San Juan (SJU) to Chicago (ORD) · Dec 27, 2026 · one way

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

2026-12-27 · one way · Axel-exclusive $182.00

• Frontier Airlines F94789: SJU 2026-12-27 22:26:00 → ORD 2026-12-28 01:33:00; nonstop; 307 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $301.00

• American Airlines AA2213: SJU 2026-12-27 15:50:00 → ORD 2026-12-27 19:29:00; nonstop; 339 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $308.00

• United Airlines UA2089: SJU 2026-12-27 08:25:00 → ORD 2026-12-27 11:49:00; nonstop; 324 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $231.00

• DM DM1003 / DM5420: SJU 2026-12-27 16:24:00 → ORD 2026-12-27 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
  • DM1003: SJU 2026-12-27 16:24:00 → PUJ 2026-12-27 17:25:00; layover at PUJ: 105 minutes.
  • DM5420: PUJ 2026-12-27 19:10:00 → ORD 2026-12-27 22:20:00.

2026-12-27 · one way · Axel-exclusive $294.00

• Delta Air Lines DL1780 / DL2804: SJU 2026-12-27 14:55:00 → ORD 2026-12-27 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
  • DL1780: SJU 2026-12-27 14:55:00 → BOS 2026-12-27 18:11:00; layover at BOS: 149 minutes.
  • DL2804: BOS 2026-12-27 20:40:00 → ORD 2026-12-27 22:36:00.

2026-12-27 · one way · Axel-exclusive $301.00

• American Airlines AA2436: SJU 2026-12-27 05:00:00 → ORD 2026-12-27 08:39:00; nonstop; 339 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $308.00

• United Airlines UA2088: SJU 2026-12-27 16:55:00 → ORD 2026-12-27 20:26:00; nonstop; 331 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $168.00

• Frontier Airlines F92871 / F91441: SJU 2026-12-27 05:19:00 → ORD 2026-12-27 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
  • F92871: SJU 2026-12-27 05:19:00 → ATL 2026-12-27 08:26:00; layover at ATL: 131 minutes.
  • F91441: ATL 2026-12-27 10:37:00 → ORD 2026-12-27 12:00:00.

2026-12-27 · one way · Axel-exclusive $168.00

• Frontier Airlines F91015 / F92113: SJU 2026-12-27 07:28:00 → ORD 2026-12-27 14:12:00; 1 stop(s) via PHL; 524 minutes. Local airport times.
  • F91015: SJU 2026-12-27 07:28:00 → PHL 2026-12-27 10:36:00; layover at PHL: 123 minutes.
  • F92113: PHL 2026-12-27 12:39:00 → ORD 2026-12-27 14:12:00.

2026-12-27 · one way · Axel-exclusive $273.00

• American Airlines AA508 / AA595: SJU 2026-12-27 08:30:00 → ORD 2026-12-27 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
  • AA508: SJU 2026-12-27 08:30:00 → PHL 2026-12-27 11:39:00; layover at PHL: 135 minutes.
  • AA595: PHL 2026-12-27 13:54:00 → ORD 2026-12-27 15:34:00.

2026-12-27 · one way · Axel-exclusive $280.00

• United Airlines UA2022 / UA2331: SJU 2026-12-27 08:05:00 → ORD 2026-12-27 14:38:00; 1 stop(s) via IAD; 513 minutes. Local airport times.
  • UA2022: SJU 2026-12-27 08:05:00 → IAD 2026-12-27 11:09:00; layover at IAD: 126 minutes.
  • UA2331: IAD 2026-12-27 13:15:00 → ORD 2026-12-27 14:38:00.

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
• Dec 26, 2026 · Return options
• Dec 28, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

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