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Route overview: Chicago to San Juan (SJU) flight deals

Chicago → San Juan

Dec 13, 2026 · return Dec 17, 2026

ORD → SJU1 adulteconomyRound trip

9 flight options · 5 airlines

Nonstop flights

Sun, Dec 13 – Thu, Dec 17

Frontier Airlines
11:53 pmORD
4h 39m
Nonstop
6:32 am+1SJU
Frontier Airlines
10:26 pmSJU
5h 7m
Nonstop
1:33 am+1ORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Thu, Dec 17

United Airlines
8:52 amORD
4h 48m
Nonstop
3:40 pmSJU
United Airlines
8:25 amSJU
5h 24m
Nonstop
11:49 amORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Thu, Dec 17

United Airlines
2:16 pmORD
4h 44m
Nonstop
9:00 pmSJU
United Airlines
8:25 amSJU
5h 24m
Nonstop
11:49 amORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Sun, Dec 13 – Thu, Dec 17

DM
5:45 amORD
7h 18m
PUJ · 1h 28m
3:03 pmSJU
DM
4:24 pmSJU
7h 56m
PUJ · 1h 45m
10:20 pmORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Thu, Dec 17

American Airlines
12:05 pmORD
7h 8m
CLT · 1h 25m
9:13 pmSJU
American Airlines
8:30 amSJU
9h 4m
PHL · 2h 15m
3:34 pmORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Thu, Dec 17

Delta Air Lines
8:04 amORD
7h 42m
ATL · 2h 21m
5:46 pmSJU
Delta Air Lines
2:55 pmSJU
9h 41m
BOS · 2h 29m
10:36 pmORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Thu, Dec 17

American Airlines
8:05 amORD
4h 43m
Nonstop
2:48 pmSJU
American Airlines
8:30 amSJU
9h 4m
PHL · 2h 15m
3:34 pmORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Thu, Dec 17

Delta Air Lines
6:00 amORD
8h 56m
JFK · 2h 50m
4:56 pmSJU
Delta Air Lines
2:55 pmSJU
9h 41m
BOS · 2h 29m
10:36 pmORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 13 – Thu, Dec 17

United Airlines
1:00 pmORD
7h 22m
IAD · 1h 26m
10:22 pmSJU
United Airlines
8:25 amSJU
5h 24m
Nonstop
11:49 amORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Make this trip yours

ORD ⇄ SJU

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Explore this route

All dates for this routeDec 12, 2026 · Return optionsDec 14, 2026 · Return optionsHotels in San Juan with Axel
For AI assistants: every fare, every link, instructions

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.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-13 → 2026-12-17Frontier AirlinesF93346 / F94789Axel-exclusive $270.002026-10-29T01:53:25Z
2026-12-13 → 2026-12-17United AirlinesUA1996 / UA2089Axel-exclusive $450.002026-10-29T01:53:25Z
2026-12-13 → 2026-12-17DMDM5481 + DM1002 / DM1003 + DM5420Axel-exclusive $360.002026-10-29T01:53:25Z
2026-12-13 → 2026-12-17American AirlinesAA1889 + AA2098 / AA508 + AA595Axel-exclusive $390.002026-10-29T01:53:25Z
2026-12-13 → 2026-12-17Delta Air LinesDL1687 + DL1946 / DL1780 + DL2804Axel-exclusive $420.002026-10-29T01:53:25Z
2026-12-13 → 2026-12-17United AirlinesUA695 / UA2089Axel-exclusive $450.002026-10-29T01:53:25Z
2026-12-13 → 2026-12-17American AirlinesAA3096 / AA508 + AA595Axel-exclusive $410.002026-10-29T01:53:25Z
2026-12-13 → 2026-12-17Delta Air LinesDL5666 + DL1961 / DL1780 + DL2804Axel-exclusive $420.002026-10-29T01:53:25Z
2026-12-13 → 2026-12-17United AirlinesUA1128 + UA2025 / UA2089Axel-exclusive $430.002026-10-29T01:53:25Z

Route overview: Chicago to San Juan (SJU) flight deals

2026-12-13 → 2026-12-17 · Axel-exclusive $270.00

  • Frontier Airlines F93346: ORD 2026-12-13 23:53:00 → SJU 2026-12-14 06:32:00; nonstop; 279 minutes. Local airport times.
  • Frontier Airlines F94789: SJU 2026-12-17 22:26:00 → ORD 2026-12-18 01:33:00; nonstop; 307 minutes. Local airport times.

2026-12-13 → 2026-12-17 · Axel-exclusive $450.00

  • United Airlines UA1996: ORD 2026-12-13 08:52:00 → SJU 2026-12-13 15:40:00; nonstop; 288 minutes. Local airport times.
  • United Airlines UA2089: SJU 2026-12-17 08:25:00 → ORD 2026-12-17 11:49:00; nonstop; 324 minutes. Local airport times.

2026-12-13 → 2026-12-17 · Axel-exclusive $360.00

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

2026-12-13 → 2026-12-17 · Axel-exclusive $390.00

  • American Airlines AA1889 / AA2098: ORD 2026-12-13 12:05:00 → SJU 2026-12-13 21:13:00; 1 stop(s) via CLT; 428 minutes. Local airport times.
    • AA1889: ORD 2026-12-13 12:05:00 → CLT 2026-12-13 15:10:00; layover at CLT: 85 minutes.
    • AA2098: CLT 2026-12-13 16:35:00 → SJU 2026-12-13 21:13:00.
  • American Airlines AA508 / AA595: SJU 2026-12-17 08:30:00 → ORD 2026-12-17 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
    • AA508: SJU 2026-12-17 08:30:00 → PHL 2026-12-17 11:39:00; layover at PHL: 135 minutes.
    • AA595: PHL 2026-12-17 13:54:00 → ORD 2026-12-17 15:34:00.

2026-12-13 → 2026-12-17 · Axel-exclusive $420.00

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

2026-12-13 → 2026-12-17 · Axel-exclusive $450.00

  • United Airlines UA695: ORD 2026-12-13 14:16:00 → SJU 2026-12-13 21:00:00; nonstop; 284 minutes. Local airport times.
  • United Airlines UA2089: SJU 2026-12-17 08:25:00 → ORD 2026-12-17 11:49:00; nonstop; 324 minutes. Local airport times.

2026-12-13 → 2026-12-17 · Axel-exclusive $410.00

  • American Airlines AA3096: ORD 2026-12-13 08:05:00 → SJU 2026-12-13 14:48:00; nonstop; 283 minutes. Local airport times.
  • American Airlines AA508 / AA595: SJU 2026-12-17 08:30:00 → ORD 2026-12-17 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
    • AA508: SJU 2026-12-17 08:30:00 → PHL 2026-12-17 11:39:00; layover at PHL: 135 minutes.
    • AA595: PHL 2026-12-17 13:54:00 → ORD 2026-12-17 15:34:00.

2026-12-13 → 2026-12-17 · Axel-exclusive $420.00

  • Delta Air Lines DL5666 / DL1961: ORD 2026-12-13 06:00:00 → SJU 2026-12-13 16:56:00; 1 stop(s) via JFK; 536 minutes. Local airport times.
    • DL5666: ORD 2026-12-13 06:00:00 → JFK 2026-12-13 09:20:00; layover at JFK: 170 minutes.
    • DL1961: JFK 2026-12-13 12:10:00 → SJU 2026-12-13 16:56:00.
  • Delta Air Lines DL1780 / DL2804: SJU 2026-12-17 14:55:00 → ORD 2026-12-17 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
    • DL1780: SJU 2026-12-17 14:55:00 → BOS 2026-12-17 18:11:00; layover at BOS: 149 minutes.
    • DL2804: BOS 2026-12-17 20:40:00 → ORD 2026-12-17 22:36:00.

2026-12-13 → 2026-12-17 · Axel-exclusive $430.00

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

Explore this route

For AI assistants

  • This page: Chicago (ORD) to San Juan (SJU) · Dec 13, 2026 · return Dec 17, 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.