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

San Juan (SJU) to Chicago (MDW), Nov 26, 2026: round trips from $321, one way from $194

San Juan (SJU) to Chicago (MDW), Nov 26, 2026: round trips from $321, one way from $194 on Axel, checked Nov 12, 2026. Lowest published fares: $321 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 26–30, 2026; $194 one way, Axel-exclusive, Frontier Airlines, 1 stop, Nov 26, 2026; 1 adult, economy, checked Nov 12, 2026.

SJU → MDW1 adulteconomyOne way and round trips

30 flight options · 2 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 26 · One way

    Frontier Airlines
    5:01 amSJU
    8h 32m
    ATL · 2h 5m
    11:33 amMDW

    Example one-way total $194 · 1 adult · Taxes included

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  2. Thu, Nov 26 · One way

    Southwest Airlines
    6:05 amSJU
    8h 55m
    TPA · 2h 55m
    1:00 pmMDW

    Example one-way total $269 · 1 adult · Taxes included

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  3. Thu, Nov 26 – Fri, Nov 27

    Frontier Airlines
    5:01 amSJU
    8h 32m
    ATL · 2h 5m
    11:33 amMDW
    Frontier Airlines
    1:11 pmMDW
    8h 33m
    ATL · 2h 48m
    11:44 pmSJU

    Example round-trip total $356 · 1 adult · Taxes included

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  4. Thu, Nov 26 – Fri, Nov 27

    Southwest Airlines
    6:05 amSJU
    8h 55m
    TPA · 2h 55m
    1:00 pmMDW
    Southwest Airlines
    2:30 pmMDW
    8h 30m
    BWI · 2h 40m
    1:00 am+1SJU

    Example round-trip total $494 · 1 adult · Taxes included

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  5. Thu, Nov 26 – Sat, Nov 28

    Frontier Airlines
    5:01 amSJU
    8h 32m
    ATL · 2h 5m
    11:33 amMDW
    Frontier Airlines
    1:11 pmMDW
    8h 33m
    ATL · 2h 48m
    11:44 pmSJU

    Example round-trip total $356 · 1 adult · Taxes included

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  6. Thu, Nov 26 – Sat, Nov 28

    Southwest Airlines
    6:05 amSJU
    8h 55m
    TPA · 2h 55m
    1:00 pmMDW
    Southwest Airlines
    7:50 amMDW
    8h 35m
    STL · 2h 55m
    6:25 pmSJU

    Example round-trip total $494 · 1 adult · Taxes included

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  7. Thu, Nov 26 – Sun, Nov 29

    Frontier Airlines
    5:01 amSJU
    8h 32m
    ATL · 2h 5m
    11:33 amMDW
    Frontier Airlines
    1:11 pmMDW
    8h 33m
    ATL · 2h 48m
    11:44 pmSJU

    Example round-trip total $356 · 1 adult · Taxes included

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  8. Thu, Nov 26 – Sun, Nov 29

    Southwest Airlines
    6:05 amSJU
    8h 55m
    TPA · 2h 55m
    1:00 pmMDW
    Southwest Airlines
    2:30 pmMDW
    8h 30m
    BWI · 2h 40m
    1:00 am+1SJU

    Example round-trip total $494 · 1 adult · Taxes included

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  9. Thu, Nov 26 – Mon, Nov 30

    Frontier Airlines
    5:01 amSJU
    8h 32m
    ATL · 2h 5m
    11:33 amMDW
    Frontier Airlines
    1:11 pmMDW
    8h 33m
    ATL · 2h 48m
    11:44 pmSJU

    Example round-trip total $321 · 1 adult · Taxes included

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  10. Thu, Nov 26 – Mon, Nov 30

    Southwest Airlines
    6:05 amSJU
    8h 55m
    TPA · 2h 55m
    1:00 pmMDW
    Southwest Airlines
    2:30 pmMDW
    8h 30m
    BWI · 2h 40m
    1:00 am+1SJU

    Example round-trip total $444 · 1 adult · Taxes included

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  11. Thu, Nov 26 – Wed, Dec 2

    Frontier Airlines
    5:01 amSJU
    8h 32m
    ATL · 2h 5m
    11:33 amMDW
    Frontier Airlines
    1:11 pmMDW
    8h 33m
    ATL · 2h 48m
    11:44 pmSJU

    Example round-trip total $321 · 1 adult · Taxes included

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  12. Thu, Nov 26 – Wed, Dec 2

    Southwest Airlines
    6:05 amSJU
    8h 55m
    TPA · 2h 55m
    1:00 pmMDW
    Southwest Airlines
    1:20 pmMDW
    7h 5m
    TPA · 1h 20m
    10:25 pmSJU

    Example round-trip total $444 · 1 adult · Taxes included

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  13. Thu, Nov 26 – Thu, Dec 3

    Frontier Airlines
    5:01 amSJU
    8h 32m
    ATL · 2h 5m
    11:33 amMDW
    Frontier Airlines
    1:11 pmMDW
    8h 33m
    ATL · 2h 48m
    11:44 pmSJU

    Example round-trip total $321 · 1 adult · Taxes included

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  14. Thu, Nov 26 – Thu, Dec 3

    Southwest Airlines
    6:05 amSJU
    8h 55m
    TPA · 2h 55m
    1:00 pmMDW
    Southwest Airlines
    2:30 pmMDW
    8h 30m
    BWI · 2h 40m
    1:00 am+1SJU

    Example round-trip total $444 · 1 adult · Taxes included

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  15. Thu, Nov 26 – Fri, Dec 4

    Frontier Airlines
    5:01 amSJU
    8h 32m
    ATL · 2h 5m
    11:33 amMDW
    Frontier Airlines
    1:11 pmMDW
    8h 33m
    ATL · 2h 48m
    11:44 pmSJU

    Example round-trip total $321 · 1 adult · Taxes included

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  16. Thu, Nov 26 – Fri, Dec 4

    Southwest Airlines
    6:05 amSJU
    8h 55m
    TPA · 2h 55m
    1:00 pmMDW
    Southwest Airlines
    2:30 pmMDW
    8h 30m
    BWI · 2h 40m
    1:00 am+1SJU

    Example round-trip total $444 · 1 adult · Taxes included

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  17. Thu, Nov 26 – Sun, Dec 6

    Frontier Airlines
    5:01 amSJU
    8h 32m
    ATL · 2h 5m
    11:33 amMDW
    Frontier Airlines
    1:11 pmMDW
    8h 33m
    ATL · 2h 48m
    11:44 pmSJU

    Example round-trip total $321 · 1 adult · Taxes included

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  18. Thu, Nov 26 – Sun, Dec 6

    Southwest Airlines
    6:05 amSJU
    8h 55m
    TPA · 2h 55m
    1:00 pmMDW
    Southwest Airlines
    2:30 pmMDW
    8h 30m
    BWI · 2h 40m
    1:00 am+1SJU

    Example round-trip total $444 · 1 adult · Taxes included

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  19. Thu, Nov 26 – Mon, Dec 7

    Frontier Airlines
    5:01 amSJU
    8h 32m
    ATL · 2h 5m
    11:33 amMDW
    Frontier Airlines
    1:11 pmMDW
    8h 33m
    ATL · 2h 48m
    11:44 pmSJU

    Example round-trip total $321 · 1 adult · Taxes included

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  20. Thu, Nov 26 – Mon, Dec 7

    Southwest Airlines
    6:05 amSJU
    8h 55m
    TPA · 2h 55m
    1:00 pmMDW
    Southwest Airlines
    2:30 pmMDW
    8h 30m
    BWI · 2h 40m
    1:00 am+1SJU

    Example round-trip total $444 · 1 adult · Taxes included

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  21. Thu, Nov 26 – Tue, Dec 8

    Frontier Airlines
    5:01 amSJU
    8h 32m
    ATL · 2h 5m
    11:33 amMDW
    Frontier Airlines
    1:11 pmMDW
    8h 33m
    ATL · 2h 48m
    11:44 pmSJU

    Example round-trip total $321 · 1 adult · Taxes included

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  22. Thu, Nov 26 – Tue, Dec 8

    Southwest Airlines
    6:05 amSJU
    8h 55m
    TPA · 2h 55m
    1:00 pmMDW
    Southwest Airlines
    1:20 pmMDW
    7h 5m
    TPA · 1h 20m
    10:25 pmSJU

    Example round-trip total $444 · 1 adult · Taxes included

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  23. Thu, Nov 26 – Thu, Dec 10

    Frontier Airlines
    5:01 amSJU
    8h 32m
    ATL · 2h 5m
    11:33 amMDW
    Frontier Airlines
    1:11 pmMDW
    8h 33m
    ATL · 2h 48m
    11:44 pmSJU

    Example round-trip total $321 · 1 adult · Taxes included

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  24. Thu, Nov 26 – Thu, Dec 10

    Southwest Airlines
    6:05 amSJU
    8h 55m
    TPA · 2h 55m
    1:00 pmMDW
    Southwest Airlines
    7:50 amMDW
    8h 35m
    STL · 2h 55m
    6:25 pmSJU

    Example round-trip total $444 · 1 adult · Taxes included

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Make this trip yours

SJU ⇄ MDW

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 25, 2026 · Return optionsNov 27, 2026 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

San Juan (SJU) to Chicago (MDW), Nov 26, 2026: round trips from $321, one way from $194 on Axel, checked Nov 12, 2026. Lowest published fares: $321 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 26–30, 2026; $194 one way, Axel-exclusive, Frontier Airlines, 1 stop, Nov 26, 2026; 1 adult, economy, checked Nov 12, 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, labelled with the check date 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 check dates already shown here.

Exact travel datesAirlineFlightsTimes, duration, stopsTotal pricePrice checked
2026-11-26 · one wayFrontier AirlinesF92871 + F9277905:01:00→11:33:00 8h 32m 1 stop via ATLAxel-exclusive $194Nov 12, 2026
2026-11-26 · one waySouthwest AirlinesWN3957 + WN185406:05:00→13:00:00 8h 55m 1 stop via TPAAxel-exclusive $269Nov 12, 2026
2026-11-26 → 2026-11-27Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $356Nov 12, 2026
2026-11-26 → 2026-11-27Southwest AirlinesWN3957 + WN1854 / WN14 + WN405206:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $494Nov 12, 2026
2026-11-26 → 2026-11-28Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $356Nov 12, 2026
2026-11-26 → 2026-11-28Southwest AirlinesWN3957 + WN1854 / WN3002 + WN412206:05:00→13:00:00 8h 55m 1 stop via TPA · 07:50:00→18:25:00 8h 35m 1 stop via STLAxel-exclusive $494Nov 12, 2026
2026-11-26 → 2026-11-29Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $356Nov 12, 2026
2026-11-26 → 2026-11-29Southwest AirlinesWN3957 + WN1854 / WN14 + WN405206:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $494Nov 12, 2026
2026-11-26 → 2026-11-30Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $321Nov 12, 2026
2026-11-26 → 2026-11-30Southwest AirlinesWN3957 + WN1854 / WN14 + WN405206:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $444Nov 12, 2026
2026-11-26 → 2026-12-01Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $321Nov 12, 2026
2026-11-26 → 2026-12-01Southwest AirlinesWN3957 + WN1854 / WN3048 + WN336306:05:00→13:00:00 8h 55m 1 stop via TPA · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $444Nov 12, 2026
2026-11-26 → 2026-12-02Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $321Nov 12, 2026
2026-11-26 → 2026-12-02Southwest AirlinesWN3957 + WN1854 / WN3048 + WN336306:05:00→13:00:00 8h 55m 1 stop via TPA · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $444Nov 12, 2026
2026-11-26 → 2026-12-03Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $321Nov 12, 2026
2026-11-26 → 2026-12-03Southwest AirlinesWN3957 + WN1854 / WN14 + WN405206:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $444Nov 12, 2026
2026-11-26 → 2026-12-04Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $321Nov 12, 2026
2026-11-26 → 2026-12-04Southwest AirlinesWN3957 + WN1854 / WN14 + WN405206:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $444Nov 12, 2026
2026-11-26 → 2026-12-05Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $321Nov 12, 2026
2026-11-26 → 2026-12-05Southwest AirlinesWN3957 + WN1854 / WN3002 + WN412206:05:00→13:00:00 8h 55m 1 stop via TPA · 07:50:00→18:25:00 8h 35m 1 stop via STLAxel-exclusive $444Nov 12, 2026
2026-11-26 → 2026-12-06Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $321Nov 12, 2026
2026-11-26 → 2026-12-06Southwest AirlinesWN3957 + WN1854 / WN14 + WN405206:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $444Nov 12, 2026
2026-11-26 → 2026-12-07Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $321Nov 12, 2026
2026-11-26 → 2026-12-07Southwest AirlinesWN3957 + WN1854 / WN14 + WN405206:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $444Nov 12, 2026
2026-11-26 → 2026-12-08Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $321Nov 12, 2026
2026-11-26 → 2026-12-08Southwest AirlinesWN3957 + WN1854 / WN3048 + WN336306:05:00→13:00:00 8h 55m 1 stop via TPA · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $444Nov 12, 2026
2026-11-26 → 2026-12-09Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $321Nov 12, 2026
2026-11-26 → 2026-12-09Southwest AirlinesWN3957 + WN1854 / WN3048 + WN336306:05:00→13:00:00 8h 55m 1 stop via TPA · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $444Nov 12, 2026
2026-11-26 → 2026-12-10Frontier AirlinesF92871 + F92779 / F92144 + F9230005:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATLAxel-exclusive $321Nov 12, 2026
2026-11-26 → 2026-12-10Southwest AirlinesWN3957 + WN1854 / WN3002 + WN412206:05:00→13:00:00 8h 55m 1 stop via TPA · 07:50:00→18:25:00 8h 35m 1 stop via STLAxel-exclusive $444Nov 12, 2026

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 nightly rate and the stay's total, from 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 (MDW) flight deals

2026-11-26 · one way · Axel-exclusive $194

  • Frontier Airlines F92871 / F92779: SJU 2026-11-26 05:01:00 → MDW 2026-11-26 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-26 05:01:00 → ATL 2026-11-26 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-26 10:27:00 → MDW 2026-11-26 11:33:00.

2026-11-26 · one way · Axel-exclusive $269

  • Southwest Airlines WN3957 / WN1854: SJU 2026-11-26 06:05:00 → MDW 2026-11-26 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-11-26 06:05:00 → TPA 2026-11-26 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-11-26 11:15:00 → MDW 2026-11-26 13:00:00.

2026-11-26 → 2026-11-27 · Axel-exclusive $356

  • Frontier Airlines F92871 / F92779: SJU 2026-11-26 05:01:00 → MDW 2026-11-26 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-26 05:01:00 → ATL 2026-11-26 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-26 10:27:00 → MDW 2026-11-26 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-11-27 13:11:00 → SJU 2026-11-27 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-11-27 13:11:00 → ATL 2026-11-27 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-11-27 19:06:00 → SJU 2026-11-27 23:44:00.

2026-11-26 → 2026-11-27 · Axel-exclusive $494

  • Southwest Airlines WN3957 / WN1854: SJU 2026-11-26 06:05:00 → MDW 2026-11-26 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-11-26 06:05:00 → TPA 2026-11-26 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-11-26 11:15:00 → MDW 2026-11-26 13:00:00.
  • Southwest Airlines WN14 / WN4052: MDW 2026-11-27 14:30:00 → SJU 2026-11-28 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
    • WN14: MDW 2026-11-27 14:30:00 → BWI 2026-11-27 17:15:00; layover at BWI: 160 minutes.
    • WN4052: BWI 2026-11-27 19:55:00 → SJU 2026-11-28 01:00:00.

2026-11-26 → 2026-11-28 · Axel-exclusive $356

  • Frontier Airlines F92871 / F92779: SJU 2026-11-26 05:01:00 → MDW 2026-11-26 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-26 05:01:00 → ATL 2026-11-26 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-26 10:27:00 → MDW 2026-11-26 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-11-28 13:11:00 → SJU 2026-11-28 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-11-28 13:11:00 → ATL 2026-11-28 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-11-28 19:06:00 → SJU 2026-11-28 23:44:00.

2026-11-26 → 2026-11-28 · Axel-exclusive $494

  • Southwest Airlines WN3957 / WN1854: SJU 2026-11-26 06:05:00 → MDW 2026-11-26 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-11-26 06:05:00 → TPA 2026-11-26 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-11-26 11:15:00 → MDW 2026-11-26 13:00:00.
  • Southwest Airlines WN3002 / WN4122: MDW 2026-11-28 07:50:00 → SJU 2026-11-28 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
    • WN3002: MDW 2026-11-28 07:50:00 → STL 2026-11-28 09:10:00; layover at STL: 175 minutes.
    • WN4122: STL 2026-11-28 12:05:00 → SJU 2026-11-28 18:25:00.

2026-11-26 → 2026-11-29 · Axel-exclusive $356

  • Frontier Airlines F92871 / F92779: SJU 2026-11-26 05:01:00 → MDW 2026-11-26 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-26 05:01:00 → ATL 2026-11-26 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-26 10:27:00 → MDW 2026-11-26 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-11-29 13:11:00 → SJU 2026-11-29 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-11-29 13:11:00 → ATL 2026-11-29 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-11-29 19:06:00 → SJU 2026-11-29 23:44:00.

2026-11-26 → 2026-11-29 · Axel-exclusive $494

  • Southwest Airlines WN3957 / WN1854: SJU 2026-11-26 06:05:00 → MDW 2026-11-26 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-11-26 06:05:00 → TPA 2026-11-26 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-11-26 11:15:00 → MDW 2026-11-26 13:00:00.
  • Southwest Airlines WN14 / WN4052: MDW 2026-11-29 14:30:00 → SJU 2026-11-30 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
    • WN14: MDW 2026-11-29 14:30:00 → BWI 2026-11-29 17:15:00; layover at BWI: 160 minutes.
    • WN4052: BWI 2026-11-29 19:55:00 → SJU 2026-11-30 01:00:00.

2026-11-26 → 2026-11-30 · Axel-exclusive $321

  • Frontier Airlines F92871 / F92779: SJU 2026-11-26 05:01:00 → MDW 2026-11-26 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-26 05:01:00 → ATL 2026-11-26 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-26 10:27:00 → MDW 2026-11-26 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-11-30 13:11:00 → SJU 2026-11-30 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-11-30 13:11:00 → ATL 2026-11-30 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-11-30 19:06:00 → SJU 2026-11-30 23:44:00.

2026-11-26 → 2026-11-30 · Axel-exclusive $444

  • Southwest Airlines WN3957 / WN1854: SJU 2026-11-26 06:05:00 → MDW 2026-11-26 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-11-26 06:05:00 → TPA 2026-11-26 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-11-26 11:15:00 → MDW 2026-11-26 13:00:00.
  • Southwest Airlines WN14 / WN4052: MDW 2026-11-30 14:30:00 → SJU 2026-12-01 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
    • WN14: MDW 2026-11-30 14:30:00 → BWI 2026-11-30 17:15:00; layover at BWI: 160 minutes.
    • WN4052: BWI 2026-11-30 19:55:00 → SJU 2026-12-01 01:00:00.

2026-11-26 → 2026-12-02 · Axel-exclusive $321

  • Frontier Airlines F92871 / F92779: SJU 2026-11-26 05:01:00 → MDW 2026-11-26 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-26 05:01:00 → ATL 2026-11-26 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-26 10:27:00 → MDW 2026-11-26 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-12-02 13:11:00 → SJU 2026-12-02 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-12-02 13:11:00 → ATL 2026-12-02 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-12-02 19:06:00 → SJU 2026-12-02 23:44:00.

2026-11-26 → 2026-12-02 · Axel-exclusive $444

  • Southwest Airlines WN3957 / WN1854: SJU 2026-11-26 06:05:00 → MDW 2026-11-26 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-11-26 06:05:00 → TPA 2026-11-26 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-11-26 11:15:00 → MDW 2026-11-26 13:00:00.
  • Southwest Airlines WN3048 / WN3363: MDW 2026-12-02 13:20:00 → SJU 2026-12-02 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
    • WN3048: MDW 2026-12-02 13:20:00 → TPA 2026-12-02 16:55:00; layover at TPA: 80 minutes.
    • WN3363: TPA 2026-12-02 18:15:00 → SJU 2026-12-02 22:25:00.

2026-11-26 → 2026-12-03 · Axel-exclusive $321

  • Frontier Airlines F92871 / F92779: SJU 2026-11-26 05:01:00 → MDW 2026-11-26 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-26 05:01:00 → ATL 2026-11-26 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-26 10:27:00 → MDW 2026-11-26 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-12-03 13:11:00 → SJU 2026-12-03 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-12-03 13:11:00 → ATL 2026-12-03 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-12-03 19:06:00 → SJU 2026-12-03 23:44:00.

2026-11-26 → 2026-12-03 · Axel-exclusive $444

  • Southwest Airlines WN3957 / WN1854: SJU 2026-11-26 06:05:00 → MDW 2026-11-26 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-11-26 06:05:00 → TPA 2026-11-26 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-11-26 11:15:00 → MDW 2026-11-26 13:00:00.
  • Southwest Airlines WN14 / WN4052: MDW 2026-12-03 14:30:00 → SJU 2026-12-04 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
    • WN14: MDW 2026-12-03 14:30:00 → BWI 2026-12-03 17:15:00; layover at BWI: 160 minutes.
    • WN4052: BWI 2026-12-03 19:55:00 → SJU 2026-12-04 01:00:00.

2026-11-26 → 2026-12-04 · Axel-exclusive $321

  • Frontier Airlines F92871 / F92779: SJU 2026-11-26 05:01:00 → MDW 2026-11-26 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-26 05:01:00 → ATL 2026-11-26 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-26 10:27:00 → MDW 2026-11-26 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-12-04 13:11:00 → SJU 2026-12-04 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-12-04 13:11:00 → ATL 2026-12-04 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-12-04 19:06:00 → SJU 2026-12-04 23:44:00.

2026-11-26 → 2026-12-04 · Axel-exclusive $444

  • Southwest Airlines WN3957 / WN1854: SJU 2026-11-26 06:05:00 → MDW 2026-11-26 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-11-26 06:05:00 → TPA 2026-11-26 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-11-26 11:15:00 → MDW 2026-11-26 13:00:00.
  • Southwest Airlines WN14 / WN4052: MDW 2026-12-04 14:30:00 → SJU 2026-12-05 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
    • WN14: MDW 2026-12-04 14:30:00 → BWI 2026-12-04 17:15:00; layover at BWI: 160 minutes.
    • WN4052: BWI 2026-12-04 19:55:00 → SJU 2026-12-05 01:00:00.

2026-11-26 → 2026-12-06 · Axel-exclusive $321

  • Frontier Airlines F92871 / F92779: SJU 2026-11-26 05:01:00 → MDW 2026-11-26 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-26 05:01:00 → ATL 2026-11-26 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-26 10:27:00 → MDW 2026-11-26 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-12-06 13:11:00 → SJU 2026-12-06 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-12-06 13:11:00 → ATL 2026-12-06 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-12-06 19:06:00 → SJU 2026-12-06 23:44:00.

2026-11-26 → 2026-12-06 · Axel-exclusive $444

  • Southwest Airlines WN3957 / WN1854: SJU 2026-11-26 06:05:00 → MDW 2026-11-26 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-11-26 06:05:00 → TPA 2026-11-26 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-11-26 11:15:00 → MDW 2026-11-26 13:00:00.
  • Southwest Airlines WN14 / WN4052: MDW 2026-12-06 14:30:00 → SJU 2026-12-07 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
    • WN14: MDW 2026-12-06 14:30:00 → BWI 2026-12-06 17:15:00; layover at BWI: 160 minutes.
    • WN4052: BWI 2026-12-06 19:55:00 → SJU 2026-12-07 01:00:00.

2026-11-26 → 2026-12-07 · Axel-exclusive $321

  • Frontier Airlines F92871 / F92779: SJU 2026-11-26 05:01:00 → MDW 2026-11-26 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-26 05:01:00 → ATL 2026-11-26 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-26 10:27:00 → MDW 2026-11-26 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-12-07 13:11:00 → SJU 2026-12-07 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-12-07 13:11:00 → ATL 2026-12-07 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-12-07 19:06:00 → SJU 2026-12-07 23:44:00.

2026-11-26 → 2026-12-07 · Axel-exclusive $444

  • Southwest Airlines WN3957 / WN1854: SJU 2026-11-26 06:05:00 → MDW 2026-11-26 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-11-26 06:05:00 → TPA 2026-11-26 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-11-26 11:15:00 → MDW 2026-11-26 13:00:00.
  • Southwest Airlines WN14 / WN4052: MDW 2026-12-07 14:30:00 → SJU 2026-12-08 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
    • WN14: MDW 2026-12-07 14:30:00 → BWI 2026-12-07 17:15:00; layover at BWI: 160 minutes.
    • WN4052: BWI 2026-12-07 19:55:00 → SJU 2026-12-08 01:00:00.

2026-11-26 → 2026-12-08 · Axel-exclusive $321

  • Frontier Airlines F92871 / F92779: SJU 2026-11-26 05:01:00 → MDW 2026-11-26 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-26 05:01:00 → ATL 2026-11-26 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-26 10:27:00 → MDW 2026-11-26 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-12-08 13:11:00 → SJU 2026-12-08 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-12-08 13:11:00 → ATL 2026-12-08 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-12-08 19:06:00 → SJU 2026-12-08 23:44:00.

2026-11-26 → 2026-12-08 · Axel-exclusive $444

  • Southwest Airlines WN3957 / WN1854: SJU 2026-11-26 06:05:00 → MDW 2026-11-26 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-11-26 06:05:00 → TPA 2026-11-26 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-11-26 11:15:00 → MDW 2026-11-26 13:00:00.
  • Southwest Airlines WN3048 / WN3363: MDW 2026-12-08 13:20:00 → SJU 2026-12-08 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
    • WN3048: MDW 2026-12-08 13:20:00 → TPA 2026-12-08 16:55:00; layover at TPA: 80 minutes.
    • WN3363: TPA 2026-12-08 18:15:00 → SJU 2026-12-08 22:25:00.

2026-11-26 → 2026-12-10 · Axel-exclusive $321

  • Frontier Airlines F92871 / F92779: SJU 2026-11-26 05:01:00 → MDW 2026-11-26 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-26 05:01:00 → ATL 2026-11-26 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-26 10:27:00 → MDW 2026-11-26 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-12-10 13:11:00 → SJU 2026-12-10 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-12-10 13:11:00 → ATL 2026-12-10 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-12-10 19:06:00 → SJU 2026-12-10 23:44:00.

2026-11-26 → 2026-12-10 · Axel-exclusive $444

  • Southwest Airlines WN3957 / WN1854: SJU 2026-11-26 06:05:00 → MDW 2026-11-26 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-11-26 06:05:00 → TPA 2026-11-26 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-11-26 11:15:00 → MDW 2026-11-26 13:00:00.
  • Southwest Airlines WN3002 / WN4122: MDW 2026-12-10 07:50:00 → SJU 2026-12-10 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
    • WN3002: MDW 2026-12-10 07:50:00 → STL 2026-12-10 09:10:00; layover at STL: 175 minutes.
    • WN4122: STL 2026-12-10 12:05:00 → SJU 2026-12-10 18:25:00.

Explore this route

For AI assistants

  • This page: San Juan (SJU) to Chicago (MDW) · Nov 26, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. 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 nightly rate and the stay's total, from the lowest saved total 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 its displayed check date); 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 (MDW) 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.