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

Chicago (ORD) to San Juan (SJU), Jan 11, 2027: round trips from $250, one way from $130

Chicago (ORD) to San Juan (SJU), Jan 11, 2027: round trips from $250, one way from $130 on Axel, checked Oct 29, 2026. Lowest published fares: $250 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Jan 11–13, 2027; $130 one way, Axel-exclusive, Frontier Airlines, 1 stop, Jan 11, 2027; 1 adult, economy, checked Oct 29, 2026.

ORD → SJU1 adulteconomyOne way and round trips

30 flight options · 3 airlines

Choose your return date

One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

January 2027

Flights for your trip

  1. Mon, Jan 11 · One way

    Frontier Airlines
    4:42 pmORD
    7h 45m
    PHL · 1h 35m
    2:27 am+1SJU

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  2. Mon, Jan 11 · One way

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

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  3. Mon, Jan 11 – Tue, Jan 12

    Frontier Airlines
    4:42 pmORD
    7h 45m
    PHL · 1h 35m
    2:27 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.

  4. Mon, Jan 11 – Tue, Jan 12

    American Airlines
    11:00 pmORD
    4h 36m
    Nonstop
    5:36 am+1SJU
    American Airlines
    3:50 pmSJU
    5h 39m
    Nonstop
    7:29 pmORD

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  5. Mon, Jan 11 – Wed, Jan 13

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  6. Mon, Jan 11 – Wed, Jan 13

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  7. Mon, Jan 11 – Thu, Jan 14

    Frontier Airlines
    4:42 pmORD
    7h 45m
    PHL · 1h 35m
    2:27 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.

  8. Mon, Jan 11 – Thu, Jan 14

    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.

  9. Mon, Jan 11 – Fri, Jan 15

    Frontier Airlines
    4:42 pmORD
    7h 45m
    PHL · 1h 35m
    2:27 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.

  10. Mon, Jan 11 – Fri, Jan 15

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  11. Mon, Jan 11 – Sun, Jan 17

    Frontier Airlines
    4:42 pmORD
    7h 45m
    PHL · 1h 35m
    2:27 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.

  12. Mon, Jan 11 – Sun, Jan 17

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  13. Mon, Jan 11 – Mon, Jan 18

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  14. Mon, Jan 11 – Mon, Jan 18

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  15. Mon, Jan 11 – Tue, Jan 19

    Frontier Airlines
    4:42 pmORD
    7h 45m
    PHL · 1h 35m
    2:27 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.

  16. Mon, Jan 11 – Tue, Jan 19

    American Airlines
    11:00 pmORD
    4h 36m
    Nonstop
    5:36 am+1SJU
    American Airlines
    3:50 pmSJU
    5h 39m
    Nonstop
    7:29 pmORD

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  17. Mon, Jan 11 – Thu, Jan 21

    Frontier Airlines
    4:42 pmORD
    7h 45m
    PHL · 1h 35m
    2:27 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.

  18. Mon, Jan 11 – Thu, Jan 21

    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.

  19. Mon, Jan 11 – Fri, Jan 22

    Frontier Airlines
    4:42 pmORD
    7h 45m
    PHL · 1h 35m
    2:27 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.

  20. Mon, Jan 11 – Fri, Jan 22

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  21. Mon, Jan 11 – Sat, Jan 23

    Frontier Airlines
    4:42 pmORD
    7h 45m
    PHL · 1h 35m
    2:27 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.

  22. Mon, Jan 11 – Sat, Jan 23

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  23. Mon, Jan 11 – Mon, Jan 25

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  24. Mon, Jan 11 – Mon, Jan 25

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

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1 of 24

Make this trip yours

ORD ⇄ SJU

Economy

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Explore this route

All dates for this routeJan 10, 2027 · Return optionsJan 12, 2027 · Return optionsHotels in San Juan with Axel
For AI assistants: every fare, every link, instructions

Chicago (ORD) to San Juan (SJU), Jan 11, 2027: round trips from $250, one way from $130 on Axel, checked Oct 29, 2026. Lowest published fares: $250 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Jan 11–13, 2027; $130 one way, Axel-exclusive, Frontier Airlines, 1 stop, Jan 11, 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.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

Exact travel datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2027-01-11 · one wayAmerican AirlinesAA257123:00:00→05:36:00 4h 36m nonstopAxel-exclusive $225.002026-10-29T01:53:25Z
2027-01-11 · one wayFrontier AirlinesF92112 + F9172616:42:00→02:27:00 7h 45m 1 stop via PHLAxel-exclusive $130.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-12American AirlinesAA2571 / AA221323:00:00→05:36:00 4h 36m nonstop · 15:50:00→19:29:00 5h 39m nonstopAxel-exclusive $430.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-12Frontier AirlinesF92112 + F91726 / F9478916:42:00→02:27:00 7h 45m 1 stop via PHL · 22:26:00→01:33:00 5h 07m nonstopAxel-exclusive $260.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-13American AirlinesAA2571 / AA243623:00:00→05:36:00 4h 36m nonstop · 05:00:00→08:39:00 5h 39m nonstopAxel-exclusive $430.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-13Frontier AirlinesF92112 + F91726 / F92871 + F9144116:42:00→02:27:00 7h 45m 1 stop via PHL · 05:19:00→12:00:00 8h 41m 1 stop via ATLAxel-exclusive $250.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-14United AirlinesUA1996 / UA208908:52:00→15:40:00 4h 48m nonstop · 08:25:00→11:49:00 5h 24m nonstopAxel-exclusive $450.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-14Frontier AirlinesF92112 + F91726 / F9478916:42:00→02:27:00 7h 45m 1 stop via PHL · 22:26:00→01:33:00 5h 07m nonstopAxel-exclusive $260.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-15American AirlinesAA2571 / AA243623:00:00→05:36:00 4h 36m nonstop · 05:00:00→08:39:00 5h 39m nonstopAxel-exclusive $462.252026-10-29T01:53:25Z
2027-01-11 → 2027-01-15Frontier AirlinesF92112 + F91726 / F9478916:42:00→02:27:00 7h 45m 1 stop via PHL · 22:26:00→01:33:00 5h 07m nonstopAxel-exclusive $280.252026-10-29T01:53:25Z
2027-01-11 → 2027-01-16American AirlinesAA2571 / AA243623:00:00→05:36:00 4h 36m nonstop · 05:00:00→08:39:00 5h 39m nonstopAxel-exclusive $462.252026-10-29T01:53:25Z
2027-01-11 → 2027-01-16Frontier AirlinesF92112 + F91726 / F9478916:42:00→02:27:00 7h 45m 1 stop via PHL · 22:26:00→01:33:00 5h 07m nonstopAxel-exclusive $280.252026-10-29T01:53:25Z
2027-01-11 → 2027-01-17American AirlinesAA2571 / AA243623:00:00→05:36:00 4h 36m nonstop · 05:00:00→08:39:00 5h 39m nonstopAxel-exclusive $462.252026-10-29T01:53:25Z
2027-01-11 → 2027-01-17Frontier AirlinesF92112 + F91726 / F9478916:42:00→02:27:00 7h 45m 1 stop via PHL · 22:26:00→01:33:00 5h 07m nonstopAxel-exclusive $280.252026-10-29T01:53:25Z
2027-01-11 → 2027-01-18American AirlinesAA2571 / AA243623:00:00→05:36:00 4h 36m nonstop · 05:00:00→08:39:00 5h 39m nonstopAxel-exclusive $462.252026-10-29T01:53:25Z
2027-01-11 → 2027-01-18Frontier AirlinesF92112 + F91726 / F9334516:42:00→02:27:00 7h 45m 1 stop via PHL · 19:12:00→22:21:00 5h 09m nonstopAxel-exclusive $280.252026-10-29T01:53:25Z
2027-01-11 → 2027-01-19American AirlinesAA2571 / AA221323:00:00→05:36:00 4h 36m nonstop · 15:50:00→19:29:00 5h 39m nonstopAxel-exclusive $430.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-19Frontier AirlinesF92112 + F91726 / F9478916:42:00→02:27:00 7h 45m 1 stop via PHL · 22:26:00→01:33:00 5h 07m nonstopAxel-exclusive $260.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-20American AirlinesAA2571 / AA243623:00:00→05:36:00 4h 36m nonstop · 05:00:00→08:39:00 5h 39m nonstopAxel-exclusive $430.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-20Frontier AirlinesF92112 + F91726 / F92871 + F9144116:42:00→02:27:00 7h 45m 1 stop via PHL · 05:19:00→12:00:00 8h 41m 1 stop via ATLAxel-exclusive $250.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-21United AirlinesUA1996 / UA208908:52:00→15:40:00 4h 48m nonstop · 08:25:00→11:49:00 5h 24m nonstopAxel-exclusive $450.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-21Frontier AirlinesF92112 + F91726 / F9478916:42:00→02:27:00 7h 45m 1 stop via PHL · 22:26:00→01:33:00 5h 07m nonstopAxel-exclusive $260.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-22American AirlinesAA2571 / AA243623:00:00→05:36:00 4h 36m nonstop · 05:00:00→08:39:00 5h 39m nonstopAxel-exclusive $430.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-22Frontier AirlinesF92112 + F91726 / F9478916:42:00→02:27:00 7h 45m 1 stop via PHL · 22:26:00→01:33:00 5h 07m nonstopAxel-exclusive $260.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-23American AirlinesAA2571 / AA243623:00:00→05:36:00 4h 36m nonstop · 05:00:00→08:39:00 5h 39m nonstopAxel-exclusive $430.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-23Frontier AirlinesF92112 + F91726 / F9478916:42:00→02:27:00 7h 45m 1 stop via PHL · 22:26:00→01:33:00 5h 07m nonstopAxel-exclusive $260.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-24American AirlinesAA2571 / AA243623:00:00→05:36:00 4h 36m nonstop · 05:00:00→08:39:00 5h 39m nonstopAxel-exclusive $430.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-24Frontier AirlinesF92112 + F91726 / F9478916:42:00→02:27:00 7h 45m 1 stop via PHL · 22:26:00→01:33:00 5h 07m nonstopAxel-exclusive $260.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-25American AirlinesAA2571 / AA243623:00:00→05:36:00 4h 36m nonstop · 05:00:00→08:39:00 5h 39m nonstopAxel-exclusive $430.002026-10-29T01:53:25Z
2027-01-11 → 2027-01-25Frontier AirlinesF92112 + F91726 / F9334516:42:00→02:27:00 7h 45m 1 stop via PHL · 19:12:00→22:21:00 5h 09m nonstopAxel-exclusive $260.002026-10-29T01:53:25Z

Hotels in San Juan for these trips

Hotels: under a trip, hotels in San Juan for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

All hotels in San Juan

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

2027-01-11 · one way · Axel-exclusive $130.00

  • Frontier Airlines F92112 / F91726: ORD 2027-01-11 16:42:00 → SJU 2027-01-12 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-11 16:42:00 → PHL 2027-01-11 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-11 21:39:00 → SJU 2027-01-12 02:27:00.

2027-01-11 · one way · Axel-exclusive $225.00

  • American Airlines AA2571: ORD 2027-01-11 23:00:00 → SJU 2027-01-12 05:36:00; nonstop; 276 minutes. Local airport times.

2027-01-11 → 2027-01-12 · Axel-exclusive $260.00

  • Frontier Airlines F92112 / F91726: ORD 2027-01-11 16:42:00 → SJU 2027-01-12 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-11 16:42:00 → PHL 2027-01-11 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-11 21:39:00 → SJU 2027-01-12 02:27:00.
  • Frontier Airlines F94789: SJU 2027-01-12 22:26:00 → ORD 2027-01-13 01:33:00; nonstop; 307 minutes. Local airport times.

2027-01-11 → 2027-01-12 · Axel-exclusive $430.00

  • American Airlines AA2571: ORD 2027-01-11 23:00:00 → SJU 2027-01-12 05:36:00; nonstop; 276 minutes. Local airport times.
  • American Airlines AA2213: SJU 2027-01-12 15:50:00 → ORD 2027-01-12 19:29:00; nonstop; 339 minutes. Local airport times.

2027-01-11 → 2027-01-13 · Axel-exclusive $250.00

  • Frontier Airlines F92112 / F91726: ORD 2027-01-11 16:42:00 → SJU 2027-01-12 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-11 16:42:00 → PHL 2027-01-11 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-11 21:39:00 → SJU 2027-01-12 02:27:00.
  • Frontier Airlines F92871 / F91441: SJU 2027-01-13 05:19:00 → ORD 2027-01-13 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
    • F92871: SJU 2027-01-13 05:19:00 → ATL 2027-01-13 08:26:00; layover at ATL: 131 minutes.
    • F91441: ATL 2027-01-13 10:37:00 → ORD 2027-01-13 12:00:00.

2027-01-11 → 2027-01-13 · Axel-exclusive $430.00

  • American Airlines AA2571: ORD 2027-01-11 23:00:00 → SJU 2027-01-12 05:36:00; nonstop; 276 minutes. Local airport times.
  • American Airlines AA2436: SJU 2027-01-13 05:00:00 → ORD 2027-01-13 08:39:00; nonstop; 339 minutes. Local airport times.

2027-01-11 → 2027-01-14 · Axel-exclusive $260.00

  • Frontier Airlines F92112 / F91726: ORD 2027-01-11 16:42:00 → SJU 2027-01-12 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-11 16:42:00 → PHL 2027-01-11 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-11 21:39:00 → SJU 2027-01-12 02:27:00.
  • Frontier Airlines F94789: SJU 2027-01-14 22:26:00 → ORD 2027-01-15 01:33:00; nonstop; 307 minutes. Local airport times.

2027-01-11 → 2027-01-14 · Axel-exclusive $450.00

  • United Airlines UA1996: ORD 2027-01-11 08:52:00 → SJU 2027-01-11 15:40:00; nonstop; 288 minutes. Local airport times.
  • United Airlines UA2089: SJU 2027-01-14 08:25:00 → ORD 2027-01-14 11:49:00; nonstop; 324 minutes. Local airport times.

2027-01-11 → 2027-01-15 · Axel-exclusive $280.25

  • Frontier Airlines F92112 / F91726: ORD 2027-01-11 16:42:00 → SJU 2027-01-12 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-11 16:42:00 → PHL 2027-01-11 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-11 21:39:00 → SJU 2027-01-12 02:27:00.
  • Frontier Airlines F94789: SJU 2027-01-15 22:26:00 → ORD 2027-01-16 01:33:00; nonstop; 307 minutes. Local airport times.

2027-01-11 → 2027-01-15 · Axel-exclusive $462.25

  • American Airlines AA2571: ORD 2027-01-11 23:00:00 → SJU 2027-01-12 05:36:00; nonstop; 276 minutes. Local airport times.
  • American Airlines AA2436: SJU 2027-01-15 05:00:00 → ORD 2027-01-15 08:39:00; nonstop; 339 minutes. Local airport times.

2027-01-11 → 2027-01-17 · Axel-exclusive $280.25

  • Frontier Airlines F92112 / F91726: ORD 2027-01-11 16:42:00 → SJU 2027-01-12 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-11 16:42:00 → PHL 2027-01-11 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-11 21:39:00 → SJU 2027-01-12 02:27:00.
  • Frontier Airlines F94789: SJU 2027-01-17 22:26:00 → ORD 2027-01-18 01:33:00; nonstop; 307 minutes. Local airport times.

2027-01-11 → 2027-01-17 · Axel-exclusive $462.25

  • American Airlines AA2571: ORD 2027-01-11 23:00:00 → SJU 2027-01-12 05:36:00; nonstop; 276 minutes. Local airport times.
  • American Airlines AA2436: SJU 2027-01-17 05:00:00 → ORD 2027-01-17 08:39:00; nonstop; 339 minutes. Local airport times.

2027-01-11 → 2027-01-18 · Axel-exclusive $280.25

  • Frontier Airlines F92112 / F91726: ORD 2027-01-11 16:42:00 → SJU 2027-01-12 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-11 16:42:00 → PHL 2027-01-11 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-11 21:39:00 → SJU 2027-01-12 02:27:00.
  • Frontier Airlines F93345: SJU 2027-01-18 19:12:00 → ORD 2027-01-18 22:21:00; nonstop; 309 minutes. Local airport times.

2027-01-11 → 2027-01-18 · Axel-exclusive $462.25

  • American Airlines AA2571: ORD 2027-01-11 23:00:00 → SJU 2027-01-12 05:36:00; nonstop; 276 minutes. Local airport times.
  • American Airlines AA2436: SJU 2027-01-18 05:00:00 → ORD 2027-01-18 08:39:00; nonstop; 339 minutes. Local airport times.

2027-01-11 → 2027-01-19 · Axel-exclusive $260.00

  • Frontier Airlines F92112 / F91726: ORD 2027-01-11 16:42:00 → SJU 2027-01-12 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-11 16:42:00 → PHL 2027-01-11 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-11 21:39:00 → SJU 2027-01-12 02:27:00.
  • Frontier Airlines F94789: SJU 2027-01-19 22:26:00 → ORD 2027-01-20 01:33:00; nonstop; 307 minutes. Local airport times.

2027-01-11 → 2027-01-19 · Axel-exclusive $430.00

  • American Airlines AA2571: ORD 2027-01-11 23:00:00 → SJU 2027-01-12 05:36:00; nonstop; 276 minutes. Local airport times.
  • American Airlines AA2213: SJU 2027-01-19 15:50:00 → ORD 2027-01-19 19:29:00; nonstop; 339 minutes. Local airport times.

2027-01-11 → 2027-01-21 · Axel-exclusive $260.00

  • Frontier Airlines F92112 / F91726: ORD 2027-01-11 16:42:00 → SJU 2027-01-12 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-11 16:42:00 → PHL 2027-01-11 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-11 21:39:00 → SJU 2027-01-12 02:27:00.
  • Frontier Airlines F94789: SJU 2027-01-21 22:26:00 → ORD 2027-01-22 01:33:00; nonstop; 307 minutes. Local airport times.

2027-01-11 → 2027-01-21 · Axel-exclusive $450.00

  • United Airlines UA1996: ORD 2027-01-11 08:52:00 → SJU 2027-01-11 15:40:00; nonstop; 288 minutes. Local airport times.
  • United Airlines UA2089: SJU 2027-01-21 08:25:00 → ORD 2027-01-21 11:49:00; nonstop; 324 minutes. Local airport times.

2027-01-11 → 2027-01-22 · Axel-exclusive $260.00

  • Frontier Airlines F92112 / F91726: ORD 2027-01-11 16:42:00 → SJU 2027-01-12 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-11 16:42:00 → PHL 2027-01-11 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-11 21:39:00 → SJU 2027-01-12 02:27:00.
  • Frontier Airlines F94789: SJU 2027-01-22 22:26:00 → ORD 2027-01-23 01:33:00; nonstop; 307 minutes. Local airport times.

2027-01-11 → 2027-01-22 · Axel-exclusive $430.00

  • American Airlines AA2571: ORD 2027-01-11 23:00:00 → SJU 2027-01-12 05:36:00; nonstop; 276 minutes. Local airport times.
  • American Airlines AA2436: SJU 2027-01-22 05:00:00 → ORD 2027-01-22 08:39:00; nonstop; 339 minutes. Local airport times.

2027-01-11 → 2027-01-23 · Axel-exclusive $260.00

  • Frontier Airlines F92112 / F91726: ORD 2027-01-11 16:42:00 → SJU 2027-01-12 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-11 16:42:00 → PHL 2027-01-11 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-11 21:39:00 → SJU 2027-01-12 02:27:00.
  • Frontier Airlines F94789: SJU 2027-01-23 22:26:00 → ORD 2027-01-24 01:33:00; nonstop; 307 minutes. Local airport times.

2027-01-11 → 2027-01-23 · Axel-exclusive $430.00

  • American Airlines AA2571: ORD 2027-01-11 23:00:00 → SJU 2027-01-12 05:36:00; nonstop; 276 minutes. Local airport times.
  • American Airlines AA2436: SJU 2027-01-23 05:00:00 → ORD 2027-01-23 08:39:00; nonstop; 339 minutes. Local airport times.

2027-01-11 → 2027-01-25 · Axel-exclusive $260.00

  • Frontier Airlines F92112 / F91726: ORD 2027-01-11 16:42:00 → SJU 2027-01-12 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2027-01-11 16:42:00 → PHL 2027-01-11 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2027-01-11 21:39:00 → SJU 2027-01-12 02:27:00.
  • Frontier Airlines F93345: SJU 2027-01-25 19:12:00 → ORD 2027-01-25 22:21:00; nonstop; 309 minutes. Local airport times.

2027-01-11 → 2027-01-25 · Axel-exclusive $430.00

  • American Airlines AA2571: ORD 2027-01-11 23:00:00 → SJU 2027-01-12 05:36:00; nonstop; 276 minutes. Local airport times.
  • American Airlines AA2436: SJU 2027-01-25 05:00:00 → ORD 2027-01-25 08:39:00; nonstop; 339 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Chicago (ORD) to San Juan (SJU) · Jan 11, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in San Juan for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
  • Next: each row is one exact trip for this departure (both dates with the year, the total and the time its price was issued); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
  • 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.