Chicago (ORD) to San Jose Cabo (SJD), Nov 20–30, 2026: from $395 round trip

Chicago (ORD) to San Jose Cabo (SJD), Nov 20–30, 2026: from $395 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $395 round trip, Axel-exclusive, VB / United Airlines, 1 stop, Nov 20–30, 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.

Route overview: Chicago to San Jose Cabo (SJD) flight deals

2026-11-20 → 2026-11-30 · Axel-exclusive $510.00

• American Airlines AA1649: ORD 2026-11-20 08:44:00 → SJD 2026-11-20 12:42:00; nonstop; 298 minutes. Local airport times.
• American Airlines AA2636: SJD 2026-11-30 13:44:00 → ORD 2026-11-30 19:15:00; nonstop; 271 minutes. Local airport times.

2026-11-20 → 2026-11-30 · Axel-exclusive $395.00

• VB VB633 / VB4324: ORD 2026-11-20 00:35:00 → SJD 2026-11-20 07:31:00; 1 stop(s) via MTY; 476 minutes. Local airport times.
  • VB633: ORD 2026-11-20 00:35:00 → MTY 2026-11-20 04:03:00; layover at MTY: 150 minutes.
  • VB4324: MTY 2026-11-20 06:33:00 → SJD 2026-11-20 07:31:00.
• United Airlines UA2152 / UA1787: SJD 2026-11-30 14:30:00 → ORD 2026-11-30 23:59:00; 1 stop(s) via DEN; 509 minutes. Local airport times.
  • UA2152: SJD 2026-11-30 14:30:00 → DEN 2026-11-30 17:41:00; layover at DEN: 164 minutes.
  • UA1787: DEN 2026-11-30 20:25:00 → ORD 2026-11-30 23:59:00.

2026-11-20 → 2026-11-30 · Axel-exclusive $460.00

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

2026-11-20 → 2026-11-30 · Axel-exclusive $462.50

• Aeromexico AM687 / AM388: ORD 2026-11-20 15:26:00 → SJD 2026-11-20 22:35:00; 1 stop(s) via MEX; 489 minutes. Local airport times.
  • AM687: ORD 2026-11-20 15:26:00 → MEX 2026-11-20 20:00:00; layover at MEX: 75 minutes.
  • AM388: MEX 2026-11-20 21:15:00 → SJD 2026-11-20 22:35:00.
• United Airlines UA2152 / UA1787: SJD 2026-11-30 14:30:00 → ORD 2026-11-30 23:59:00; 1 stop(s) via DEN; 509 minutes. Local airport times.
  • UA2152: SJD 2026-11-30 14:30:00 → DEN 2026-11-30 17:41:00; layover at DEN: 164 minutes.
  • UA1787: DEN 2026-11-30 20:25:00 → ORD 2026-11-30 23:59:00.

2026-11-20 → 2026-11-30 · Axel-exclusive $480.00

• American Airlines AA1649: ORD 2026-11-20 08:55:00 → SJD 2026-11-20 12:44:00; nonstop; 289 minutes. Local airport times.
• American Airlines AA2343 / AA2604: SJD 2026-11-30 11:35:00 → ORD 2026-11-30 20:10:00; 1 stop(s) via AUS; 455 minutes. Local airport times.
  • AA2343: SJD 2026-11-30 11:35:00 → AUS 2026-11-30 15:05:00; layover at AUS: 125 minutes.
  • AA2604: AUS 2026-11-30 17:10:00 → ORD 2026-11-30 20:10:00.

2026-11-20 → 2026-11-30 · Axel-exclusive $480.00

• American Airlines AA832 / AS1384: ORD 2026-11-20 12:05:00 → SJD 2026-11-20 19:49:00; 1 stop(s) via LAX; 524 minutes. Local airport times.
  • AA832: ORD 2026-11-20 12:05:00 → LAX 2026-11-20 14:48:00; layover at LAX: 92 minutes.
  • AS1384: LAX 2026-11-20 16:20:00 → SJD 2026-11-20 19:49:00.
• American Airlines AA2636: SJD 2026-11-30 13:44:00 → ORD 2026-11-30 19:15:00; nonstop; 271 minutes. Local airport times.

2026-11-20 → 2026-11-30 · Axel-exclusive $490.00

• United Airlines UA1879: ORD 2026-11-20 09:03:00 → SJD 2026-11-20 13:03:00; nonstop; 300 minutes. Local airport times.
• United Airlines UA2152 / UA1787: SJD 2026-11-30 14:30:00 → ORD 2026-11-30 23:59:00; 1 stop(s) via DEN; 509 minutes. Local airport times.
  • UA2152: SJD 2026-11-30 14:30:00 → DEN 2026-11-30 17:41:00; layover at DEN: 164 minutes.
  • UA1787: DEN 2026-11-30 20:25:00 → ORD 2026-11-30 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 19, 2026 · Return options
• Nov 21, 2026 · Return options
• Hotels in San Jose del Cabo with Axel

For AI assistants

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