Cheap Flights from SJC to CHI

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The Cheapest Round-trip Tickets from San Jose to Chicago

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1 November 20238 November 2023DirectSpirit AirlinesRT from 129

The Cheapest Flights for this Month from San Jose to Chicago

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4 October 202321 October 20231 StopUnited AirlinesRT from 672
5 October 202328 October 20231 StopAlaska AirlinesRT from 586
6 October 202311 October 20231 StopAmerican AirlinesRT from 502
7 October 202311 October 20231 StopUnited AirlinesRT from 800
8 October 202312 October 20231 StopAlaska AirlinesRT from 575
9 October 202310 October 20231 StopSpirit AirlinesRT from 307
10 October 202312 October 20231 StopSpirit AirlinesRT from 380
11 October 202325 October 20231 StopAlaska AirlinesRT from 499
12 October 202316 October 20231 StopUnited AirlinesRT from 635
13 October 202325 October 20231 StopUnited AirlinesRT from 554
14 October 202317 October 20231 StopSpirit AirlinesRT from 270
15 October 202320 October 20231 StopSpirit AirlinesRT from 365
16 October 202325 October 20231 StopAlaska AirlinesRT from 348
17 October 202324 October 20231 StopSpirit AirlinesRT from 164
18 October 202328 October 20231 StopDelta Air LinesRT from 319
19 October 202321 October 20231 StopDelta Air LinesRT from 346
20 October 202324 October 20231 StopDelta Air LinesRT from 340
21 October 202321 October 20231 StopAmerican AirlinesRT from 358
22 October 202328 October 20231 StopDelta Air LinesRT from 374
23 October 202330 October 20231 StopAlaska AirlinesRT from 242
24 October 202328 October 20231 StopSpirit AirlinesRT from 164
25 October 202328 October 20231 StopSpirit AirlinesRT from 164
26 October 20232 November 20231 StopDelta Air LinesRT from 296
27 October 202328 October 20231 StopDelta Air LinesRT from 296
28 October 202330 October 20231 StopAlaska AirlinesRT from 236
29 October 202331 October 20231 StopSpirit AirlinesRT from 221
30 October 20238 November 20231 StopSpirit AirlinesRT from 161
31 October 202331 October 20231 StopAlaska AirlinesRT from 237
1 November 20238 November 20231 StopSpirit AirlinesRT from 129
2 November 20234 November 20231 StopAlaska AirlinesRT from 295
3 November 20237 November 20231 StopAlaska AirlinesRT from 242
4 November 20239 November 20231 StopDelta Air LinesRT from 280
5 November 20237 November 20231 StopAlaska AirlinesRT from 295
6 November 202313 November 20231 StopSpirit AirlinesRT from 148
7 November 202329 November 20231 StopAlaska AirlinesRT from 242
8 November 202311 November 20231 StopSpirit AirlinesRT from 176
9 November 202311 November 20231 StopAlaska AirlinesRT from 282
10 November 202311 November 20231 StopDelta Air LinesRT from 280
11 November 202313 November 20231 StopSpirit AirlinesRT from 143
12 November 202314 November 20231 StopAlaska AirlinesRT from 295
13 November 202316 November 20231 StopSpirit AirlinesRT from 183
14 November 202329 November 20231 StopAlaska AirlinesRT from 236
15 November 202312 December 20231 StopAlaska AirlinesRT from 236
16 November 20234 December 20231 StopAlaska AirlinesRT from 308
17 November 202320 November 20231 StopSpirit AirlinesRT from 209
18 November 202330 November 20231 StopSpirit AirlinesRT from 240
19 November 202322 November 20231 StopSpirit AirlinesRT from 304
20 November 20232 December 20231 StopAlaska AirlinesRT from 346
21 November 20236 December 20231 StopUnited AirlinesRT from 378
22 November 202328 November 20231 StopSpirit AirlinesRT from 282
23 November 202329 November 20231 StopSpirit AirlinesRT from 202
24 November 20231 December 20231 StopDelta Air LinesRT from 377
25 November 20232 December 20231 StopUnited AirlinesRT from 558
26 November 202329 November 20231 StopDelta Air LinesRT from 720
27 November 20232 December 20231 StopDelta Air LinesRT from 336
28 November 20233 December 20231 StopSpirit AirlinesRT from 176
29 November 20232 December 20231 StopSpirit AirlinesRT from 166
30 November 202313 December 20231 StopAlaska AirlinesRT from 286
1 December 20239 December 20231 StopAlaska AirlinesRT from 269
2 December 20239 December 20231 StopSpirit AirlinesRT from 176
3 December 20239 December 20231 StopAlaska AirlinesRT from 269
4 December 202310 December 20231 StopAlaska AirlinesRT from 289
5 December 20239 December 20231 StopAlaska AirlinesRT from 236
6 December 20239 December 20231 StopAlaska AirlinesRT from 236
7 December 20239 December 20231 StopAlaska AirlinesRT from 269
8 December 202310 December 20231 StopSpirit AirlinesRT from 192
9 December 202312 December 20231 StopAlaska AirlinesRT from 236
10 December 202313 December 20231 StopDelta Air LinesRT from 307
11 December 202312 December 20231 StopDelta Air LinesRT from 307
12 December 202314 December 20231 StopAlaska AirlinesRT from 246
13 December 202310 January 20241 StopAlaska AirlinesRT from 246
14 December 20239 January 20241 StopAlaska AirlinesRT from 334
15 December 202320 December 20231 StopDelta Air LinesRT from 346
16 December 20233 January 20241 StopDelta Air LinesRT from 277
17 December 202320 December 20231 StopDelta Air LinesRT from 346
18 December 202311 January 20241 StopDelta Air LinesRT from 317
19 December 20233 January 20241 StopDelta Air LinesRT from 321
20 December 20233 January 20241 StopDelta Air LinesRT from 277
21 December 20236 January 20241 StopDelta Air LinesRT from 484
22 December 202323 December 20231 StopDelta Air LinesRT from 796
23 December 202320 January 20241 StopAlaska AirlinesRT from 452
24 December 20235 January 20241 StopAlaska AirlinesRT from 386
25 December 20233 January 20241 StopDelta Air LinesRT from 335
26 December 20232 January 20241 StopDelta Air LinesRT from 608
27 December 202313 January 20241 StopAlaska AirlinesRT from 452
28 December 20234 January 20241 StopDelta Air LinesRT from 439
29 December 20235 January 20241 StopAlaska AirlinesRT from 503
30 December 20234 January 20241 StopDelta Air LinesRT from 287
31 December 20233 January 20241 StopDelta Air LinesRT from 397
1 January 20246 January 20241 StopAlaska AirlinesRT from 454
2 January 20249 January 20241 StopDelta Air LinesRT from 383
3 January 20246 January 20241 StopAlaska AirlinesRT from 344
4 January 20249 January 20241 StopDelta Air LinesRT from 287
5 January 202410 January 20241 StopDelta Air LinesRT from 330
6 January 20249 January 20241 StopDelta Air LinesRT from 300
7 January 202410 January 20241 StopAlaska AirlinesRT from 308
8 January 20249 January 20241 StopDelta Air LinesRT from 307
9 January 202410 January 20241 StopDelta Air LinesRT from 264
10 January 202413 January 20241 StopDelta Air LinesRT from 289
11 January 202414 January 20241 StopAlaska AirlinesRT from 299
12 January 202416 January 20241 StopAlaska AirlinesRT from 298
13 January 202416 January 20241 StopDelta Air LinesRT from 269
14 January 202417 January 20241 StopDelta Air LinesRT from 330
15 January 202419 January 20241 StopAlaska AirlinesRT from 285
16 January 202423 January 20241 StopAlaska AirlinesRT from 297
17 January 202420 January 20241 StopDelta Air LinesRT from 269
18 January 202420 January 20241 StopAlaska AirlinesRT from 298
19 January 20246 February 20241 StopAlaska AirlinesRT from 298
20 January 202423 January 20241 StopDelta Air LinesRT from 269
21 January 202424 January 20241 StopDelta Air LinesRT from 307
22 January 202426 January 20241 StopAlaska AirlinesRT from 302
23 January 202424 January 20241 StopDelta Air LinesRT from 264
24 January 202427 January 20241 StopAlaska AirlinesRT from 272
25 January 20243 February 20241 StopAlaska AirlinesRT from 298
26 January 202431 January 20241 StopDelta Air LinesRT from 307
27 January 202430 January 20241 StopDelta Air LinesRT from 269
28 January 202431 January 20241 StopDelta Air LinesRT from 307
29 January 202430 January 20241 StopDelta Air LinesRT from 307
30 January 202431 January 20241 StopDelta Air LinesRT from 264
31 January 20243 February 20241 StopDelta Air LinesRT from 289
1 February 20246 February 20241 StopAlaska AirlinesRT from 279
5 February 202417 February 20241 StopAlaska AirlinesRT from 308
6 February 202410 February 20241 StopDelta Air LinesRT from 289
8 February 202411 February 20241 StopAlaska AirlinesRT from 305
9 February 20249 February 20241 StopUnited AirlinesRT from 408
12 February 202416 February 20241 StopAlaska AirlinesRT from 339
13 February 202420 February 20241 StopAlaska AirlinesRT from 252
15 February 202419 February 20241 StopAlaska AirlinesRT from 352
16 February 202418 February 20241 StopAlaska AirlinesRT from 365
17 February 202424 February 20241 StopAlaska AirlinesRT from 308
18 February 202424 February 20241 StopAlaska AirlinesRT from 284
21 February 202425 February 20241 StopAlaska AirlinesRT from 305
22 February 202425 February 20241 StopAlaska AirlinesRT from 367
24 February 202423 March 20242 StopsAlaska AirlinesRT from 740
28 February 20245 March 20242 StopsAlaska AirlinesRT from 636
1 March 20244 March 20241 StopAlaska AirlinesRT from 321
3 March 20243 March 20242 StopsAlaska AirlinesRT from 952
4 March 20248 March 20241 StopAlaska AirlinesRT from 445
5 March 20246 March 20241 StopDelta Air LinesRT from 290
6 March 20249 March 20242 StopsAlaska AirlinesRT from 682
7 March 202411 March 20241 StopAlaska AirlinesRT from 361
10 March 202413 March 20241 StopAlaska AirlinesRT from 357
11 March 202415 March 20241 StopUnited AirlinesRT from 479
12 March 202418 March 20241 StopAlaska AirlinesRT from 378
13 March 202419 March 20241 StopDelta Air LinesRT from 364
14 March 202419 March 20241 StopAlaska AirlinesRT from 373
16 March 202419 March 20241 StopAlaska AirlinesRT from 365
17 March 202431 March 2024DirectUnited AirlinesRT from 478
18 March 202426 March 20241 StopAlaska AirlinesRT from 360
19 March 202425 March 20241 StopDelta Air LinesRT from 469
20 March 202423 March 20241 StopAlaska AirlinesRT from 349
21 March 202424 March 20241 StopUnited AirlinesRT from 503
22 March 202424 March 20241 StopAlaska AirlinesRT from 374
23 March 202425 March 20241 StopAlaska AirlinesRT from 374
25 March 202425 March 20241 StopUnited AirlinesRT from 471
26 March 20244 April 20242 StopsAlaska AirlinesRT from 622
27 March 20248 April 20242 StopsAlaska AirlinesRT from 408
28 March 20241 April 20241 StopAlaska AirlinesRT from 404
29 March 202431 March 20241 StopUnited AirlinesRT from 580
30 March 20243 April 20241 StopAlaska AirlinesRT from 417
31 March 20244 April 2024DirectUnited AirlinesRT from 575
3 April 20247 April 20241 StopUnited AirlinesRT from 419
4 April 20248 April 20241 StopUnited AirlinesRT from 419
5 April 20248 April 20241 StopUnited AirlinesRT from 419
8 April 202413 April 20241 StopAlaska AirlinesRT from 357
10 April 202416 April 20241 StopAlaska AirlinesRT from 365
11 April 202415 April 20241 StopUnited AirlinesRT from 419
12 April 202422 April 20241 StopUnited AirlinesRT from 419
13 April 202415 April 20241 StopAlaska AirlinesRT from 307
17 April 202420 April 20241 StopAlaska AirlinesRT from 400
18 April 202421 April 20241 StopUnited AirlinesRT from 593
19 April 202419 April 2024DirectUnited AirlinesRT from 446
22 April 20247 May 20242 StopsJetBlue AirwaysRT from 579
23 April 202427 April 20241 StopAlaska AirlinesRT from 350
29 April 202418 May 20241 StopAlaska AirlinesRT from 330
5 May 202412 May 20241 StopAlaska AirlinesRT from 416
7 May 202410 May 20241 StopJetBlue AirwaysRT from 518
8 May 202412 May 20241 StopDelta Air LinesRT from 439
9 May 202411 May 20241 StopDelta Air LinesRT from 428
12 May 202418 May 20241 StopJetBlue AirwaysRT from 624
16 May 202422 May 2024DirectUnited AirlinesRT from 461
17 May 202421 May 20241 StopDelta Air LinesRT from 488
19 May 202421 May 20241 StopAlaska AirlinesRT from 354
22 May 202427 May 2024DirectUnited AirlinesRT from 501
23 May 202426 May 20241 StopAlaska AirlinesRT from 365
24 May 202426 May 20241 StopUnited AirlinesRT from 451
31 May 20242 June 20241 StopUnited AirlinesRT from 511
3 June 202422 June 20241 StopUnited AirlinesRT from 479
5 June 202411 June 20241 StopAlaska AirlinesRT from 380
8 June 202422 June 20241 StopUnited AirlinesRT from 500
9 June 20243 July 2024DirectUnited AirlinesRT from 515
13 June 202425 June 20241 StopAlaska AirlinesRT from 339
14 June 202421 June 20241 StopAlaska AirlinesRT from 339
17 June 202410 July 2024DirectUnited AirlinesRT from 527
19 June 202417 July 20241 StopAlaska AirlinesRT from 354
23 June 202427 June 20241 StopAlaska AirlinesRT from 428
26 June 20243 July 20241 StopAlaska AirlinesRT from 339
27 June 20241 July 20241 StopAlaska AirlinesRT from 398
28 June 202430 June 20241 StopAlaska AirlinesRT from 398
29 June 20245 July 20241 StopAlaska AirlinesRT from 374
30 June 20246 July 20241 StopAlaska AirlinesRT from 374
2 July 20246 July 20241 StopAlaska AirlinesRT from 380
3 July 20247 July 20241 StopUnited AirlinesRT from 570
4 July 202413 July 20241 StopAlaska AirlinesRT from 424
6 July 202417 July 20241 StopAlaska AirlinesRT from 378
8 July 202412 July 20241 StopAlaska AirlinesRT from 374
9 July 202420 July 20241 StopAlaska AirlinesRT from 399
11 July 202416 July 20241 StopAlaska AirlinesRT from 354
18 July 202421 July 20241 StopUnited AirlinesRT from 500
19 July 202422 July 20241 StopUnited AirlinesRT from 558
24 July 20243 August 2024DirectUnited AirlinesRT from 533
7 August 202411 August 20241 StopUnited AirlinesRT from 468
8 August 202411 August 20241 StopUnited AirlinesRT from 468
14 August 202418 August 20241 StopAlaska AirlinesRT from 360
15 August 202417 August 20241 StopAlaska AirlinesRT from 339
22 August 202424 August 20241 StopAlaska AirlinesRT from 365

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

Departure atReturn atStopsAirlineFind tickets
9 October 202310 October 20231 StopSpirit AirlinesRT from 307
1 November 20238 November 20231 StopSpirit AirlinesRT from 129
2 December 20239 December 20231 StopSpirit AirlinesRT from 176
9 January 202410 January 20241 StopDelta Air LinesRT from 264
13 February 202420 February 20241 StopAlaska AirlinesRT from 252
5 March 20246 March 20241 StopDelta Air LinesRT from 290
13 April 202415 April 20241 StopAlaska AirlinesRT from 307
19 May 202421 May 20241 StopAlaska AirlinesRT from 354
26 June 20243 July 20241 StopAlaska AirlinesRT from 339
11 July 202416 July 20241 StopAlaska AirlinesRT from 354
15 August 202417 August 20241 StopAlaska AirlinesRT from 339
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