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

San Juan (SJU) to Chicago (ORD), Nov 19, 2026: round trips from $240, one way from $130

San Juan (SJU) to Chicago (ORD), Nov 19, 2026: round trips from $240, one way from $130 on Axel, checked Oct 29, 2026. Lowest published fares: $240 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 19–30, 2026; $130 one way, Axel-exclusive, Frontier Airlines, nonstop, Nov 19, 2026; 1 adult, economy, checked Oct 29, 2026.

SJU → ORD1 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.

November 2026

Flights for your trip

  1. Thu, Nov 19 · One way

    Frontier Airlines
    7:12 pmSJU
    5h 9m
    Nonstop
    10:21 pmORD

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  2. Thu, Nov 19 · One way

    DM
    4:24 pmSJU
    7h 56m
    PUJ · 1h 45m
    10:20 pmORD

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  3. Thu, Nov 19 – Fri, Nov 20

    Frontier Airlines
    7:12 pmSJU
    5h 9m
    Nonstop
    10:21 pmORD
    Frontier Airlines
    11:53 pmORD
    4h 39m
    Nonstop
    6:32 am+1SJU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  4. Thu, Nov 19 – Fri, Nov 20

    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

    Availability is checked when you select these flights.

  5. Thu, Nov 19 – Sat, Nov 21

    Frontier Airlines
    7:12 pmSJU
    5h 9m
    Nonstop
    10:21 pmORD
    Frontier Airlines
    11:53 pmORD
    4h 39m
    Nonstop
    6:32 am+1SJU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  6. Thu, Nov 19 – Sat, Nov 21

    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

    Availability is checked when you select these flights.

  7. Thu, Nov 19 – Sun, Nov 22

    Frontier Airlines
    7:12 pmSJU
    5h 9m
    Nonstop
    10:21 pmORD
    Frontier Airlines
    11:53 pmORD
    4h 39m
    Nonstop
    6:32 am+1SJU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  8. Thu, Nov 19 – Sun, Nov 22

    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

    Availability is checked when you select these flights.

  9. Thu, Nov 19 – Mon, Nov 23

    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

    Availability is checked when you select these flights.

  10. Thu, Nov 19 – Mon, Nov 23

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  11. Thu, Nov 19 – Wed, Nov 25

    Frontier Airlines
    7:12 pmSJU
    5h 9m
    Nonstop
    10:21 pmORD
    Frontier Airlines
    11:53 pmORD
    4h 39m
    Nonstop
    6:32 am+1SJU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  12. Thu, Nov 19 – Wed, Nov 25

    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

    Availability is checked when you select these flights.

  13. Thu, Nov 19 – Thu, Nov 26

    Frontier Airlines
    7:12 pmSJU
    5h 9m
    Nonstop
    10:21 pmORD
    Frontier Airlines
    11:53 pmORD
    4h 39m
    Nonstop
    6:32 am+1SJU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  14. Thu, Nov 19 – Thu, Nov 26

    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

    Availability is checked when you select these flights.

  15. Thu, Nov 19 – Fri, Nov 27

    Frontier Airlines
    7:12 pmSJU
    5h 9m
    Nonstop
    10:21 pmORD
    Frontier Airlines
    11:53 pmORD
    4h 39m
    Nonstop
    6:32 am+1SJU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  16. Thu, Nov 19 – Fri, Nov 27

    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

    Availability is checked when you select these flights.

  17. Thu, Nov 19 – Sun, Nov 29

    Frontier Airlines
    7:12 pmSJU
    5h 9m
    Nonstop
    10:21 pmORD
    Frontier Airlines
    11:53 pmORD
    4h 39m
    Nonstop
    6:32 am+1SJU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  18. Thu, Nov 19 – Sun, Nov 29

    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

    Availability is checked when you select these flights.

  19. Thu, Nov 19 – Mon, Nov 30

    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

    Availability is checked when you select these flights.

  20. Thu, Nov 19 – Mon, Nov 30

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  21. Thu, Nov 19 – Tue, Dec 1

    Frontier Airlines
    7:12 pmSJU
    5h 9m
    Nonstop
    10:21 pmORD
    Frontier Airlines
    11:53 pmORD
    4h 39m
    Nonstop
    6:32 am+1SJU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  22. Thu, Nov 19 – Tue, Dec 1

    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

    Availability is checked when you select these flights.

  23. Thu, Nov 19 – Thu, Dec 3

    Frontier Airlines
    7:12 pmSJU
    5h 9m
    Nonstop
    10:21 pmORD
    Frontier Airlines
    11:53 pmORD
    4h 39m
    Nonstop
    6:32 am+1SJU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  24. Thu, Nov 19 – Thu, Dec 3

    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

    Availability is checked when you select these flights.

Swipe to see 23 more recent deals.

1 of 24

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 routeNov 18, 2026 · Return optionsNov 20, 2026 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

San Juan (SJU) to Chicago (ORD), Nov 19, 2026: round trips from $240, one way from $130 on Axel, checked Oct 29, 2026. Lowest published fares: $240 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 19–30, 2026; $130 one way, Axel-exclusive, Frontier Airlines, nonstop, Nov 19, 2026; 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)
2026-11-19 · one wayFrontier AirlinesF9334519:12:00→22:21:00 5h 09m nonstopAxel-exclusive $130.002026-10-29T01:23:44Z
2026-11-19 · one wayDMDM1003 + DM542016:24:00→22:20:00 7h 56m 1 stop via PUJAxel-exclusive $165.002026-10-29T01:23:44Z
2026-11-19 → 2026-11-20Frontier AirlinesF93345 / F9334619:12:00→22:21:00 5h 09m nonstop · 23:53:00→06:32:00 4h 39m nonstopAxel-exclusive $250.002026-10-29T01:23:44Z
2026-11-19 → 2026-11-20DMDM1003 + DM5420 / DM5481 + DM100216:24:00→22:20:00 7h 56m 1 stop via PUJ · 05:45:00→15:03:00 7h 18m 1 stop via PUJAxel-exclusive $320.002026-10-29T01:23:44Z
2026-11-19 → 2026-11-21Frontier AirlinesF93345 / F9334619:12:00→22:21:00 5h 09m nonstop · 23:53:00→06:32:00 4h 39m nonstopAxel-exclusive $281.252026-10-29T01:23:44Z
2026-11-19 → 2026-11-21DMDM1003 + DM5420 / DM5481 + DM100216:24:00→22:20:00 7h 56m 1 stop via PUJ · 05:45:00→15:03:00 7h 18m 1 stop via PUJAxel-exclusive $360.002026-10-29T01:23:44Z
2026-11-19 → 2026-11-22Frontier AirlinesF93345 / F9334619:12:00→22:21:00 5h 09m nonstop · 23:53:00→06:32:00 4h 39m nonstopAxel-exclusive $281.252026-10-29T01:23:44Z
2026-11-19 → 2026-11-22DMDM1003 + DM5420 / DM5481 + DM100216:24:00→22:20:00 7h 56m 1 stop via PUJ · 05:45:00→15:03:00 7h 18m 1 stop via PUJAxel-exclusive $360.002026-10-29T01:23:44Z
2026-11-19 → 2026-11-23United AirlinesUA2089 / UA199608:25:00→11:49:00 5h 24m nonstop · 08:52:00→15:40:00 4h 48m nonstopAxel-exclusive $472.502026-10-29T01:23:44Z
2026-11-19 → 2026-11-23Frontier AirlinesF93345 / F92112 + F9172619:12:00→22:21:00 5h 09m nonstop · 16:42:00→02:27:00 7h 45m 1 stop via PHLAxel-exclusive $268.752026-10-29T01:23:44Z
2026-11-19 → 2026-11-24Frontier AirlinesF93345 / F9334619:12:00→22:21:00 5h 09m nonstop · 23:53:00→06:32:00 4h 39m nonstopAxel-exclusive $281.252026-10-29T01:23:44Z
2026-11-19 → 2026-11-24DMDM1003 + DM5420 / DM5481 + DM100216:24:00→22:20:00 7h 56m 1 stop via PUJ · 05:45:00→15:03:00 7h 18m 1 stop via PUJAxel-exclusive $360.002026-10-29T01:23:44Z
2026-11-19 → 2026-11-25Frontier AirlinesF93345 / F9334619:12:00→22:21:00 5h 09m nonstop · 23:53:00→06:32:00 4h 39m nonstopAxel-exclusive $281.252026-10-29T01:23:44Z
2026-11-19 → 2026-11-25DMDM1003 + DM5420 / DM5481 + DM100216:24:00→22:20:00 7h 56m 1 stop via PUJ · 05:45:00→15:03:00 7h 18m 1 stop via PUJAxel-exclusive $360.002026-10-29T01:23:44Z
2026-11-19 → 2026-11-26Frontier AirlinesF93345 / F9334619:12:00→22:21:00 5h 09m nonstop · 23:53:00→06:32:00 4h 39m nonstopAxel-exclusive $281.252026-10-29T01:23:44Z
2026-11-19 → 2026-11-26DMDM1003 + DM5420 / DM5481 + DM100216:24:00→22:20:00 7h 56m 1 stop via PUJ · 05:45:00→15:03:00 7h 18m 1 stop via PUJAxel-exclusive $360.002026-10-29T01:23:44Z
2026-11-19 → 2026-11-27Frontier AirlinesF93345 / F9334619:12:00→22:21:00 5h 09m nonstop · 23:53:00→06:32:00 4h 39m nonstopAxel-exclusive $281.252026-10-29T01:23:44Z
2026-11-19 → 2026-11-27DMDM1003 + DM5420 / DM5481 + DM100216:24:00→22:20:00 7h 56m 1 stop via PUJ · 05:45:00→15:03:00 7h 18m 1 stop via PUJAxel-exclusive $360.002026-10-29T01:23:44Z
2026-11-19 → 2026-11-28Frontier AirlinesF93345 / F9334619:12:00→22:21:00 5h 09m nonstop · 23:53:00→06:32:00 4h 39m nonstopAxel-exclusive $281.252026-10-29T01:23:44Z
2026-11-19 → 2026-11-28DMDM1003 + DM5420 / DM5481 + DM100216:24:00→22:20:00 7h 56m 1 stop via PUJ · 05:45:00→15:03:00 7h 18m 1 stop via PUJAxel-exclusive $360.002026-10-29T01:23:44Z
2026-11-19 → 2026-11-29Frontier AirlinesF93345 / F9334619:12:00→22:21:00 5h 09m nonstop · 23:53:00→06:32:00 4h 39m nonstopAxel-exclusive $281.252026-10-29T01:23:44Z
2026-11-19 → 2026-11-29DMDM1003 + DM5420 / DM5481 + DM100216:24:00→22:20:00 7h 56m 1 stop via PUJ · 05:45:00→15:03:00 7h 18m 1 stop via PUJAxel-exclusive $360.002026-10-29T01:23:44Z
2026-11-19 → 2026-11-30United AirlinesUA2089 / UA199608:25:00→11:49:00 5h 24m nonstop · 08:52:00→15:40:00 4h 48m nonstopAxel-exclusive $420.002026-10-29T01:23:44Z
2026-11-19 → 2026-11-30Frontier AirlinesF93345 / F92112 + F9172619:12:00→22:21:00 5h 09m nonstop · 16:42:00→02:27:00 7h 45m 1 stop via PHLAxel-exclusive $240.002026-10-29T01:23:44Z
2026-11-19 → 2026-12-01Frontier AirlinesF93345 / F9334619:12:00→22:21:00 5h 09m nonstop · 23:53:00→06:32:00 4h 39m nonstopAxel-exclusive $250.002026-10-29T01:23:44Z
2026-11-19 → 2026-12-01DMDM1003 + DM5420 / DM5481 + DM100216:24:00→22:20:00 7h 56m 1 stop via PUJ · 05:45:00→15:03:00 7h 18m 1 stop via PUJAxel-exclusive $320.002026-10-29T01:23:44Z
2026-11-19 → 2026-12-02Frontier AirlinesF93345 / F9334619:12:00→22:21:00 5h 09m nonstop · 23:53:00→06:32:00 4h 39m nonstopAxel-exclusive $250.002026-10-29T01:23:44Z
2026-11-19 → 2026-12-02DMDM1003 + DM5420 / DM5481 + DM100216:24:00→22:20:00 7h 56m 1 stop via PUJ · 05:45:00→15:03:00 7h 18m 1 stop via PUJAxel-exclusive $320.002026-10-29T01:23:44Z
2026-11-19 → 2026-12-03Frontier AirlinesF93345 / F9334619:12:00→22:21:00 5h 09m nonstop · 23:53:00→06:32:00 4h 39m nonstopAxel-exclusive $250.002026-10-29T01:23:44Z
2026-11-19 → 2026-12-03DMDM1003 + DM5420 / DM5481 + DM100216:24:00→22:20:00 7h 56m 1 stop via PUJ · 05:45:00→15:03:00 7h 18m 1 stop via PUJAxel-exclusive $320.002026-10-29T01:23:44Z

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago 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 Chicago

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

2026-11-19 · one way · Axel-exclusive $130.00

  • Frontier Airlines F93345: SJU 2026-11-19 19:12:00 → ORD 2026-11-19 22:21:00; nonstop; 309 minutes. Local airport times.

2026-11-19 · one way · Axel-exclusive $165.00

  • DM DM1003 / DM5420: SJU 2026-11-19 16:24:00 → ORD 2026-11-19 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-11-19 16:24:00 → PUJ 2026-11-19 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-11-19 19:10:00 → ORD 2026-11-19 22:20:00.

2026-11-19 → 2026-11-20 · Axel-exclusive $250.00

  • Frontier Airlines F93345: SJU 2026-11-19 19:12:00 → ORD 2026-11-19 22:21:00; nonstop; 309 minutes. Local airport times.
  • Frontier Airlines F93346: ORD 2026-11-20 23:53:00 → SJU 2026-11-21 06:32:00; nonstop; 279 minutes. Local airport times.

2026-11-19 → 2026-11-20 · Axel-exclusive $320.00

  • DM DM1003 / DM5420: SJU 2026-11-19 16:24:00 → ORD 2026-11-19 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-11-19 16:24:00 → PUJ 2026-11-19 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-11-19 19:10:00 → ORD 2026-11-19 22:20:00.
  • DM DM5481 / DM1002: ORD 2026-11-20 05:45:00 → SJU 2026-11-20 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
    • DM5481: ORD 2026-11-20 05:45:00 → PUJ 2026-11-20 12:30:00; layover at PUJ: 88 minutes.
    • DM1002: PUJ 2026-11-20 13:58:00 → SJU 2026-11-20 15:03:00.

2026-11-19 → 2026-11-21 · Axel-exclusive $281.25

  • Frontier Airlines F93345: SJU 2026-11-19 19:12:00 → ORD 2026-11-19 22:21:00; nonstop; 309 minutes. Local airport times.
  • Frontier Airlines F93346: ORD 2026-11-21 23:53:00 → SJU 2026-11-22 06:32:00; nonstop; 279 minutes. Local airport times.

2026-11-19 → 2026-11-21 · Axel-exclusive $360.00

  • DM DM1003 / DM5420: SJU 2026-11-19 16:24:00 → ORD 2026-11-19 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-11-19 16:24:00 → PUJ 2026-11-19 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-11-19 19:10:00 → ORD 2026-11-19 22:20:00.
  • DM DM5481 / DM1002: ORD 2026-11-21 05:45:00 → SJU 2026-11-21 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
    • DM5481: ORD 2026-11-21 05:45:00 → PUJ 2026-11-21 12:30:00; layover at PUJ: 88 minutes.
    • DM1002: PUJ 2026-11-21 13:58:00 → SJU 2026-11-21 15:03:00.

2026-11-19 → 2026-11-22 · Axel-exclusive $281.25

  • Frontier Airlines F93345: SJU 2026-11-19 19:12:00 → ORD 2026-11-19 22:21:00; nonstop; 309 minutes. Local airport times.
  • Frontier Airlines F93346: ORD 2026-11-22 23:53:00 → SJU 2026-11-23 06:32:00; nonstop; 279 minutes. Local airport times.

2026-11-19 → 2026-11-22 · Axel-exclusive $360.00

  • DM DM1003 / DM5420: SJU 2026-11-19 16:24:00 → ORD 2026-11-19 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-11-19 16:24:00 → PUJ 2026-11-19 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-11-19 19:10:00 → ORD 2026-11-19 22:20:00.
  • DM DM5481 / DM1002: ORD 2026-11-22 05:45:00 → SJU 2026-11-22 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
    • DM5481: ORD 2026-11-22 05:45:00 → PUJ 2026-11-22 12:30:00; layover at PUJ: 88 minutes.
    • DM1002: PUJ 2026-11-22 13:58:00 → SJU 2026-11-22 15:03:00.

2026-11-19 → 2026-11-23 · Axel-exclusive $268.75

  • Frontier Airlines F93345: SJU 2026-11-19 19:12:00 → ORD 2026-11-19 22:21:00; nonstop; 309 minutes. Local airport times.
  • Frontier Airlines F92112 / F91726: ORD 2026-11-23 16:42:00 → SJU 2026-11-24 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2026-11-23 16:42:00 → PHL 2026-11-23 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2026-11-23 21:39:00 → SJU 2026-11-24 02:27:00.

2026-11-19 → 2026-11-23 · Axel-exclusive $472.50

  • United Airlines UA2089: SJU 2026-11-19 08:25:00 → ORD 2026-11-19 11:49:00; nonstop; 324 minutes. Local airport times.
  • United Airlines UA1996: ORD 2026-11-23 08:52:00 → SJU 2026-11-23 15:40:00; nonstop; 288 minutes. Local airport times.

2026-11-19 → 2026-11-25 · Axel-exclusive $281.25

  • Frontier Airlines F93345: SJU 2026-11-19 19:12:00 → ORD 2026-11-19 22:21:00; nonstop; 309 minutes. Local airport times.
  • Frontier Airlines F93346: ORD 2026-11-25 23:53:00 → SJU 2026-11-26 06:32:00; nonstop; 279 minutes. Local airport times.

2026-11-19 → 2026-11-25 · Axel-exclusive $360.00

  • DM DM1003 / DM5420: SJU 2026-11-19 16:24:00 → ORD 2026-11-19 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-11-19 16:24:00 → PUJ 2026-11-19 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-11-19 19:10:00 → ORD 2026-11-19 22:20:00.
  • DM DM5481 / DM1002: ORD 2026-11-25 05:45:00 → SJU 2026-11-25 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
    • DM5481: ORD 2026-11-25 05:45:00 → PUJ 2026-11-25 12:30:00; layover at PUJ: 88 minutes.
    • DM1002: PUJ 2026-11-25 13:58:00 → SJU 2026-11-25 15:03:00.

2026-11-19 → 2026-11-26 · Axel-exclusive $281.25

  • Frontier Airlines F93345: SJU 2026-11-19 19:12:00 → ORD 2026-11-19 22:21:00; nonstop; 309 minutes. Local airport times.
  • Frontier Airlines F93346: ORD 2026-11-26 23:53:00 → SJU 2026-11-27 06:32:00; nonstop; 279 minutes. Local airport times.

2026-11-19 → 2026-11-26 · Axel-exclusive $360.00

  • DM DM1003 / DM5420: SJU 2026-11-19 16:24:00 → ORD 2026-11-19 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-11-19 16:24:00 → PUJ 2026-11-19 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-11-19 19:10:00 → ORD 2026-11-19 22:20:00.
  • DM DM5481 / DM1002: ORD 2026-11-26 05:45:00 → SJU 2026-11-26 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
    • DM5481: ORD 2026-11-26 05:45:00 → PUJ 2026-11-26 12:30:00; layover at PUJ: 88 minutes.
    • DM1002: PUJ 2026-11-26 13:58:00 → SJU 2026-11-26 15:03:00.

2026-11-19 → 2026-11-27 · Axel-exclusive $281.25

  • Frontier Airlines F93345: SJU 2026-11-19 19:12:00 → ORD 2026-11-19 22:21:00; nonstop; 309 minutes. Local airport times.
  • Frontier Airlines F93346: ORD 2026-11-27 23:53:00 → SJU 2026-11-28 06:32:00; nonstop; 279 minutes. Local airport times.

2026-11-19 → 2026-11-27 · Axel-exclusive $360.00

  • DM DM1003 / DM5420: SJU 2026-11-19 16:24:00 → ORD 2026-11-19 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-11-19 16:24:00 → PUJ 2026-11-19 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-11-19 19:10:00 → ORD 2026-11-19 22:20:00.
  • DM DM5481 / DM1002: ORD 2026-11-27 05:45:00 → SJU 2026-11-27 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
    • DM5481: ORD 2026-11-27 05:45:00 → PUJ 2026-11-27 12:30:00; layover at PUJ: 88 minutes.
    • DM1002: PUJ 2026-11-27 13:58:00 → SJU 2026-11-27 15:03:00.

2026-11-19 → 2026-11-29 · Axel-exclusive $281.25

  • Frontier Airlines F93345: SJU 2026-11-19 19:12:00 → ORD 2026-11-19 22:21:00; nonstop; 309 minutes. Local airport times.
  • Frontier Airlines F93346: ORD 2026-11-29 23:53:00 → SJU 2026-11-30 06:32:00; nonstop; 279 minutes. Local airport times.

2026-11-19 → 2026-11-29 · Axel-exclusive $360.00

  • DM DM1003 / DM5420: SJU 2026-11-19 16:24:00 → ORD 2026-11-19 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-11-19 16:24:00 → PUJ 2026-11-19 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-11-19 19:10:00 → ORD 2026-11-19 22:20:00.
  • DM DM5481 / DM1002: ORD 2026-11-29 05:45:00 → SJU 2026-11-29 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
    • DM5481: ORD 2026-11-29 05:45:00 → PUJ 2026-11-29 12:30:00; layover at PUJ: 88 minutes.
    • DM1002: PUJ 2026-11-29 13:58:00 → SJU 2026-11-29 15:03:00.

2026-11-19 → 2026-11-30 · Axel-exclusive $240.00

  • Frontier Airlines F93345: SJU 2026-11-19 19:12:00 → ORD 2026-11-19 22:21:00; nonstop; 309 minutes. Local airport times.
  • Frontier Airlines F92112 / F91726: ORD 2026-11-30 16:42:00 → SJU 2026-12-01 02:27:00; 1 stop(s) via PHL; 465 minutes. Local airport times.
    • F92112: ORD 2026-11-30 16:42:00 → PHL 2026-11-30 20:04:00; layover at PHL: 95 minutes.
    • F91726: PHL 2026-11-30 21:39:00 → SJU 2026-12-01 02:27:00.

2026-11-19 → 2026-11-30 · Axel-exclusive $420.00

  • United Airlines UA2089: SJU 2026-11-19 08:25:00 → ORD 2026-11-19 11:49:00; nonstop; 324 minutes. Local airport times.
  • United Airlines UA1996: ORD 2026-11-30 08:52:00 → SJU 2026-11-30 15:40:00; nonstop; 288 minutes. Local airport times.

2026-11-19 → 2026-12-01 · Axel-exclusive $250.00

  • Frontier Airlines F93345: SJU 2026-11-19 19:12:00 → ORD 2026-11-19 22:21:00; nonstop; 309 minutes. Local airport times.
  • Frontier Airlines F93346: ORD 2026-12-01 23:53:00 → SJU 2026-12-02 06:32:00; nonstop; 279 minutes. Local airport times.

2026-11-19 → 2026-12-01 · Axel-exclusive $320.00

  • DM DM1003 / DM5420: SJU 2026-11-19 16:24:00 → ORD 2026-11-19 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-11-19 16:24:00 → PUJ 2026-11-19 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-11-19 19:10:00 → ORD 2026-11-19 22:20:00.
  • DM DM5481 / DM1002: ORD 2026-12-01 05:45:00 → SJU 2026-12-01 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
    • DM5481: ORD 2026-12-01 05:45:00 → PUJ 2026-12-01 12:30:00; layover at PUJ: 88 minutes.
    • DM1002: PUJ 2026-12-01 13:58:00 → SJU 2026-12-01 15:03:00.

2026-11-19 → 2026-12-03 · Axel-exclusive $250.00

  • Frontier Airlines F93345: SJU 2026-11-19 19:12:00 → ORD 2026-11-19 22:21:00; nonstop; 309 minutes. Local airport times.
  • Frontier Airlines F93346: ORD 2026-12-03 23:53:00 → SJU 2026-12-04 06:32:00; nonstop; 279 minutes. Local airport times.

2026-11-19 → 2026-12-03 · Axel-exclusive $320.00

  • DM DM1003 / DM5420: SJU 2026-11-19 16:24:00 → ORD 2026-11-19 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
    • DM1003: SJU 2026-11-19 16:24:00 → PUJ 2026-11-19 17:25:00; layover at PUJ: 105 minutes.
    • DM5420: PUJ 2026-11-19 19:10:00 → ORD 2026-11-19 22:20:00.
  • DM DM5481 / DM1002: ORD 2026-12-03 05:45:00 → SJU 2026-12-03 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
    • DM5481: ORD 2026-12-03 05:45:00 → PUJ 2026-12-03 12:30:00; layover at PUJ: 88 minutes.
    • DM1002: PUJ 2026-12-03 13:58:00 → SJU 2026-12-03 15:03:00.

Explore this route

For AI assistants

  • This page: San Juan (SJU) to Chicago (ORD) · Nov 19, 2026 · 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 Chicago 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 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. 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.