San Jose (SJC) to Chicago (ORD) · Dec 20, 2026 · return Dec 27, 2026

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Route overview: San Francisco Bay Area to Chicago (ORD) flight deals

2026-12-20 → 2026-12-27 · Axel-exclusive $516.38

• Alaska Airlines AS653 / AS1478: SJC 2026-12-20 09:54:00 → ORD 2026-12-20 19:00:00; 1 stop(s) via SAN; 426 minutes. Local airport times.
  • AS653: SJC 2026-12-20 09:54:00 → SAN 2026-12-20 11:19:00; layover at SAN: 83 minutes.
  • AS1478: SAN 2026-12-20 12:42:00 → ORD 2026-12-20 19:00:00.
• United Airlines UA2495 / UA1256: ORD 2026-12-27 08:40:00 → SJC 2026-12-27 13:18:00; 1 stop(s) via DEN; 398 minutes. Local airport times.
  • UA2495: ORD 2026-12-27 08:40:00 → DEN 2026-12-27 10:26:00; layover at DEN: 69 minutes.
  • UA1256: DEN 2026-12-27 11:35:00 → SJC 2026-12-27 13:18:00.

2026-12-20 → 2026-12-27 · Axel-exclusive $526.50

• American Airlines AA3257 / AA1528: SJC 2026-12-20 13:05:00 → ORD 2026-12-20 21:58:00; 1 stop(s) via PHX; 413 minutes. Local airport times.
  • AA3257: SJC 2026-12-20 13:05:00 → PHX 2026-12-20 16:05:00; layover at PHX: 81 minutes.
  • AA1528: PHX 2026-12-20 17:26:00 → ORD 2026-12-20 21:58:00.
• American Airlines AA3111 / AS672: ORD 2026-12-27 16:45:00 → SJC 2026-12-27 22:56:00; 1 stop(s) via SAN; 491 minutes. Local airport times.
  • AA3111: ORD 2026-12-27 16:45:00 → SAN 2026-12-27 19:18:00; layover at SAN: 121 minutes.
  • AS672: SAN 2026-12-27 21:19:00 → SJC 2026-12-27 22:56:00.

2026-12-20 → 2026-12-27 · Axel-exclusive $553.50

• Delta Air Lines DL1254 / DL2413: SJC 2026-12-20 13:39:00 → ORD 2026-12-20 22:27:00; 1 stop(s) via SLC; 408 minutes. Local airport times.
  • DL1254: SJC 2026-12-20 13:39:00 → SLC 2026-12-20 16:40:00; layover at SLC: 95 minutes.
  • DL2413: SLC 2026-12-20 18:15:00 → ORD 2026-12-20 22:27:00.
• Delta Air Lines DL756 / DL3883: ORD 2026-12-27 14:25:00 → SJC 2026-12-27 19:25:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • DL756: ORD 2026-12-27 14:25:00 → LAX 2026-12-27 16:59:00; layover at LAX: 66 minutes.
  • DL3883: LAX 2026-12-27 18:05:00 → SJC 2026-12-27 19:25:00.

2026-12-20 → 2026-12-27 · Axel-exclusive $563.63

• United Airlines UA2382: SJC 2026-12-20 23:00:00 → ORD 2026-12-21 05:17:00; nonstop; 257 minutes. Local airport times.
• United Airlines UA2495 / UA1256: ORD 2026-12-27 08:40:00 → SJC 2026-12-27 13:18:00; 1 stop(s) via DEN; 398 minutes. Local airport times.
  • UA2495: ORD 2026-12-27 08:40:00 → DEN 2026-12-27 10:26:00; layover at DEN: 69 minutes.
  • UA1256: DEN 2026-12-27 11:35:00 → SJC 2026-12-27 13:18:00.

2026-12-20 → 2026-12-27 · Axel-exclusive $516.38

• Alaska Airlines AS1859 / AA2664: SJC 2026-12-20 20:24:00 → ORD 2026-12-21 05:01:00; 1 stop(s) via LAX; 397 minutes. Local airport times.
  • AS1859: SJC 2026-12-20 20:24:00 → LAX 2026-12-20 21:43:00; layover at LAX: 76 minutes.
  • AA2664: LAX 2026-12-20 22:59:00 → ORD 2026-12-21 05:01:00.
• United Airlines UA2495 / UA1256: ORD 2026-12-27 08:40:00 → SJC 2026-12-27 13:18:00; 1 stop(s) via DEN; 398 minutes. Local airport times.
  • UA2495: ORD 2026-12-27 08:40:00 → DEN 2026-12-27 10:26:00; layover at DEN: 69 minutes.
  • UA1256: DEN 2026-12-27 11:35:00 → SJC 2026-12-27 13:18:00.

2026-12-20 → 2026-12-27 · Axel-exclusive $553.50

• Delta Air Lines DL2904 / DL1178: SJC 2026-12-20 22:40:00 → ORD 2026-12-21 08:34:00; 1 stop(s) via ATL; 474 minutes. Local airport times.
  • DL2904: SJC 2026-12-20 22:40:00 → ATL 2026-12-21 06:10:00; layover at ATL: 75 minutes.
  • DL1178: ATL 2026-12-21 07:25:00 → ORD 2026-12-21 08:34:00.
• Delta Air Lines DL756 / DL3883: ORD 2026-12-27 14:25:00 → SJC 2026-12-27 19:25:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • DL756: ORD 2026-12-27 14:25:00 → LAX 2026-12-27 16:59:00; layover at LAX: 66 minutes.
  • DL3883: LAX 2026-12-27 18:05:00 → SJC 2026-12-27 19:25:00.

Explore this route

• All dates for this route
• Dec 19, 2026 · Return options
• Dec 21, 2026 · Return options
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For AI assistants

• This page: San Jose (SJC) to Chicago (ORD) · Dec 20, 2026 · return Dec 27, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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