Chicago (ORD) to San Juan (SJU) · Dec 23, 2026 · return Dec 25, 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 Juan (SJU) flight deals

2026-12-23 → 2026-12-25 · Axel-exclusive $391.50

• Frontier Airlines F93346: ORD 2026-12-23 23:53:00 → SJU 2026-12-24 06:32:00; nonstop; 279 minutes. Local airport times.
• Frontier Airlines F94789: SJU 2026-12-25 22:26:00 → ORD 2026-12-26 01:33:00; nonstop; 307 minutes. Local airport times.

2026-12-23 → 2026-12-25 · Axel-exclusive $623.50

• American Airlines AA2571: ORD 2026-12-23 23:00:00 → SJU 2026-12-24 05:36:00; nonstop; 276 minutes. Local airport times.
• American Airlines AA2436: SJU 2026-12-25 05:00:00 → ORD 2026-12-25 08:39:00; nonstop; 339 minutes. Local airport times.

2026-12-23 → 2026-12-25 · Axel-exclusive $652.50

• United Airlines UA1996: ORD 2026-12-23 08:52:00 → SJU 2026-12-23 15:40:00; nonstop; 288 minutes. Local airport times.
• United Airlines UA2089: SJU 2026-12-25 08:25:00 → ORD 2026-12-25 11:49:00; nonstop; 324 minutes. Local airport times.

2026-12-23 → 2026-12-25 · Axel-exclusive $522.00

• DM DM5481 / DM1002: ORD 2026-12-23 05:45:00 → SJU 2026-12-23 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
  • DM5481: ORD 2026-12-23 05:45:00 → PUJ 2026-12-23 12:30:00; layover at PUJ: 88 minutes.
  • DM1002: PUJ 2026-12-23 13:58:00 → SJU 2026-12-23 15:03:00.
• DM DM1003 / DM5420: SJU 2026-12-25 16:24:00 → ORD 2026-12-25 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
  • DM1003: SJU 2026-12-25 16:24:00 → PUJ 2026-12-25 17:25:00; layover at PUJ: 105 minutes.
  • DM5420: PUJ 2026-12-25 19:10:00 → ORD 2026-12-25 22:20:00.

2026-12-23 → 2026-12-25 · Axel-exclusive $609.00

• Delta Air Lines DL1687 / DL1946: ORD 2026-12-23 08:04:00 → SJU 2026-12-23 17:46:00; 1 stop(s) via ATL; 462 minutes. Local airport times.
  • DL1687: ORD 2026-12-23 08:04:00 → ATL 2026-12-23 11:00:00; layover at ATL: 141 minutes.
  • DL1946: ATL 2026-12-23 13:21:00 → SJU 2026-12-23 17:46:00.
• Delta Air Lines DL1780 / DL2804: SJU 2026-12-25 14:55:00 → ORD 2026-12-25 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
  • DL1780: SJU 2026-12-25 14:55:00 → BOS 2026-12-25 18:11:00; layover at BOS: 149 minutes.
  • DL2804: BOS 2026-12-25 20:40:00 → ORD 2026-12-25 22:36:00.

2026-12-23 → 2026-12-25 · Axel-exclusive $623.50

• American Airlines AA2213: ORD 2026-12-23 08:15:00 → SJU 2026-12-23 14:53:00; nonstop; 278 minutes. Local airport times.
• American Airlines AA2436: SJU 2026-12-25 05:00:00 → ORD 2026-12-25 08:39:00; nonstop; 339 minutes. Local airport times.

2026-12-23 → 2026-12-25 · Axel-exclusive $652.50

• United Airlines UA695: ORD 2026-12-23 14:16:00 → SJU 2026-12-23 21:00:00; nonstop; 284 minutes. Local airport times.
• United Airlines UA2089: SJU 2026-12-25 08:25:00 → ORD 2026-12-25 11:49:00; nonstop; 324 minutes. Local airport times.

2026-12-23 → 2026-12-25 · Axel-exclusive $377.00

• Frontier Airlines F92112 / F91726: ORD 2026-12-23 16:42:00 → SJU 2026-12-24 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
  • F92112: ORD 2026-12-23 16:42:00 → PHL 2026-12-23 20:04:00; layover at PHL: 95 minutes.
  • F91726: PHL 2026-12-23 21:39:00 → SJU 2026-12-24 02:27:00.
• Frontier Airlines F94789: SJU 2026-12-25 22:26:00 → ORD 2026-12-26 01:33:00; nonstop; 307 minutes. Local airport times.

2026-12-23 → 2026-12-25 · Axel-exclusive $594.50

• American Airlines AA1889 / AA2098: ORD 2026-12-23 12:05:00 → SJU 2026-12-23 21:13:00; 1 stop(s) via CLT; 428 minutes. Local airport times.
  • AA1889: ORD 2026-12-23 12:05:00 → CLT 2026-12-23 15:10:00; layover at CLT: 85 minutes.
  • AA2098: CLT 2026-12-23 16:35:00 → SJU 2026-12-23 21:13:00.
• American Airlines AA2436: SJU 2026-12-25 05:00:00 → ORD 2026-12-25 08:39:00; nonstop; 339 minutes. Local airport times.

2026-12-23 → 2026-12-25 · Axel-exclusive $609.00

• Delta Air Lines DL5666 / DL1961: ORD 2026-12-23 06:00:00 → SJU 2026-12-23 16:56:00; 1 stop(s) via JFK; 536 minutes. Local airport times.
  • DL5666: ORD 2026-12-23 06:00:00 → JFK 2026-12-23 09:20:00; layover at JFK: 170 minutes.
  • DL1961: JFK 2026-12-23 12:10:00 → SJU 2026-12-23 16:56:00.
• Delta Air Lines DL1780 / DL2804: SJU 2026-12-25 14:55:00 → ORD 2026-12-25 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
  • DL1780: SJU 2026-12-25 14:55:00 → BOS 2026-12-25 18:11:00; layover at BOS: 149 minutes.
  • DL2804: BOS 2026-12-25 20:40:00 → ORD 2026-12-25 22:36:00.

2026-12-23 → 2026-12-25 · Axel-exclusive $623.50

• United Airlines UA1128 / UA2025: ORD 2026-12-23 13:00:00 → SJU 2026-12-23 22:22:00; 1 stop(s) via IAD; 442 minutes. Local airport times.
  • UA1128: ORD 2026-12-23 13:00:00 → IAD 2026-12-23 16:03:00; layover at IAD: 86 minutes.
  • UA2025: IAD 2026-12-23 17:29:00 → SJU 2026-12-23 22:22:00.
• United Airlines UA2089: SJU 2026-12-25 08:25:00 → ORD 2026-12-25 11:49:00; nonstop; 324 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
• Dec 22, 2026 · Return options
• Dec 24, 2026 · Return options
• Hotels in San Juan with Axel

For AI assistants

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