San Jose (SJC) to Chicago (ORD) · Dec 14, 2026 · return Dec 19, 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 14–19, 2026 · 5 nights · 2 adults, 1 room): 3★ The Willows Hotel, $505 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $598 total · 5★ Nobu Hotel Chicago, $1,701 total

All hotels in Chicago

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

2026-12-14 → 2026-12-19 · Axel-exclusive $522.88

• United Airlines UA1239: SJC 2026-12-14 06:30:00 → ORD 2026-12-14 12:54:00; nonstop; 264 minutes. Local airport times.
• United Airlines UA1840: ORD 2026-12-19 19:45:00 → SJC 2026-12-19 22:45:00; nonstop; 300 minutes. Local airport times.

2026-12-14 → 2026-12-19 · Axel-exclusive $458.25

• American Airlines AA3257 / AA1528: SJC 2026-12-14 13:05:00 → ORD 2026-12-14 21:58:00; 1 stop(s) via PHX; 413 minutes. Local airport times.
  • AA3257: SJC 2026-12-14 13:05:00 → PHX 2026-12-14 16:05:00; layover at PHX: 81 minutes.
  • AA1528: PHX 2026-12-14 17:26:00 → ORD 2026-12-14 21:58:00.
• American Airlines AA834 / AA3113: ORD 2026-12-19 13:26:00 → SJC 2026-12-19 18:34:00; 1 stop(s) via PHX; 428 minutes. Local airport times.
  • AA834: ORD 2026-12-19 13:26:00 → PHX 2026-12-19 16:21:00; layover at PHX: 74 minutes.
  • AA3113: PHX 2026-12-19 17:35:00 → SJC 2026-12-19 18:34:00.

2026-12-14 → 2026-12-19 · Axel-exclusive $481.75

• Delta Air Lines DL2904 / DL1178: SJC 2026-12-14 22:40:00 → ORD 2026-12-15 08:34:00; 1 stop(s) via ATL; 474 minutes. Local airport times.
  • DL2904: SJC 2026-12-14 22:40:00 → ATL 2026-12-15 06:10:00; layover at ATL: 75 minutes.
  • DL1178: ATL 2026-12-15 07:25:00 → ORD 2026-12-15 08:34:00.
• Delta Air Lines DL756 / DL3883: ORD 2026-12-19 14:25:00 → SJC 2026-12-19 19:25:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • DL756: ORD 2026-12-19 14:25:00 → LAX 2026-12-19 16:59:00; layover at LAX: 66 minutes.
  • DL3883: LAX 2026-12-19 18:05:00 → SJC 2026-12-19 19:25:00.

2026-12-14 → 2026-12-19 · Axel-exclusive $487.88

• Alaska Airlines AS653 / AS1478: SJC 2026-12-14 09:54:00 → ORD 2026-12-14 19:00:00; 1 stop(s) via SAN; 426 minutes. Local airport times.
  • AS653: SJC 2026-12-14 09:54:00 → SAN 2026-12-14 11:19:00; layover at SAN: 83 minutes.
  • AS1478: SAN 2026-12-14 12:42:00 → ORD 2026-12-14 19:00:00.
• United Airlines UA1840: ORD 2026-12-19 19:45:00 → SJC 2026-12-19 22:45:00; nonstop; 300 minutes. Local airport times.

2026-12-14 → 2026-12-19 · Axel-exclusive $522.88

• United Airlines UA1082: SJC 2026-12-14 14:11:00 → ORD 2026-12-14 20:30:00; nonstop; 259 minutes. Local airport times.
• United Airlines UA1840: ORD 2026-12-19 19:45:00 → SJC 2026-12-19 22:45:00; nonstop; 300 minutes. Local airport times.

2026-12-14 → 2026-12-19 · Axel-exclusive $481.75

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

2026-12-14 → 2026-12-19 · Axel-exclusive $487.88

• Alaska Airlines AS1859 / AA2664: SJC 2026-12-14 20:24:00 → ORD 2026-12-15 05:01:00; 1 stop(s) via LAX; 397 minutes. Local airport times.
  • AS1859: SJC 2026-12-14 20:24:00 → LAX 2026-12-14 21:43:00; layover at LAX: 76 minutes.
  • AA2664: LAX 2026-12-14 22:59:00 → ORD 2026-12-15 05:01:00.
• United Airlines UA1840: ORD 2026-12-19 19:45:00 → SJC 2026-12-19 22:45:00; nonstop; 300 minutes. Local airport times.

2026-12-14 → 2026-12-19 · Axel-exclusive $495.38

• United Airlines UA2013 / UA1651: SJC 2026-12-14 08:45:00 → ORD 2026-12-14 18:38:00; 1 stop(s) via DEN; 473 minutes. Local airport times.
  • UA2013: SJC 2026-12-14 08:45:00 → DEN 2026-12-14 12:20:00; layover at DEN: 161 minutes.
  • UA1651: DEN 2026-12-14 15:01:00 → ORD 2026-12-14 18:38:00.
• United Airlines UA1840: ORD 2026-12-19 19:45:00 → SJC 2026-12-19 22:45:00; nonstop; 300 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 13, 2026 · Return options
• Dec 15, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Jose (SJC) to Chicago (ORD) · Dec 14, 2026 · return Dec 19, 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.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
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• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel San Francisco Bay Area to Chicago (ORD) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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