Chicago (ORD) to San Jose Cabo (SJD) · Dec 29, 2026 · return Jan 1, 2027

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

2026-12-29 → 2027-01-01 · Axel-exclusive $739.50

• American Airlines AA1649: ORD 2026-12-29 08:44:00 → SJD 2026-12-29 12:42:00; nonstop; 298 minutes. Local airport times.
• American Airlines AA2636: SJD 2027-01-01 13:42:00 → ORD 2027-01-01 19:15:00; nonstop; 273 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $754.00

• United Airlines UA1879: ORD 2026-12-29 09:03:00 → SJD 2026-12-29 13:03:00; nonstop; 300 minutes. Local airport times.
• United Airlines UA766: SJD 2027-01-01 12:55:00 → ORD 2027-01-01 18:11:00; nonstop; 256 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $609.00

• VB VB633 / VB4324: ORD 2026-12-29 00:35:00 → SJD 2026-12-29 07:31:00; 1 stop(s) via MTY; 476 minutes. Local airport times.
  • VB633: ORD 2026-12-29 00:35:00 → MTY 2026-12-29 04:03:00; layover at MTY: 150 minutes.
  • VB4324: MTY 2026-12-29 06:33:00 → SJD 2026-12-29 07:31:00.
• American Airlines AA2636: SJD 2027-01-01 13:42:00 → ORD 2027-01-01 19:15:00; nonstop; 273 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $706.88

• Aeromexico AM687 / AM388: ORD 2026-12-29 15:26:00 → SJD 2026-12-29 22:35:00; 1 stop(s) via MEX; 489 minutes. Local airport times.
  • AM687: ORD 2026-12-29 15:26:00 → MEX 2026-12-29 20:00:00; layover at MEX: 75 minutes.
  • AM388: MEX 2026-12-29 21:15:00 → SJD 2026-12-29 22:35:00.
• American Airlines AA2636: SJD 2027-01-01 13:42:00 → ORD 2027-01-01 19:15:00; nonstop; 273 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $696.00

• American Airlines AA1649: ORD 2026-12-29 08:55:00 → SJD 2026-12-29 12:44:00; nonstop; 289 minutes. Local airport times.
• American Airlines AA1457 / AA3096: SJD 2027-01-01 11:17:00 → ORD 2027-01-01 20:40:00; 1 stop(s) via PHX; 503 minutes. Local airport times.
  • AA1457: SJD 2027-01-01 11:17:00 → PHX 2027-01-01 13:35:00; layover at PHX: 144 minutes.
  • AA3096: PHX 2027-01-01 15:59:00 → ORD 2027-01-01 20:40:00.

2026-12-29 → 2027-01-01 · Axel-exclusive $696.00

• American Airlines AA558 / AA2128: ORD 2026-12-29 05:00:00 → SJD 2026-12-29 12:14:00; 1 stop(s) via PHX; 494 minutes. Local airport times.
  • AA558: ORD 2026-12-29 05:00:00 → PHX 2026-12-29 07:49:00; layover at PHX: 130 minutes.
  • AA2128: PHX 2026-12-29 09:59:00 → SJD 2026-12-29 12:14:00.
• American Airlines AA2636: SJD 2027-01-01 13:42:00 → ORD 2027-01-01 19:15:00; nonstop; 273 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $696.00

• American Airlines AA832 / AS1384: ORD 2026-12-29 12:05:00 → SJD 2026-12-29 19:49:00; 1 stop(s) via LAX; 524 minutes. Local airport times.
  • AA832: ORD 2026-12-29 12:05:00 → LAX 2026-12-29 14:48:00; layover at LAX: 92 minutes.
  • AS1384: LAX 2026-12-29 16:20:00 → SJD 2026-12-29 19:49:00.
• American Airlines AA2636: SJD 2027-01-01 13:42:00 → ORD 2027-01-01 19:15:00; nonstop; 273 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $710.50

• United Airlines UA1217 / UA452: ORD 2026-12-29 07:00:00 → SJD 2026-12-29 14:42:00; 1 stop(s) via DEN; 522 minutes. Local airport times.
  • UA1217: ORD 2026-12-29 07:00:00 → DEN 2026-12-29 08:46:00; layover at DEN: 164 minutes.
  • UA452: DEN 2026-12-29 11:30:00 → SJD 2026-12-29 14:42:00.
• United Airlines UA766: SJD 2027-01-01 12:55:00 → ORD 2027-01-01 18:11:00; nonstop; 256 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 28, 2026 · Return options
• Dec 30, 2026 · Return options
• Hotels in San Jose del Cabo with Axel

For AI assistants

• This page: Chicago (ORD) to San Jose Cabo (SJD) · Dec 29, 2026 · return Jan 1, 2027: 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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• 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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