San Juan (SJU) to Chicago (ORD), Jan 8–22, 2027: from $240 round trip

Lowest published fare: $240 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Jan 8–22, 2027, 1 adult, economy, checked Oct 29, 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

2027-01-08 → 2027-01-22 · Axel-exclusive $250.00

• Frontier Airlines F94789: SJU 2027-01-08 22:26:00 → ORD 2027-01-09 01:33:00; nonstop; 307 minutes. Local airport times.
• Frontier Airlines F93346: ORD 2027-01-22 23:53:00 → SJU 2027-01-23 06:32:00; nonstop; 279 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $410.00

• American Airlines AA2436: SJU 2027-01-08 05:00:00 → ORD 2027-01-08 08:39:00; nonstop; 339 minutes. Local airport times.
• American Airlines AA1555: ORD 2027-01-22 17:01:00 → SJU 2027-01-22 23:39:00; nonstop; 278 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $420.00

• United Airlines UA2088: SJU 2027-01-08 16:55:00 → ORD 2027-01-08 20:26:00; nonstop; 331 minutes. Local airport times.
• United Airlines UA1996: ORD 2027-01-22 08:52:00 → SJU 2027-01-22 15:40:00; nonstop; 288 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $320.00

• DM DM1003 / DM5420: SJU 2027-01-08 16:24:00 → ORD 2027-01-08 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
  • DM1003: SJU 2027-01-08 16:24:00 → PUJ 2027-01-08 17:25:00; layover at PUJ: 105 minutes.
  • DM5420: PUJ 2027-01-08 19:10:00 → ORD 2027-01-08 22:20:00.
• DM DM5481 / DM1002: ORD 2027-01-22 05:45:00 → SJU 2027-01-22 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
  • DM5481: ORD 2027-01-22 05:45:00 → PUJ 2027-01-22 12:30:00; layover at PUJ: 88 minutes.
  • DM1002: PUJ 2027-01-22 13:58:00 → SJU 2027-01-22 15:03:00.

2027-01-08 → 2027-01-22 · Axel-exclusive $400.00

• Delta Air Lines DL1780 / DL2804: SJU 2027-01-08 14:55:00 → ORD 2027-01-08 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
  • DL1780: SJU 2027-01-08 14:55:00 → BOS 2027-01-08 18:11:00; layover at BOS: 149 minutes.
  • DL2804: BOS 2027-01-08 20:40:00 → ORD 2027-01-08 22:36:00.
• Delta Air Lines DL5666 / DL1961: ORD 2027-01-22 06:00:00 → SJU 2027-01-22 16:56:00; 1 stop(s) via JFK; 536 minutes. Local airport times.
  • DL5666: ORD 2027-01-22 06:00:00 → JFK 2027-01-22 09:20:00; layover at JFK: 170 minutes.
  • DL1961: JFK 2027-01-22 12:10:00 → SJU 2027-01-22 16:56:00.

2027-01-08 → 2027-01-22 · Axel-exclusive $410.00

• American Airlines AA2213: SJU 2027-01-08 15:50:00 → ORD 2027-01-08 19:29:00; nonstop; 339 minutes. Local airport times.
• American Airlines AA1555: ORD 2027-01-22 17:01:00 → SJU 2027-01-22 23:39:00; nonstop; 278 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $420.00

• United Airlines UA2089: SJU 2027-01-08 08:25:00 → ORD 2027-01-08 11:49:00; nonstop; 324 minutes. Local airport times.
• United Airlines UA1996: ORD 2027-01-22 08:52:00 → SJU 2027-01-22 15:40:00; nonstop; 288 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $240.00

• Frontier Airlines F91015 / F92113: SJU 2027-01-08 07:28:00 → ORD 2027-01-08 14:12:00; 1 stop(s) via PHL; 524 minutes. Local airport times.
  • F91015: SJU 2027-01-08 07:28:00 → PHL 2027-01-08 10:36:00; layover at PHL: 123 minutes.
  • F92113: PHL 2027-01-08 12:39:00 → ORD 2027-01-08 14:12:00.
• Frontier Airlines F93346: ORD 2027-01-22 23:53:00 → SJU 2027-01-23 06:32:00; nonstop; 279 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $240.00

• Frontier Airlines F92871 / F91441: SJU 2027-01-08 05:19:00 → ORD 2027-01-08 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
  • F92871: SJU 2027-01-08 05:19:00 → ATL 2027-01-08 08:26:00; layover at ATL: 131 minutes.
  • F91441: ATL 2027-01-08 10:37:00 → ORD 2027-01-08 12:00:00.
• Frontier Airlines F93346: ORD 2027-01-22 23:53:00 → SJU 2027-01-23 06:32:00; nonstop; 279 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $392.50

• American Airlines AA508 / AA595: SJU 2027-01-08 08:30:00 → ORD 2027-01-08 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
  • AA508: SJU 2027-01-08 08:30:00 → PHL 2027-01-08 11:39:00; layover at PHL: 135 minutes.
  • AA595: PHL 2027-01-08 13:54:00 → ORD 2027-01-08 15:34:00.
• American Airlines AA1555: ORD 2027-01-22 17:01:00 → SJU 2027-01-22 23:39:00; nonstop; 278 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $402.50

• United Airlines UA2089: SJU 2027-01-08 08:25:00 → ORD 2027-01-08 11:47:00; nonstop; 322 minutes. Local airport times.
• United Airlines UA1128 / UA2025: ORD 2027-01-22 13:00:00 → SJU 2027-01-22 22:22:00; 1 stop(s) via IAD; 442 minutes. Local airport times.
  • UA1128: ORD 2027-01-22 13:00:00 → IAD 2027-01-22 16:03:00; layover at IAD: 86 minutes.
  • UA2025: IAD 2027-01-22 17:29:00 → SJU 2027-01-22 22:22:00.

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
• Jan 7, 2027 · Return options
• Jan 9, 2027 · Return options
• Hotels in Chicago with Axel

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