216 November 20221 StopRT from 379
24 October 202227 October 20221 StopRT from 395
25 October 20228 November 20221 StopRT from 285
26 October 20221 November 20221 StopRT from 329
27 October 20225 November 20221 StopRT from 334
28 October 20225 November 20221 StopRT from 334
29 October 20228 November 20221 StopRT from 306
30 October 20223 November 2022DirectRT from 392
31 October 20222 November 20221 StopRT from 233
1 November 20229 November 20221 StopRT from 218
2 November 202230 November 20221 StopRT from 323
3 November 20226 November 2022DirectRT from 229
4 November 202211 November 20221 StopRT from 233
5 November 202212 November 2022DirectRT from 244
6 November 202213 November 20221 StopRT from 422
7 November 202212 November 20221 StopRT from 341
8 November 202214 November 20221 StopRT from 243
9 November 20227 December 20221 StopRT from 327
10 November 202215 November 20221 StopRT from 368
11 November 202216 November 20221 StopRT from 379
12 November 20227 December 20221 StopRT from 327
13 November 20227 December 20221 StopRT from 347
14 November 20227 December 20221 StopRT from 351
15 November 202223 November 2022DirectRT from 343
16 November 202223 November 20221 StopRT from 285
17 November 202221 November 20221 StopRT from 358
18 November 202228 November 20221 StopRT from 285
19 November 20223 December 20222 StopsRT from 397
20 November 202224 November 2022DirectRT from 446
21 November 202224 November 20221 StopRT from 412
22 November 20226 December 20221 StopRT from 364
23 November 202228 November 2022DirectRT from 381
24 November 202221 December 20221 StopRT from 390
25 November 20222 December 2022DirectRT from 402
26 November 20223 December 20221 StopRT from 428
27 November 202229 November 20221 StopRT from 285
28 November 20222 December 20221 StopRT from 472
29 November 20225 December 20221 StopRT from 405
30 November 202212 December 20221 StopRT from 673
1 December 20226 December 20221 StopRT from 300
2 December 20229 December 20221 StopRT from 504
3 December 202211 December 2022DirectRT from 259
4 December 202210 December 2022DirectRT from 276
5 December 20229 December 20221 StopRT from 427
6 December 202214 December 20221 StopRT from 285
7 December 202214 December 20221 StopRT from 285
8 December 202215 December 20221 StopRT from 344
9 December 202212 December 20221 StopRT from 504
10 December 202215 December 20222 StopsRT from 353
11 December 202215 December 20221 StopRT from 366
12 December 202217 December 20221 StopRT from 763
13 December 202214 December 20221 StopRT from 371
14 December 202218 December 20221 StopRT from 292
15 December 202220 December 20221 StopRT from 494
16 December 202217 December 20221 StopRT from 653
17 December 20224 January 20231 StopRT from 437
18 December 202222 December 20221 StopRT from 285
19 December 20221 January 20231 StopRT from 285
20 December 202221 December 20221 StopRT from 280
21 December 202227 December 20222 StopsRT from 474
22 December 202214 January 20231 StopRT from 691
23 December 20226 January 20231 StopRT from 752
24 December 20223 January 20231 StopRT from 285
25 December 202230 December 20222 StopsRT from 697
26 December 20222 January 2023DirectRT from 619
27 December 202231 December 20221 StopRT from 268
28 December 202211 January 20231 StopRT from 673
29 December 20226 January 20231 StopRT from 544
30 December 20226 January 20231 StopRT from 556
31 December 202214 January 20231 StopRT from 390
1 January 202331 January 20231 StopRT from 385
2 January 202325 January 20231 StopRT from 589
3 January 202310 January 20231 StopRT from 417
4 January 20231 February 20231 StopRT from 411
5 January 202310 January 20231 StopRT from 285
6 January 202311 January 20231 StopRT from 285
7 January 202314 January 20231 StopRT from 348
8 January 20231 February 20231 StopRT from 412
9 January 202323 January 20231 StopRT from 282
10 January 202323 January 20231 StopRT from 282
11 January 20238 February 20231 StopRT from 326
12 January 202317 January 20231 StopRT from 385
13 January 202318 January 20231 StopRT from 346
14 January 202321 January 20232 StopsRT from 375
15 January 202322 January 20231 StopRT from 300
16 January 20238 February 20231 StopRT from 385
17 January 202324 January 20231 StopRT from 296
18 January 202315 February 20231 StopRT from 316
19 January 202326 January 20231 StopRT from 282
20 January 202324 January 20231 StopRT from 300
21 January 202328 January 20231 StopRT from 308
22 January 20231 February 20231 StopRT from 336
23 January 202315 February 20231 StopRT from 322
24 January 202331 January 20231 StopRT from 285
25 January 202329 January 20231 StopRT from 431
26 January 202329 January 20231 StopRT from 412
27 January 20234 February 2023DirectRT from 363
28 January 202331 January 20231 StopRT from 286
29 January 20235 February 20231 StopRT from 301
31 January 20235 February 2023DirectRT from 407
1 February 20239 February 20231 StopRT from 296
2 February 20237 February 20231 StopRT from 302
3 February 202317 February 2023DirectRT from 276
4 February 202311 February 20231 StopRT from 322
5 February 202311 February 2023DirectRT from 282
6 February 202311 February 20231 StopRT from 282
7 February 20237 February 20231 StopRT from 292
8 February 202315 February 20231 StopRT from 315
9 February 202313 February 20231 StopRT from 344
10 February 202317 February 20231 StopRT from 347
11 February 202325 February 2023DirectRT from 259
12 February 202322 February 20231 StopRT from 285
13 February 202317 February 2023DirectRT from 330
14 February 202318 February 20231 StopRT from 339
15 February 202322 February 20231 StopRT from 285
16 February 202321 February 20231 StopRT from 411
17 February 202325 February 20231 StopRT from 423
18 February 202325 February 20231 StopRT from 426
19 February 202325 February 2023DirectRT from 276
20 February 202325 February 20231 StopRT from 418
21 February 202315 March 2023DirectRT from 452
22 February 20231 March 2023DirectRT from 375
23 February 202326 February 20231 StopRT from 411
24 February 202327 February 20231 StopRT from 366
25 February 20234 March 2023DirectRT from 430
26 February 20234 March 2023DirectRT from 696
27 February 20235 March 2023DirectRT from 417
1 March 202315 March 20231 StopRT from 397
2 March 20236 March 20231 StopRT from 292
3 March 202311 March 20231 StopRT from 376
4 March 202311 March 2023DirectRT from 276
5 March 202311 March 2023DirectRT from 902
6 March 202312 March 2023DirectRT from 445
7 March 202311 March 2023DirectRT from 422
8 March 202314 March 20231 StopRT from 390
10 March 202313 March 20231 StopRT from 410
11 March 202316 March 20231 StopRT from 274
12 March 202318 March 20231 StopRT from 454
13 March 202317 March 20231 StopRT from 483
14 March 20235 April 20231 StopRT from 408
15 March 202324 March 20231 StopRT from 373
16 March 202322 March 20231 StopRT from 399
17 March 202328 March 20231 StopRT from 286
18 March 202312 April 2023DirectRT from 770
19 March 202323 March 2023DirectRT from 711
20 March 202327 March 20231 StopRT from 415
21 March 202312 April 20231 StopRT from 363
22 March 202330 March 20231 StopRT from 513
23 March 202330 March 20231 StopRT from 431
24 March 20233 April 20231 StopRT from 285
25 March 202330 March 20231 StopRT from 405
26 March 202331 March 2023DirectRT from 276
27 March 20231 April 20232 StopsRT from 412
28 March 202319 April 20231 StopRT from 1 599
29 March 20239 April 20231 StopRT from 524
30 March 20238 April 20231 StopRT from 408
31 March 20237 April 20231 StopRT from 378
1 April 20239 April 2023DirectRT from 276
3 April 20238 April 20231 StopRT from 400
4 April 20239 April 20231 StopRT from 533
6 April 202316 April 2023DirectRT from 477
7 April 202310 April 20232 StopsRT from 400
8 April 202316 April 20231 StopRT from 639
9 April 202316 April 2023DirectRT from 940
10 April 202316 April 2023DirectRT from 721
11 April 202318 April 2023DirectRT from 508
12 April 202319 April 2023DirectRT from 529
13 April 202319 April 2023DirectRT from 774
15 April 202322 April 20231 StopRT from 2 317

The Cheapest Flights from Chicago to San Juan for the Year Ahead

Departure atReturn atStopsAirlineFind tickets
24 May 20224 June 20221 StopRT from 377
11 June 202218 June 2022DirectRT from 329
2 July 20229 July 2022DirectRT from 303
24 August 202227 August 20221 StopRT from 255
30 September 20223 October 20221 StopRT from 299
13 October 202218 October 20221 StopRT from 330
15 November 202223 November 2022DirectRT from 343
26 December 20222 January 2023DirectRT from 619
31 March 20237 April 20231 StopRT from 378
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