San Juan (SJU) to Chicago (ORD) · Dec 23, 2026 · return Dec 28, 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 Juan to Chicago (ORD) flight deals

2026-12-23 → 2026-12-28 · Axel-exclusive $563.75

• American Airlines AA2436: SJU 2026-12-23 05:00:00 → ORD 2026-12-23 08:39:00; nonstop; 339 minutes. Local airport times.
• American Airlines AA2571: ORD 2026-12-28 23:00:00 → SJU 2026-12-29 05:36:00; nonstop; 276 minutes. Local airport times.

2026-12-23 → 2026-12-28 · Axel-exclusive $577.50

• United Airlines UA2088: SJU 2026-12-23 16:55:00 → ORD 2026-12-23 20:26:00; nonstop; 331 minutes. Local airport times.
• United Airlines UA1996: ORD 2026-12-28 08:52:00 → SJU 2026-12-28 15:40:00; nonstop; 288 minutes. Local airport times.

2026-12-23 → 2026-12-28 · Axel-exclusive $316.25

• Frontier Airlines F91015 / F92113: SJU 2026-12-23 07:28:00 → ORD 2026-12-23 14:12:00; 1 stop(s) via PHL; 524 minutes. Local airport times.
  • F91015: SJU 2026-12-23 07:28:00 → PHL 2026-12-23 10:36:00; layover at PHL: 123 minutes.
  • F92113: PHL 2026-12-23 12:39:00 → ORD 2026-12-23 14:12:00.
• Frontier Airlines F92112 / F91726: ORD 2026-12-28 16:42:00 → SJU 2026-12-29 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
  • F92112: ORD 2026-12-28 16:42:00 → PHL 2026-12-28 20:04:00; layover at PHL: 95 minutes.
  • F91726: PHL 2026-12-28 21:39:00 → SJU 2026-12-29 02:27:00.

2026-12-23 → 2026-12-28 · Axel-exclusive $440.00

• DM DM1003 / DM5420: SJU 2026-12-23 16:24:00 → ORD 2026-12-23 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
  • DM1003: SJU 2026-12-23 16:24:00 → PUJ 2026-12-23 17:25:00; layover at PUJ: 105 minutes.
  • DM5420: PUJ 2026-12-23 19:10:00 → ORD 2026-12-23 22:20:00.
• DM DM5481 / DM1002: ORD 2026-12-28 05:45:00 → SJU 2026-12-28 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
  • DM5481: ORD 2026-12-28 05:45:00 → PUJ 2026-12-28 12:30:00; layover at PUJ: 88 minutes.
  • DM1002: PUJ 2026-12-28 13:58:00 → SJU 2026-12-28 15:03:00.

2026-12-23 → 2026-12-28 · Axel-exclusive $550.00

• Delta Air Lines DL1780 / DL2804: SJU 2026-12-23 14:55:00 → ORD 2026-12-23 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
  • DL1780: SJU 2026-12-23 14:55:00 → BOS 2026-12-23 18:11:00; layover at BOS: 149 minutes.
  • DL2804: BOS 2026-12-23 20:40:00 → ORD 2026-12-23 22:36:00.
• Delta Air Lines DL5666 / DL1961: ORD 2026-12-28 06:00:00 → SJU 2026-12-28 16:56:00; 1 stop(s) via JFK; 536 minutes. Local airport times.
  • DL5666: ORD 2026-12-28 06:00:00 → JFK 2026-12-28 09:20:00; layover at JFK: 170 minutes.
  • DL1961: JFK 2026-12-28 12:10:00 → SJU 2026-12-28 16:56:00.

2026-12-23 → 2026-12-28 · Axel-exclusive $563.75

• American Airlines AA2213: SJU 2026-12-23 15:50:00 → ORD 2026-12-23 19:29:00; nonstop; 339 minutes. Local airport times.
• American Airlines AA2571: ORD 2026-12-28 23:00:00 → SJU 2026-12-29 05:36:00; nonstop; 276 minutes. Local airport times.

2026-12-23 → 2026-12-28 · Axel-exclusive $577.50

• United Airlines UA2089: SJU 2026-12-23 08:25:00 → ORD 2026-12-23 11:47:00; nonstop; 322 minutes. Local airport times.
• United Airlines UA1996: ORD 2026-12-28 08:52:00 → SJU 2026-12-28 15:40:00; nonstop; 288 minutes. Local airport times.

2026-12-23 → 2026-12-28 · Axel-exclusive $316.25

• Frontier Airlines F92871 / F91441: SJU 2026-12-23 05:19:00 → ORD 2026-12-23 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
  • F92871: SJU 2026-12-23 05:19:00 → ATL 2026-12-23 08:26:00; layover at ATL: 131 minutes.
  • F91441: ATL 2026-12-23 10:37:00 → ORD 2026-12-23 12:00:00.
• Frontier Airlines F92112 / F91726: ORD 2026-12-28 16:42:00 → SJU 2026-12-29 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
  • F92112: ORD 2026-12-28 16:42:00 → PHL 2026-12-28 20:04:00; layover at PHL: 95 minutes.
  • F91726: PHL 2026-12-28 21:39:00 → SJU 2026-12-29 02:27:00.

2026-12-23 → 2026-12-28 · Axel-exclusive $330.25

• Frontier Airlines F94789: SJU 2026-12-23 22:26:00 → ORD 2026-12-24 01:33:00; nonstop; 307 minutes. Local airport times.
• Frontier Airlines F92112 / F91726: ORD 2026-12-28 16:42:00 → SJU 2026-12-29 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
  • F92112: ORD 2026-12-28 16:42:00 → PHL 2026-12-28 20:04:00; layover at PHL: 95 minutes.
  • F91726: PHL 2026-12-28 21:39:00 → SJU 2026-12-29 02:27:00.

2026-12-23 → 2026-12-28 · Axel-exclusive $539.25

• American Airlines AA508 / AA595: SJU 2026-12-23 08:30:00 → ORD 2026-12-23 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
  • AA508: SJU 2026-12-23 08:30:00 → PHL 2026-12-23 11:39:00; layover at PHL: 135 minutes.
  • AA595: PHL 2026-12-23 13:54:00 → ORD 2026-12-23 15:34:00.
• American Airlines AA2571: ORD 2026-12-28 23:00:00 → SJU 2026-12-29 05:36:00; nonstop; 276 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 22, 2026 · Return options
• Dec 24, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

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