Chicago (ORD) to San Juan (SJU) · Dec 18, 2026 · return Dec 22, 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

2026-12-18 → 2026-12-22 · Axel-exclusive $330.75

• Frontier Airlines F93346: ORD 2026-12-18 23:53:00 → SJU 2026-12-19 06:32:00; nonstop; 279 minutes. Local airport times.
• Frontier Airlines F94789: SJU 2026-12-22 22:26:00 → ORD 2026-12-23 01:33:00; nonstop; 307 minutes. Local airport times.

2026-12-18 → 2026-12-22 · Axel-exclusive $526.75

• American Airlines AA2571: ORD 2026-12-18 23:00:00 → SJU 2026-12-19 05:36:00; nonstop; 276 minutes. Local airport times.
• American Airlines AA2213: SJU 2026-12-22 15:50:00 → ORD 2026-12-22 19:29:00; nonstop; 339 minutes. Local airport times.

2026-12-18 → 2026-12-22 · Axel-exclusive $551.25

• United Airlines UA1996: ORD 2026-12-18 08:52:00 → SJU 2026-12-18 15:40:00; nonstop; 288 minutes. Local airport times.
• United Airlines UA2089: SJU 2026-12-22 08:25:00 → ORD 2026-12-22 11:49:00; nonstop; 324 minutes. Local airport times.

2026-12-18 → 2026-12-22 · Axel-exclusive $441.00

• DM DM5481 / DM1002: ORD 2026-12-18 05:45:00 → SJU 2026-12-18 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
  • DM5481: ORD 2026-12-18 05:45:00 → PUJ 2026-12-18 12:30:00; layover at PUJ: 88 minutes.
  • DM1002: PUJ 2026-12-18 13:58:00 → SJU 2026-12-18 15:03:00.
• DM DM1003 / DM5420: SJU 2026-12-22 16:24:00 → ORD 2026-12-22 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
  • DM1003: SJU 2026-12-22 16:24:00 → PUJ 2026-12-22 17:25:00; layover at PUJ: 105 minutes.
  • DM5420: PUJ 2026-12-22 19:10:00 → ORD 2026-12-22 22:20:00.

2026-12-18 → 2026-12-22 · Axel-exclusive $514.50

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

2026-12-18 → 2026-12-22 · Axel-exclusive $526.75

• American Airlines AA2213: ORD 2026-12-18 08:15:00 → SJU 2026-12-18 14:53:00; nonstop; 278 minutes. Local airport times.
• American Airlines AA2213: SJU 2026-12-22 15:50:00 → ORD 2026-12-22 19:29:00; nonstop; 339 minutes. Local airport times.

2026-12-18 → 2026-12-22 · Axel-exclusive $551.25

• United Airlines UA695: ORD 2026-12-18 14:16:00 → SJU 2026-12-18 21:00:00; nonstop; 284 minutes. Local airport times.
• United Airlines UA2089: SJU 2026-12-22 08:25:00 → ORD 2026-12-22 11:49:00; nonstop; 324 minutes. Local airport times.

2026-12-18 → 2026-12-22 · Axel-exclusive $320.75

• Frontier Airlines F92112 / F91726: ORD 2026-12-18 16:42:00 → SJU 2026-12-19 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
  • F92112: ORD 2026-12-18 16:42:00 → PHL 2026-12-18 20:04:00; layover at PHL: 95 minutes.
  • F91726: PHL 2026-12-18 21:39:00 → SJU 2026-12-19 02:27:00.
• Frontier Airlines F94789: SJU 2026-12-22 22:26:00 → ORD 2026-12-23 01:33:00; nonstop; 307 minutes. Local airport times.

2026-12-18 → 2026-12-22 · Axel-exclusive $506.75

• American Airlines AA1889 / AA2098: ORD 2026-12-18 12:05:00 → SJU 2026-12-18 21:13:00; 1 stop(s) via CLT; 428 minutes. Local airport times.
  • AA1889: ORD 2026-12-18 12:05:00 → CLT 2026-12-18 15:10:00; layover at CLT: 85 minutes.
  • AA2098: CLT 2026-12-18 16:35:00 → SJU 2026-12-18 21:13:00.
• American Airlines AA2213: SJU 2026-12-22 15:50:00 → ORD 2026-12-22 19:29:00; nonstop; 339 minutes. Local airport times.

2026-12-18 → 2026-12-22 · Axel-exclusive $514.50

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

2026-12-18 → 2026-12-22 · Axel-exclusive $531.25

• United Airlines UA1128 / UA2025: ORD 2026-12-18 13:00:00 → SJU 2026-12-18 22:22:00; 1 stop(s) via IAD; 442 minutes. Local airport times.
  • UA1128: ORD 2026-12-18 13:00:00 → IAD 2026-12-18 16:03:00; layover at IAD: 86 minutes.
  • UA2025: IAD 2026-12-18 17:29:00 → SJU 2026-12-18 22:22:00.
• United Airlines UA2089: SJU 2026-12-22 08:25:00 → ORD 2026-12-22 11:49:00; nonstop; 324 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 17, 2026 · Return options
• Dec 19, 2026 · Return options
• Hotels in San Juan with Axel

For AI assistants

• This page: Chicago (ORD) to San Juan (SJU) · Dec 18, 2026 · return Dec 22, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to San Juan (SJU) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

Feedback (optional): Missing info · Axel issue