San Jose (SJC) to Chicago (ORD) · Dec 22, 2026 · return Dec 24, 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.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Chicago for these nights (Dec 22–24, 2026 · 2 nights · 2 adults, 1 room): 3★ The Willows Hotel, $205 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $241 total · 5★ Nobu Hotel Chicago, $630 total

All hotels in Chicago

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

2026-12-22 → 2026-12-24 · Axel-exclusive $600.76

• United Airlines UA2004: SJC 2026-12-22 14:14:00 → ORD 2026-12-22 20:32:00; nonstop; 258 minutes. Local airport times.
• United Airlines UA1840: ORD 2026-12-24 19:45:00 → SJC 2026-12-24 22:45:00; nonstop; 300 minutes. Local airport times.

2026-12-22 → 2026-12-24 · Axel-exclusive $526.50

• American Airlines AA3257 / AA1528: SJC 2026-12-22 13:05:00 → ORD 2026-12-22 21:58:00; 1 stop(s) via PHX; 413 minutes. Local airport times.
  • AA3257: SJC 2026-12-22 13:05:00 → PHX 2026-12-22 16:05:00; layover at PHX: 81 minutes.
  • AA1528: PHX 2026-12-22 17:26:00 → ORD 2026-12-22 21:58:00.
• American Airlines AA834 / AA3113: ORD 2026-12-24 13:26:00 → SJC 2026-12-24 18:34:00; 1 stop(s) via PHX; 428 minutes. Local airport times.
  • AA834: ORD 2026-12-24 13:26:00 → PHX 2026-12-24 16:21:00; layover at PHX: 74 minutes.
  • AA3113: PHX 2026-12-24 17:35:00 → SJC 2026-12-24 18:34:00.

2026-12-22 → 2026-12-24 · Axel-exclusive $553.50

• Delta Air Lines DL2904 / DL1178: SJC 2026-12-22 22:40:00 → ORD 2026-12-23 08:34:00; 1 stop(s) via ATL; 474 minutes. Local airport times.
  • DL2904: SJC 2026-12-22 22:40:00 → ATL 2026-12-23 06:10:00; layover at ATL: 75 minutes.
  • DL1178: ATL 2026-12-23 07:25:00 → ORD 2026-12-23 08:34:00.
• Delta Air Lines DL756 / DL3883: ORD 2026-12-24 14:25:00 → SJC 2026-12-24 19:25:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • DL756: ORD 2026-12-24 14:25:00 → LAX 2026-12-24 16:59:00; layover at LAX: 66 minutes.
  • DL3883: LAX 2026-12-24 18:05:00 → SJC 2026-12-24 19:25:00.

2026-12-22 → 2026-12-24 · Axel-exclusive $553.51

• Alaska Airlines AS1859 / AA2664: SJC 2026-12-22 20:24:00 → ORD 2026-12-23 05:01:00; 1 stop(s) via LAX; 397 minutes. Local airport times.
  • AS1859: SJC 2026-12-22 20:24:00 → LAX 2026-12-22 21:43:00; layover at LAX: 76 minutes.
  • AA2664: LAX 2026-12-22 22:59:00 → ORD 2026-12-23 05:01:00.
• United Airlines UA1840: ORD 2026-12-24 19:45:00 → SJC 2026-12-24 22:45:00; nonstop; 300 minutes. Local airport times.

2026-12-22 → 2026-12-24 · Axel-exclusive $600.76

• United Airlines UA1239: SJC 2026-12-22 06:30:00 → ORD 2026-12-22 12:54:00; nonstop; 264 minutes. Local airport times.
• United Airlines UA1840: ORD 2026-12-24 19:45:00 → SJC 2026-12-24 22:45:00; nonstop; 300 minutes. Local airport times.

2026-12-22 → 2026-12-24 · Axel-exclusive $553.50

• Delta Air Lines DL1254 / DL2413: SJC 2026-12-22 13:39:00 → ORD 2026-12-22 22:27:00; 1 stop(s) via SLC; 408 minutes. Local airport times.
  • DL1254: SJC 2026-12-22 13:39:00 → SLC 2026-12-22 16:40:00; layover at SLC: 95 minutes.
  • DL2413: SLC 2026-12-22 18:15:00 → ORD 2026-12-22 22:27:00.
• Delta Air Lines DL756 / DL3883: ORD 2026-12-24 14:25:00 → SJC 2026-12-24 19:25:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • DL756: ORD 2026-12-24 14:25:00 → LAX 2026-12-24 16:59:00; layover at LAX: 66 minutes.
  • DL3883: LAX 2026-12-24 18:05:00 → SJC 2026-12-24 19:25:00.

2026-12-22 → 2026-12-24 · Axel-exclusive $553.51

• Alaska Airlines AS653 / AS1478: SJC 2026-12-22 09:54:00 → ORD 2026-12-22 19:00:00; 1 stop(s) via SAN; 426 minutes. Local airport times.
  • AS653: SJC 2026-12-22 09:54:00 → SAN 2026-12-22 11:19:00; layover at SAN: 83 minutes.
  • AS1478: SAN 2026-12-22 12:42:00 → ORD 2026-12-22 19:00:00.
• United Airlines UA1840: ORD 2026-12-24 19:45:00 → SJC 2026-12-24 22:45:00; nonstop; 300 minutes. Local airport times.

2026-12-22 → 2026-12-24 · Axel-exclusive $563.63

• United Airlines UA2013 / UA1651: SJC 2026-12-22 08:45:00 → ORD 2026-12-22 18:38:00; 1 stop(s) via DEN; 473 minutes. Local airport times.
  • UA2013: SJC 2026-12-22 08:45:00 → DEN 2026-12-22 12:20:00; layover at DEN: 161 minutes.
  • UA1651: DEN 2026-12-22 15:01:00 → ORD 2026-12-22 18:38:00.
• United Airlines UA1840: ORD 2026-12-24 19:45:00 → SJC 2026-12-24 22:45:00; nonstop; 300 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 21, 2026 · Return options
• Dec 23, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Jose (SJC) to Chicago (ORD) · Dec 22, 2026 · return Dec 24, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
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