San Jose (SJC) to Chicago (ORD), Nov 7–17, 2026: from $390 round trip

San Jose (SJC) to Chicago (ORD), Nov 7–17, 2026: from $390 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $390 round trip, Axel-exclusive, American Airlines, 1 stop, Nov 7–17, 2026, 1 adult, economy, checked Oct 29, 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 link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Nov 7–17, 2026 · 10 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $1,762 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $770 total · 5★ Nobu Hotel Chicago, $5,707 total

All hotels in Chicago

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

2026-11-07 → 2026-11-17 · Axel-exclusive $390.00

• American Airlines AA3257 / AA1528: SJC 2026-11-07 13:05:00 → ORD 2026-11-07 21:58:00; 1 stop(s) via PHX; 413 minutes. Local airport times.
  • AA3257: SJC 2026-11-07 13:05:00 → PHX 2026-11-07 16:05:00; layover at PHX: 81 minutes.
  • AA1528: PHX 2026-11-07 17:26:00 → ORD 2026-11-07 21:58:00.
• American Airlines AA3111 / AS672: ORD 2026-11-17 16:45:00 → SJC 2026-11-17 22:56:00; 1 stop(s) via SAN; 491 minutes. Local airport times.
  • AA3111: ORD 2026-11-17 16:45:00 → SAN 2026-11-17 19:18:00; layover at SAN: 121 minutes.
  • AS672: SAN 2026-11-17 21:19:00 → SJC 2026-11-17 22:56:00.

2026-11-07 → 2026-11-17 · Axel-exclusive $390.00

• United Airlines UA2013 / UA1651: SJC 2026-11-07 08:45:00 → ORD 2026-11-07 18:38:00; 1 stop(s) via DEN; 473 minutes. Local airport times.
  • UA2013: SJC 2026-11-07 08:45:00 → DEN 2026-11-07 12:20:00; layover at DEN: 161 minutes.
  • UA1651: DEN 2026-11-07 15:01:00 → ORD 2026-11-07 18:38:00.
• United Airlines UA2495 / UA1256: ORD 2026-11-17 08:40:00 → SJC 2026-11-17 13:18:00; 1 stop(s) via DEN; 398 minutes. Local airport times.
  • UA2495: ORD 2026-11-17 08:40:00 → DEN 2026-11-17 10:26:00; layover at DEN: 69 minutes.
  • UA1256: DEN 2026-11-17 11:35:00 → SJC 2026-11-17 13:18:00.

2026-11-07 → 2026-11-17 · Axel-exclusive $392.50

• Alaska Airlines AS1859 / AA2664: SJC 2026-11-07 20:24:00 → ORD 2026-11-08 05:01:00; 1 stop(s) via LAX; 397 minutes. Local airport times.
  • AS1859: SJC 2026-11-07 20:24:00 → LAX 2026-11-07 21:43:00; layover at LAX: 76 minutes.
  • AA2664: LAX 2026-11-07 22:59:00 → ORD 2026-11-08 05:01:00.
• Delta Air Lines DL1477 / DL933: ORD 2026-11-17 15:59:00 → SJC 2026-11-17 22:12:00; 1 stop(s) via ATL; 493 minutes. Local airport times.
  • DL1477: ORD 2026-11-17 15:59:00 → ATL 2026-11-17 18:54:00; layover at ATL: 65 minutes.
  • DL933: ATL 2026-11-17 19:59:00 → SJC 2026-11-17 22:12:00.

2026-11-07 → 2026-11-17 · Axel-exclusive $410.00

• Delta Air Lines DL1254 / DL2413: SJC 2026-11-07 13:39:00 → ORD 2026-11-07 22:27:00; 1 stop(s) via SLC; 408 minutes. Local airport times.
  • DL1254: SJC 2026-11-07 13:39:00 → SLC 2026-11-07 16:40:00; layover at SLC: 95 minutes.
  • DL2413: SLC 2026-11-07 18:15:00 → ORD 2026-11-07 22:27:00.
• Delta Air Lines DL1477 / DL933: ORD 2026-11-17 15:59:00 → SJC 2026-11-17 22:12:00; 1 stop(s) via ATL; 493 minutes. Local airport times.
  • DL1477: ORD 2026-11-17 15:59:00 → ATL 2026-11-17 18:54:00; layover at ATL: 65 minutes.
  • DL933: ATL 2026-11-17 19:59:00 → SJC 2026-11-17 22:12:00.

2026-11-07 → 2026-11-17 · Axel-exclusive $410.00

• Delta Air Lines DL2904 / DL1178: SJC 2026-11-07 22:40:00 → ORD 2026-11-08 08:34:00; 1 stop(s) via ATL; 474 minutes. Local airport times.
  • DL2904: SJC 2026-11-07 22:40:00 → ATL 2026-11-08 06:10:00; layover at ATL: 75 minutes.
  • DL1178: ATL 2026-11-08 07:25:00 → ORD 2026-11-08 08:34:00.
• Delta Air Lines DL1477 / DL933: ORD 2026-11-17 15:59:00 → SJC 2026-11-17 22:12:00; 1 stop(s) via ATL; 493 minutes. Local airport times.
  • DL1477: ORD 2026-11-17 15:59:00 → ATL 2026-11-17 18:54:00; layover at ATL: 65 minutes.
  • DL933: ATL 2026-11-17 19:59:00 → SJC 2026-11-17 22:12:00.

2026-11-07 → 2026-11-17 · Axel-exclusive $417.50

• United Airlines UA2382: SJC 2026-11-07 23:00:00 → ORD 2026-11-08 05:17:00; nonstop; 257 minutes. Local airport times.
• United Airlines UA2495 / UA1256: ORD 2026-11-17 08:40:00 → SJC 2026-11-17 13:18:00; 1 stop(s) via DEN; 398 minutes. Local airport times.
  • UA2495: ORD 2026-11-17 08:40:00 → DEN 2026-11-17 10:26:00; layover at DEN: 69 minutes.
  • UA1256: DEN 2026-11-17 11:35:00 → SJC 2026-11-17 13:18:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Nov 8, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Jose (SJC) to Chicago (ORD) · Nov 7, 2026 · return Nov 17, 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 link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
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