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

San Juan → Chicago

Dec 21, 2026 · return Jan 4, 2027

SJU → ORD1 adulteconomyRound trip

10 flight options · 4 airlines

Nonstop flights

Mon, Dec 21 – Mon, Jan 4

American Airlines
3:52 pmSJU
5h 38m
Nonstop
7:30 pmORD
American Airlines
11:00 pmORD
4h 36m
Nonstop
5:36 am+1SJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

United Airlines
4:55 pmSJU
5h 31m
Nonstop
8:26 pmORD
United Airlines
2:16 pmORD
4h 44m
Nonstop
9:00 pmSJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

American Airlines
5:00 amSJU
5h 39m
Nonstop
8:39 amORD
American Airlines
11:00 pmORD
4h 36m
Nonstop
5:36 am+1SJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

United Airlines
8:25 amSJU
5h 22m
Nonstop
11:47 amORD
United Airlines
2:16 pmORD
4h 44m
Nonstop
9:00 pmSJU

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Mon, Jan 4

Frontier Airlines
5:19 amSJU
8h 41m
ATL · 2h 11m
12:00 pmORD
Frontier Airlines
4:42 pmORD
7h 45m
PHL · 1h 35m
2:27 am+1SJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Frontier Airlines
7:28 amSJU
8h 44m
PHL · 2h 3m
2:12 pmORD
Frontier Airlines
4:42 pmORD
7h 45m
PHL · 1h 35m
2:27 am+1SJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Frontier Airlines
7:12 pmSJU
5h 9m
Nonstop
10:21 pmORD
Frontier Airlines
4:42 pmORD
7h 45m
PHL · 1h 35m
2:27 am+1SJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

American Airlines
8:30 amSJU
9h 4m
PHL · 2h 15m
3:34 pmORD
American Airlines
11:00 pmORD
4h 36m
Nonstop
5:36 am+1SJU

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

United Airlines
8:05 amSJU
8h 33m
IAD · 2h 6m
2:38 pmORD
United Airlines
2:16 pmORD
4h 44m
Nonstop
9:00 pmSJU

Round-trip total · 1 adult · Taxes included

Make this trip yours

SJU ⇄ ORD

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 20, 2026 → Jan 3, 2027Dec 22, 2026 → Jan 5, 2027
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.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

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

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-21 → 2027-01-04American AirlinesAA2279 / AA2571$563.752026-10-29T01:23:44Z
2026-12-21 → 2027-01-04United AirlinesUA2088 / UA695$577.502026-10-29T01:23:44Z
2026-12-21 → 2027-01-04Frontier AirlinesF92871 + F91441 / F92112 + F91726$316.252026-10-29T01:23:44Z
2026-12-21 → 2027-01-04DMDM1003 + DM5420 / DM5481 + DM1002$440.002026-10-29T01:23:44Z
2026-12-21 → 2027-01-04American AirlinesAA2436 / AA2571$563.752026-10-29T01:23:44Z
2026-12-21 → 2027-01-04United AirlinesUA2089 / UA695$577.502026-10-29T01:23:44Z
2026-12-21 → 2027-01-04Frontier AirlinesF91015 + F92113 / F92112 + F91726$316.252026-10-29T01:23:44Z
2026-12-21 → 2027-01-04Frontier AirlinesF93345 / F92112 + F91726$330.252026-10-29T01:23:44Z
2026-12-21 → 2027-01-04American AirlinesAA508 + AA595 / AA2571$539.252026-10-29T01:23:44Z
2026-12-21 → 2027-01-04United AirlinesUA2022 + UA2331 / UA695$553.002026-10-29T01:23:44Z

2026-12-21 → 2027-01-04 · $563.75

  • American Airlines AA2279: SJU 2026-12-21 15:52:00 → ORD 2026-12-21 19:30:00; nonstop; 338 minutes. Local airport times.
  • American Airlines AA2571: ORD 2027-01-04 23:00:00 → SJU 2027-01-05 05:36:00; nonstop; 276 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $577.50

  • United Airlines UA2088: SJU 2026-12-21 16:55:00 → ORD 2026-12-21 20:26:00; nonstop; 331 minutes. Local airport times.
  • United Airlines UA695: ORD 2027-01-04 14:16:00 → SJU 2027-01-04 21:00:00; nonstop; 284 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $316.25

  • Frontier Airlines F92871 / F91441: SJU 2026-12-21 05:19:00 → ORD 2026-12-21 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
    • F92871: SJU 2026-12-21 05:19:00 → ATL 2026-12-21 08:26:00; layover at ATL: 131 minutes.
    • F91441: ATL 2026-12-21 10:37:00 → ORD 2026-12-21 12:00:00.
  • Frontier Airlines F92112 / F91726: ORD 2027-01-04 16:42:00 → SJU 2027-01-05 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-04 16:42:00 → PHL 2027-01-04 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-04 21:39:00 → SJU 2027-01-05 02:27:00.

2026-12-21 → 2027-01-04 · $440.00

  • DM DM1003 / DM5420: SJU 2026-12-21 16:24:00 → ORD 2026-12-21 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-12-21 16:24:00 → PUJ 2026-12-21 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-12-21 19:10:00 → ORD 2026-12-21 22:20:00.
  • DM DM5481 / DM1002: ORD 2027-01-04 05:45:00 → SJU 2027-01-04 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
    • DM5481: ORD 2027-01-04 05:45:00 → PUJ 2027-01-04 12:30:00; layover at PUJ: 88 minutes.
    • DM1002: PUJ 2027-01-04 13:58:00 → SJU 2027-01-04 15:03:00.

2026-12-21 → 2027-01-04 · $563.75

  • American Airlines AA2436: SJU 2026-12-21 05:00:00 → ORD 2026-12-21 08:39:00; nonstop; 339 minutes. Local airport times.
  • American Airlines AA2571: ORD 2027-01-04 23:00:00 → SJU 2027-01-05 05:36:00; nonstop; 276 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $577.50

  • United Airlines UA2089: SJU 2026-12-21 08:25:00 → ORD 2026-12-21 11:47:00; nonstop; 322 minutes. Local airport times.
  • United Airlines UA695: ORD 2027-01-04 14:16:00 → SJU 2027-01-04 21:00:00; nonstop; 284 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $316.25

  • Frontier Airlines F91015 / F92113: SJU 2026-12-21 07:28:00 → ORD 2026-12-21 14:12:00; 1 stop(s) via PHL; 524 minutes. Local airport times.
    • F91015: SJU 2026-12-21 07:28:00 → PHL 2026-12-21 10:36:00; layover at PHL: 123 minutes.
    • F92113: PHL 2026-12-21 12:39:00 → ORD 2026-12-21 14:12:00.
  • Frontier Airlines F92112 / F91726: ORD 2027-01-04 16:42:00 → SJU 2027-01-05 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-04 16:42:00 → PHL 2027-01-04 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-04 21:39:00 → SJU 2027-01-05 02:27:00.

2026-12-21 → 2027-01-04 · $330.25

  • Frontier Airlines F93345: SJU 2026-12-21 19:12:00 → ORD 2026-12-21 22:21:00; nonstop; 309 minutes. Local airport times.
  • Frontier Airlines F92112 / F91726: ORD 2027-01-04 16:42:00 → SJU 2027-01-05 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-04 16:42:00 → PHL 2027-01-04 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-04 21:39:00 → SJU 2027-01-05 02:27:00.

2026-12-21 → 2027-01-04 · $539.25

  • American Airlines AA508 / AA595: SJU 2026-12-21 08:30:00 → ORD 2026-12-21 15:34:00; 1 stop(s) via PHL; 544 minutes. Local airport times.
    • AA508: SJU 2026-12-21 08:30:00 → PHL 2026-12-21 11:39:00; layover at PHL: 135 minutes.
    • AA595: PHL 2026-12-21 13:54:00 → ORD 2026-12-21 15:34:00.
  • American Airlines AA2571: ORD 2027-01-04 23:00:00 → SJU 2027-01-05 05:36:00; nonstop; 276 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $553.00

  • United Airlines UA2022 / UA2331: SJU 2026-12-21 08:05:00 → ORD 2026-12-21 14:38:00; 1 stop(s) via IAD; 513 minutes. Local airport times.
    • UA2022: SJU 2026-12-21 08:05:00 → IAD 2026-12-21 11:09:00; layover at IAD: 126 minutes.
    • UA2331: IAD 2026-12-21 13:15:00 → ORD 2026-12-21 14:38:00.
  • United Airlines UA695: ORD 2027-01-04 14:16:00 → SJU 2027-01-04 21:00:00; nonstop; 284 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: San Juan (SJU) to Chicago (ORD) · Dec 21, 2026 · return Jan 4, 2027: 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.
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  • 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 San Juan to Chicago (ORD) 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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.