San Jose (SJC) to Chicago (ORD), Jan 16–23, 2027: from $371 round trip

Lowest published fare: $371 round trip, Axel-exclusive, American Airlines, 1 stop, Jan 16–23, 2027, 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.

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

2027-01-16 → 2027-01-23 · Axel-exclusive $422.76

• United Airlines UA1082: SJC 2027-01-16 14:11:00 → ORD 2027-01-16 20:30:00; nonstop; 259 minutes. Local airport times.
• United Airlines UA1840: ORD 2027-01-23 19:45:00 → SJC 2027-01-23 22:45:00; nonstop; 300 minutes. Local airport times.

2027-01-16 → 2027-01-23 · Axel-exclusive $370.50

• American Airlines AA3257 / AA1528: SJC 2027-01-16 13:05:00 → ORD 2027-01-16 21:58:00; 1 stop(s) via PHX; 413 minutes. Local airport times.
  • AA3257: SJC 2027-01-16 13:05:00 → PHX 2027-01-16 16:05:00; layover at PHX: 81 minutes.
  • AA1528: PHX 2027-01-16 17:26:00 → ORD 2027-01-16 21:58:00.
• American Airlines AA834 / AA3113: ORD 2027-01-23 13:26:00 → SJC 2027-01-23 18:34:00; 1 stop(s) via PHX; 428 minutes. Local airport times.
  • AA834: ORD 2027-01-23 13:26:00 → PHX 2027-01-23 16:21:00; layover at PHX: 74 minutes.
  • AA3113: PHX 2027-01-23 17:35:00 → SJC 2027-01-23 18:34:00.

2027-01-16 → 2027-01-23 · Axel-exclusive $389.50

• Delta Air Lines DL1254 / DL2413: SJC 2027-01-16 13:39:00 → ORD 2027-01-16 22:27:00; 1 stop(s) via SLC; 408 minutes. Local airport times.
  • DL1254: SJC 2027-01-16 13:39:00 → SLC 2027-01-16 16:40:00; layover at SLC: 95 minutes.
  • DL2413: SLC 2027-01-16 18:15:00 → ORD 2027-01-16 22:27:00.
• Delta Air Lines DL756 / DL3883: ORD 2027-01-23 14:25:00 → SJC 2027-01-23 19:25:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • DL756: ORD 2027-01-23 14:25:00 → LAX 2027-01-23 16:59:00; layover at LAX: 66 minutes.
  • DL3883: LAX 2027-01-23 18:05:00 → SJC 2027-01-23 19:25:00.

2027-01-16 → 2027-01-23 · Axel-exclusive $389.51

• Alaska Airlines AS1859 / AA2664: SJC 2027-01-16 20:24:00 → ORD 2027-01-17 05:01:00; 1 stop(s) via LAX; 397 minutes. Local airport times.
  • AS1859: SJC 2027-01-16 20:24:00 → LAX 2027-01-16 21:43:00; layover at LAX: 76 minutes.
  • AA2664: LAX 2027-01-16 22:59:00 → ORD 2027-01-17 05:01:00.
• United Airlines UA1840: ORD 2027-01-23 19:45:00 → SJC 2027-01-23 22:45:00; nonstop; 300 minutes. Local airport times.

2027-01-16 → 2027-01-23 · Axel-exclusive $422.76

• United Airlines UA2382: SJC 2027-01-16 23:00:00 → ORD 2027-01-17 05:17:00; nonstop; 257 minutes. Local airport times.
• United Airlines UA1840: ORD 2027-01-23 19:45:00 → SJC 2027-01-23 22:45:00; nonstop; 300 minutes. Local airport times.

2027-01-16 → 2027-01-23 · Axel-exclusive $389.50

• Delta Air Lines DL2904 / DL1178: SJC 2027-01-16 22:40:00 → ORD 2027-01-17 08:34:00; 1 stop(s) via ATL; 474 minutes. Local airport times.
  • DL2904: SJC 2027-01-16 22:40:00 → ATL 2027-01-17 06:10:00; layover at ATL: 75 minutes.
  • DL1178: ATL 2027-01-17 07:25:00 → ORD 2027-01-17 08:34:00.
• Delta Air Lines DL756 / DL3883: ORD 2027-01-23 14:25:00 → SJC 2027-01-23 19:25:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • DL756: ORD 2027-01-23 14:25:00 → LAX 2027-01-23 16:59:00; layover at LAX: 66 minutes.
  • DL3883: LAX 2027-01-23 18:05:00 → SJC 2027-01-23 19:25:00.

2027-01-16 → 2027-01-23 · Axel-exclusive $389.51

• Alaska Airlines AS653 / AS1478: SJC 2027-01-16 09:54:00 → ORD 2027-01-16 19:00:00; 1 stop(s) via SAN; 426 minutes. Local airport times.
  • AS653: SJC 2027-01-16 09:54:00 → SAN 2027-01-16 11:19:00; layover at SAN: 83 minutes.
  • AS1478: SAN 2027-01-16 12:42:00 → ORD 2027-01-16 19:00:00.
• United Airlines UA1840: ORD 2027-01-23 19:45:00 → SJC 2027-01-23 22:45:00; nonstop; 300 minutes. Local airport times.

2027-01-16 → 2027-01-23 · Axel-exclusive $396.63

• United Airlines UA2013 / UA1651: SJC 2027-01-16 08:45:00 → ORD 2027-01-16 18:38:00; 1 stop(s) via DEN; 473 minutes. Local airport times.
  • UA2013: SJC 2027-01-16 08:45:00 → DEN 2027-01-16 12:20:00; layover at DEN: 161 minutes.
  • UA1651: DEN 2027-01-16 15:01:00 → ORD 2027-01-16 18:38:00.
• United Airlines UA1840: ORD 2027-01-23 19:45:00 → SJC 2027-01-23 22:45:00; nonstop; 300 minutes. Local airport times.

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
• Jan 15, 2027 · Return options
• Jan 17, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

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