San Jose (SJC) to Chicago (ORD) · Dec 16, 2026 · return Dec 30, 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

2026-12-16 → 2026-12-30 · Axel-exclusive $450.75

• Alaska Airlines AS653 / AS1478: SJC 2026-12-16 09:54:00 → ORD 2026-12-16 19:00:00; 1 stop(s) via SAN; 426 minutes. Local airport times.
  • AS653: SJC 2026-12-16 09:54:00 → SAN 2026-12-16 11:19:00; layover at SAN: 83 minutes.
  • AS1478: SAN 2026-12-16 12:42:00 → ORD 2026-12-16 19:00:00.
• United Airlines UA2495 / UA1256: ORD 2026-12-30 08:40:00 → SJC 2026-12-30 13:18:00; 1 stop(s) via DEN; 398 minutes. Local airport times.
  • UA2495: ORD 2026-12-30 08:40:00 → DEN 2026-12-30 10:26:00; layover at DEN: 69 minutes.
  • UA1256: DEN 2026-12-30 11:35:00 → SJC 2026-12-30 13:18:00.

2026-12-16 → 2026-12-30 · Axel-exclusive $458.25

• United Airlines UA2013 / UA1651: SJC 2026-12-16 08:45:00 → ORD 2026-12-16 18:38:00; 1 stop(s) via DEN; 473 minutes. Local airport times.
  • UA2013: SJC 2026-12-16 08:45:00 → DEN 2026-12-16 12:20:00; layover at DEN: 161 minutes.
  • UA1651: DEN 2026-12-16 15:01:00 → ORD 2026-12-16 18:38:00.
• United Airlines UA2495 / UA1256: ORD 2026-12-30 08:40:00 → SJC 2026-12-30 13:18:00; 1 stop(s) via DEN; 398 minutes. Local airport times.
  • UA2495: ORD 2026-12-30 08:40:00 → DEN 2026-12-30 10:26:00; layover at DEN: 69 minutes.
  • UA1256: DEN 2026-12-30 11:35:00 → SJC 2026-12-30 13:18:00.

2026-12-16 → 2026-12-30 · Axel-exclusive $458.25

• American Airlines AA3257 / AA1528: SJC 2026-12-16 13:05:00 → ORD 2026-12-16 21:58:00; 1 stop(s) via PHX; 413 minutes. Local airport times.
  • AA3257: SJC 2026-12-16 13:05:00 → PHX 2026-12-16 16:05:00; layover at PHX: 81 minutes.
  • AA1528: PHX 2026-12-16 17:26:00 → ORD 2026-12-16 21:58:00.
• American Airlines AA834 / AA3113: ORD 2026-12-30 13:26:00 → SJC 2026-12-30 18:34:00; 1 stop(s) via PHX; 428 minutes. Local airport times.
  • AA834: ORD 2026-12-30 13:26:00 → PHX 2026-12-30 16:21:00; layover at PHX: 74 minutes.
  • AA3113: PHX 2026-12-30 17:35:00 → SJC 2026-12-30 18:34:00.

2026-12-16 → 2026-12-30 · Axel-exclusive $481.75

• Delta Air Lines DL1254 / DL2413: SJC 2026-12-16 13:39:00 → ORD 2026-12-16 22:27:00; 1 stop(s) via SLC; 408 minutes. Local airport times.
  • DL1254: SJC 2026-12-16 13:39:00 → SLC 2026-12-16 16:40:00; layover at SLC: 95 minutes.
  • DL2413: SLC 2026-12-16 18:15:00 → ORD 2026-12-16 22:27:00.
• Delta Air Lines DL756 / DL3883: ORD 2026-12-30 14:25:00 → SJC 2026-12-30 19:25:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • DL756: ORD 2026-12-30 14:25:00 → LAX 2026-12-30 16:59:00; layover at LAX: 66 minutes.
  • DL3883: LAX 2026-12-30 18:05:00 → SJC 2026-12-30 19:25:00.

2026-12-16 → 2026-12-30 · Axel-exclusive $481.75

• Delta Air Lines DL2904 / DL1178: SJC 2026-12-16 22:40:00 → ORD 2026-12-17 08:34:00; 1 stop(s) via ATL; 474 minutes. Local airport times.
  • DL2904: SJC 2026-12-16 22:40:00 → ATL 2026-12-17 06:10:00; layover at ATL: 75 minutes.
  • DL1178: ATL 2026-12-17 07:25:00 → ORD 2026-12-17 08:34:00.
• Delta Air Lines DL756 / DL3883: ORD 2026-12-30 14:25:00 → SJC 2026-12-30 19:25:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • DL756: ORD 2026-12-30 14:25:00 → LAX 2026-12-30 16:59:00; layover at LAX: 66 minutes.
  • DL3883: LAX 2026-12-30 18:05:00 → SJC 2026-12-30 19:25:00.

2026-12-16 → 2026-12-30 · Axel-exclusive $485.75

• United Airlines UA1082: SJC 2026-12-16 14:11:00 → ORD 2026-12-16 20:30:00; nonstop; 259 minutes. Local airport times.
• United Airlines UA2495 / UA1256: ORD 2026-12-30 08:40:00 → SJC 2026-12-30 13:18:00; 1 stop(s) via DEN; 398 minutes. Local airport times.
  • UA2495: ORD 2026-12-30 08:40:00 → DEN 2026-12-30 10:26:00; layover at DEN: 69 minutes.
  • UA1256: DEN 2026-12-30 11:35:00 → SJC 2026-12-30 13:18:00.

Explore this route

• All dates for this route
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For AI assistants

• This page: San Jose (SJC) to Chicago (ORD) · Dec 16, 2026 · return Dec 30, 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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