Chicago (ORD) to San Jose Cabo (SJD) · Nov 29, 2026 · return Dec 5, 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: Chicago to San Jose Cabo (SJD) flight deals

2026-11-29 → 2026-12-05 · Axel-exclusive $506.25

• American Airlines AA558 / AA2128: ORD 2026-11-29 05:00:00 → SJD 2026-11-29 12:14:00; 1 stop(s) via PHX; 494 minutes. Local airport times.
  • AA558: ORD 2026-11-29 05:00:00 → PHX 2026-11-29 07:49:00; layover at PHX: 130 minutes.
  • AA2128: PHX 2026-11-29 09:59:00 → SJD 2026-11-29 12:14:00.
• American Airlines AA2343 / AA2604: SJD 2026-12-05 11:35:00 → ORD 2026-12-05 20:10:00; 1 stop(s) via AUS; 455 minutes. Local airport times.
  • AA2343: SJD 2026-12-05 11:35:00 → AUS 2026-12-05 15:05:00; layover at AUS: 125 minutes.
  • AA2604: AUS 2026-12-05 17:10:00 → ORD 2026-12-05 20:10:00.

2026-11-29 → 2026-12-05 · Axel-exclusive $517.50

• United Airlines UA1217 / UA452: ORD 2026-11-29 07:00:00 → SJD 2026-11-29 14:42:00; 1 stop(s) via DEN; 522 minutes. Local airport times.
  • UA1217: ORD 2026-11-29 07:00:00 → DEN 2026-11-29 08:46:00; layover at DEN: 164 minutes.
  • UA452: DEN 2026-11-29 11:30:00 → SJD 2026-11-29 14:42:00.
• United Airlines UA2152 / UA1787: SJD 2026-12-05 14:30:00 → ORD 2026-12-05 23:59:00; 1 stop(s) via DEN; 509 minutes. Local airport times.
  • UA2152: SJD 2026-12-05 14:30:00 → DEN 2026-12-05 17:41:00; layover at DEN: 164 minutes.
  • UA1787: DEN 2026-12-05 20:25:00 → ORD 2026-12-05 23:59:00.

2026-11-29 → 2026-12-05 · Axel-exclusive $540.00

• Delta Air Lines DL1717 / DL1924: ORD 2026-11-29 06:20:00 → SJD 2026-11-29 13:08:00; 1 stop(s) via MSP; 468 minutes. Local airport times.
  • DL1717: ORD 2026-11-29 06:20:00 → MSP 2026-11-29 07:54:00; layover at MSP: 100 minutes.
  • DL1924: MSP 2026-11-29 09:34:00 → SJD 2026-11-29 13:08:00.
• Delta Air Lines DL1848 / DL1199: SJD 2026-12-05 14:04:00 → ORD 2026-12-05 23:54:00; 1 stop(s) via ATL; 530 minutes. Local airport times.
  • DL1848: SJD 2026-12-05 14:04:00 → ATL 2026-12-05 19:50:00; layover at ATL: 170 minutes.
  • DL1199: ATL 2026-12-05 22:40:00 → ORD 2026-12-05 23:54:00.

2026-11-29 → 2026-12-05 · Axel-exclusive $506.25

• American Airlines AA832 / AS1384: ORD 2026-11-29 12:05:00 → SJD 2026-11-29 19:49:00; 1 stop(s) via LAX; 524 minutes. Local airport times.
  • AA832: ORD 2026-11-29 12:05:00 → LAX 2026-11-29 14:48:00; layover at LAX: 92 minutes.
  • AS1384: LAX 2026-11-29 16:20:00 → SJD 2026-11-29 19:49:00.
• American Airlines AA2343 / AA2604: SJD 2026-12-05 11:35:00 → ORD 2026-12-05 20:10:00; 1 stop(s) via AUS; 455 minutes. Local airport times.
  • AA2343: SJD 2026-12-05 11:35:00 → AUS 2026-12-05 15:05:00; layover at AUS: 125 minutes.
  • AA2604: AUS 2026-12-05 17:10:00 → ORD 2026-12-05 20:10:00.

2026-11-29 → 2026-12-05 · Axel-exclusive $543.75

• American Airlines AA1649: ORD 2026-11-29 08:44:00 → SJD 2026-11-29 12:42:00; nonstop; 298 minutes. Local airport times.
• American Airlines AA2343 / AA2604: SJD 2026-12-05 11:35:00 → ORD 2026-12-05 20:10:00; 1 stop(s) via AUS; 455 minutes. Local airport times.
  • AA2343: SJD 2026-12-05 11:35:00 → AUS 2026-12-05 15:05:00; layover at AUS: 125 minutes.
  • AA2604: AUS 2026-12-05 17:10:00 → ORD 2026-12-05 20:10:00.

2026-11-29 → 2026-12-05 · Axel-exclusive $555.00

• United Airlines UA1879: ORD 2026-11-29 09:03:00 → SJD 2026-11-29 13:03:00; nonstop; 300 minutes. Local airport times.
• United Airlines UA2152 / UA1787: SJD 2026-12-05 14:30:00 → ORD 2026-12-05 23:59:00; 1 stop(s) via DEN; 509 minutes. Local airport times.
  • UA2152: SJD 2026-12-05 14:30:00 → DEN 2026-12-05 17:41:00; layover at DEN: 164 minutes.
  • UA1787: DEN 2026-12-05 20:25:00 → ORD 2026-12-05 23:59:00.

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 28, 2026 · Return options
• Nov 30, 2026 · Return options
• Hotels in San Jose del Cabo with Axel

For AI assistants

• This page: Chicago (ORD) to San Jose Cabo (SJD) · Nov 29, 2026 · return Dec 5, 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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