San Juan (SJU) to Chicago (ORD) · Dec 1, 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: San Juan to Chicago (ORD) flight deals

2026-12-01 → 2026-12-05 · Axel-exclusive $250.00

• Frontier Airlines F93345: SJU 2026-12-01 19:12:00 → ORD 2026-12-01 22:21:00; nonstop; 309 minutes. Local airport times.
• Frontier Airlines F93346: ORD 2026-12-05 23:53:00 → SJU 2026-12-06 06:32:00; nonstop; 279 minutes. Local airport times.

2026-12-01 → 2026-12-05 · Axel-exclusive $410.00

• American Airlines AA2213: SJU 2026-12-01 15:50:00 → ORD 2026-12-01 19:29:00; nonstop; 339 minutes. Local airport times.
• American Airlines AA1555: ORD 2026-12-05 17:01:00 → SJU 2026-12-05 23:39:00; nonstop; 278 minutes. Local airport times.

2026-12-01 → 2026-12-05 · Axel-exclusive $420.00

• United Airlines UA2088: SJU 2026-12-01 16:55:00 → ORD 2026-12-01 20:26:00; nonstop; 331 minutes. Local airport times.
• United Airlines UA1996: ORD 2026-12-05 08:52:00 → SJU 2026-12-05 15:40:00; nonstop; 288 minutes. Local airport times.

2026-12-01 → 2026-12-05 · Axel-exclusive $320.00

• DM DM1003 / DM5420: SJU 2026-12-01 16:24:00 → ORD 2026-12-01 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
  • DM1003: SJU 2026-12-01 16:24:00 → PUJ 2026-12-01 17:25:00; layover at PUJ: 105 minutes.
  • DM5420: PUJ 2026-12-01 19:10:00 → ORD 2026-12-01 22:20:00.
• DM DM5481 / DM1002: ORD 2026-12-05 05:45:00 → SJU 2026-12-05 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
  • DM5481: ORD 2026-12-05 05:45:00 → PUJ 2026-12-05 12:30:00; layover at PUJ: 88 minutes.
  • DM1002: PUJ 2026-12-05 13:58:00 → SJU 2026-12-05 15:03:00.

2026-12-01 → 2026-12-05 · Axel-exclusive $400.00

• Delta Air Lines DL1780 / DL2804: SJU 2026-12-01 14:55:00 → ORD 2026-12-01 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
  • DL1780: SJU 2026-12-01 14:55:00 → BOS 2026-12-01 18:11:00; layover at BOS: 149 minutes.
  • DL2804: BOS 2026-12-01 20:40:00 → ORD 2026-12-01 22:36:00.
• Delta Air Lines DL5666 / DL1961: ORD 2026-12-05 06:00:00 → SJU 2026-12-05 16:56:00; 1 stop(s) via JFK; 536 minutes. Local airport times.
  • DL5666: ORD 2026-12-05 06:00:00 → JFK 2026-12-05 09:20:00; layover at JFK: 170 minutes.
  • DL1961: JFK 2026-12-05 12:10:00 → SJU 2026-12-05 16:56:00.

2026-12-01 → 2026-12-05 · Axel-exclusive $410.00

• American Airlines AA2436: SJU 2026-12-01 05:00:00 → ORD 2026-12-01 08:39:00; nonstop; 339 minutes. Local airport times.
• American Airlines AA1555: ORD 2026-12-05 17:01:00 → SJU 2026-12-05 23:39:00; nonstop; 278 minutes. Local airport times.

2026-12-01 → 2026-12-05 · Axel-exclusive $420.00

• United Airlines UA2089: SJU 2026-12-01 08:25:00 → ORD 2026-12-01 11:49:00; nonstop; 324 minutes. Local airport times.
• United Airlines UA1996: ORD 2026-12-05 08:52:00 → SJU 2026-12-05 15:40:00; nonstop; 288 minutes. Local airport times.

2026-12-01 → 2026-12-05 · Axel-exclusive $240.00

• Frontier Airlines F92871 / F91441: SJU 2026-12-01 05:19:00 → ORD 2026-12-01 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
  • F92871: SJU 2026-12-01 05:19:00 → ATL 2026-12-01 08:26:00; layover at ATL: 131 minutes.
  • F91441: ATL 2026-12-01 10:37:00 → ORD 2026-12-01 12:00:00.
• Frontier Airlines F93346: ORD 2026-12-05 23:53:00 → SJU 2026-12-06 06:32:00; nonstop; 279 minutes. Local airport times.

2026-12-01 → 2026-12-05 · Axel-exclusive $240.00

• Frontier Airlines F91015 / F92113: SJU 2026-12-01 07:28:00 → ORD 2026-12-01 14:12:00; 1 stop(s) via PHL; 524 minutes. Local airport times.
  • F91015: SJU 2026-12-01 07:28:00 → PHL 2026-12-01 10:36:00; layover at PHL: 123 minutes.
  • F92113: PHL 2026-12-01 12:39:00 → ORD 2026-12-01 14:12:00.
• Frontier Airlines F93346: ORD 2026-12-05 23:53:00 → SJU 2026-12-06 06:32:00; nonstop; 279 minutes. Local airport times.

2026-12-01 → 2026-12-05 · Axel-exclusive $392.50

• American Airlines AA508 / AA595: SJU 2026-12-01 08:30:00 → ORD 2026-12-01 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
  • AA508: SJU 2026-12-01 08:30:00 → PHL 2026-12-01 11:39:00; layover at PHL: 135 minutes.
  • AA595: PHL 2026-12-01 13:54:00 → ORD 2026-12-01 15:34:00.
• American Airlines AA1555: ORD 2026-12-05 17:01:00 → SJU 2026-12-05 23:39:00; nonstop; 278 minutes. Local airport times.

2026-12-01 → 2026-12-05 · Axel-exclusive $402.50

• United Airlines UA2022 / UA2331: SJU 2026-12-01 08:05:00 → ORD 2026-12-01 14:38:00; 1 stop(s) via IAD; 513 minutes. Local airport times.
  • UA2022: SJU 2026-12-01 08:05:00 → IAD 2026-12-01 11:09:00; layover at IAD: 126 minutes.
  • UA2331: IAD 2026-12-01 13:15:00 → ORD 2026-12-01 14:38:00.
• United Airlines UA1996: ORD 2026-12-05 08:52:00 → SJU 2026-12-05 15:40:00; nonstop; 288 minutes. Local airport times.

Explore this route

• All dates for this route
• Nov 30, 2026 · Return options
• Dec 2, 2026 · Return options
• Hotels in Chicago with Axel

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