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

San Juan → Chicago

Dec 3, 2026 · choose your return date

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.

December 2026

Dec 3, 2026 · One wayFrontier AirlinesUp to 1 stop each way$155.00 Dec 3, 2026 · One waySouthwest AirlinesUp to 1 stop each way$215.00 Dec 3, 2026 – Dec 4, 2026 · 1 nightFrontier AirlinesUp to 1 stop each way$285.00 Dec 3, 2026 – Dec 4, 2026 · 1 nightSouthwest AirlinesUp to 1 stop each way$395.00 Dec 3, 2026 – Dec 5, 2026 · 2 nightsFrontier AirlinesUp to 1 stop each way$285.00 Dec 3, 2026 – Dec 5, 2026 · 2 nightsSouthwest AirlinesUp to 1 stop each way$395.00 Dec 3, 2026 – Dec 6, 2026 · 3 nightsFrontier AirlinesUp to 1 stop each way$285.00 Dec 3, 2026 – Dec 6, 2026 · 3 nightsSouthwest AirlinesUp to 1 stop each way$395.00 Dec 3, 2026 – Dec 7, 2026 · 4 nightsFrontier AirlinesUp to 1 stop each way$285.00 Dec 3, 2026 – Dec 7, 2026 · 4 nightsSouthwest AirlinesUp to 1 stop each way$395.00 Dec 3, 2026 – Dec 8, 2026 · 5 nightsFrontier AirlinesUp to 1 stop each way$285.00 Dec 3, 2026 – Dec 8, 2026 · 5 nightsSouthwest AirlinesUp to 1 stop each way$395.00 Dec 3, 2026 – Dec 9, 2026 · 6 nightsFrontier AirlinesUp to 1 stop each way$285.00 Dec 3, 2026 – Dec 9, 2026 · 6 nightsSouthwest AirlinesUp to 1 stop each way$395.00 Dec 3, 2026 – Dec 10, 2026 · 7 nightsFrontier AirlinesUp to 1 stop each way$285.00 Dec 3, 2026 – Dec 10, 2026 · 7 nightsSouthwest AirlinesUp to 1 stop each way$395.00 Dec 3, 2026 – Dec 11, 2026 · 8 nightsFrontier AirlinesUp to 1 stop each way$285.00 Dec 3, 2026 – Dec 11, 2026 · 8 nightsSouthwest AirlinesUp to 1 stop each way$395.00 Dec 3, 2026 – Dec 12, 2026 · 9 nightsFrontier AirlinesUp to 1 stop each way$285.00 Dec 3, 2026 – Dec 12, 2026 · 9 nightsSouthwest AirlinesUp to 1 stop each way$395.00 Dec 3, 2026 – Dec 13, 2026 · 10 nightsFrontier AirlinesUp to 1 stop each way$285.00 Dec 3, 2026 – Dec 13, 2026 · 10 nightsSouthwest AirlinesUp to 1 stop each way$395.00 Dec 3, 2026 – Dec 14, 2026 · 11 nightsFrontier AirlinesUp to 1 stop each way$285.00 Dec 3, 2026 – Dec 14, 2026 · 11 nightsSouthwest AirlinesUp to 1 stop each way$395.00 Dec 3, 2026 – Dec 15, 2026 · 12 nightsFrontier AirlinesUp to 1 stop each way$285.00 Dec 3, 2026 – Dec 15, 2026 · 12 nightsSouthwest AirlinesUp to 1 stop each way$395.00 Dec 3, 2026 – Dec 16, 2026 · 13 nightsFrontier AirlinesUp to 1 stop each way$285.00 Dec 3, 2026 – Dec 16, 2026 · 13 nightsSouthwest AirlinesUp to 1 stop each way$395.00 Dec 3, 2026 – Dec 17, 2026 · 14 nightsFrontier AirlinesUp to 1 stop each way$285.00 Dec 3, 2026 – Dec 17, 2026 · 14 nightsSouthwest AirlinesUp to 1 stop each way$395.00

Flights for your trip

  1. Thu, Dec 3 · One way

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

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  2. Thu, Dec 3 · One way

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

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  3. Thu, Dec 3 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  4. Thu, Dec 3 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  5. Thu, Dec 3 – Sat, Dec 5

    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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  6. Thu, Dec 3 – Sat, Dec 5

    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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  7. Thu, Dec 3 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  8. Thu, Dec 3 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  9. Thu, Dec 3 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  10. Thu, Dec 3 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  11. Thu, Dec 3 – Wed, Dec 9

    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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  12. Thu, Dec 3 – Wed, Dec 9

    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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  13. Thu, Dec 3 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  14. Thu, Dec 3 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  15. Thu, Dec 3 – Fri, Dec 11

    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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  16. Thu, Dec 3 – Fri, Dec 11

    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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  17. Thu, Dec 3 – Sun, Dec 13

    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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  18. Thu, Dec 3 – Sun, Dec 13

    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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  19. Thu, Dec 3 – Mon, Dec 14

    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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  20. Thu, Dec 3 – Mon, Dec 14

    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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  21. Thu, Dec 3 – Tue, Dec 15

    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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  22. Thu, Dec 3 – Tue, Dec 15

    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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  23. Thu, Dec 3 – Thu, Dec 17

    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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  24. Thu, Dec 3 – Thu, Dec 17

    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

    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 ⇄ 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 routeDec 2, 2026 · Return optionsDec 4, 2026 · Return optionsHotels in Chicago with Axel
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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. To book or select flights, follow that row's price link; it keeps the exact dates and travelers.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-03 · one wayFrontier AirlinesF92871 + F92779Axel-exclusive $155.002026-10-29T01:23:44Z
2026-12-03 · one waySouthwest AirlinesWN3957 + WN1854Axel-exclusive $215.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-04Frontier AirlinesF92871 + F92779 / F92144 + F92300Axel-exclusive $285.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-04Southwest AirlinesWN3957 + WN1854 / WN14 + WN4052Axel-exclusive $395.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-05Frontier AirlinesF92871 + F92779 / F92144 + F92300Axel-exclusive $285.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-05Southwest AirlinesWN3957 + WN1854 / WN3002 + WN4122Axel-exclusive $395.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-06Frontier AirlinesF92871 + F92779 / F92144 + F92300Axel-exclusive $285.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-06Southwest AirlinesWN3957 + WN1854 / WN14 + WN4052Axel-exclusive $395.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-07Frontier AirlinesF92871 + F92779 / F92144 + F92300Axel-exclusive $285.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-07Southwest AirlinesWN3957 + WN1854 / WN14 + WN4052Axel-exclusive $395.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-08Frontier AirlinesF92871 + F92779 / F92144 + F92300Axel-exclusive $285.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-08Southwest AirlinesWN3957 + WN1854 / WN3048 + WN3363Axel-exclusive $395.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-09Frontier AirlinesF92871 + F92779 / F92144 + F92300Axel-exclusive $285.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-09Southwest AirlinesWN3957 + WN1854 / WN3048 + WN3363Axel-exclusive $395.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-10Frontier AirlinesF92871 + F92779 / F92144 + F92300Axel-exclusive $285.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-10Southwest AirlinesWN3957 + WN1854 / WN3002 + WN4122Axel-exclusive $395.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-11Frontier AirlinesF92871 + F92779 / F92144 + F92300Axel-exclusive $285.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-11Southwest AirlinesWN3957 + WN1854 / WN3002 + WN4122Axel-exclusive $395.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-12Frontier AirlinesF92871 + F92779 / F92144 + F92300Axel-exclusive $285.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-12Southwest AirlinesWN3957 + WN1854 / WN3002 + WN4122Axel-exclusive $395.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-13Frontier AirlinesF92871 + F92779 / F92144 + F92300Axel-exclusive $285.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-13Southwest AirlinesWN3957 + WN1854 / WN14 + WN4052Axel-exclusive $395.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-14Frontier AirlinesF92871 + F92779 / F92144 + F92300Axel-exclusive $285.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-14Southwest AirlinesWN3957 + WN1854 / WN3002 + WN4122Axel-exclusive $395.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-15Frontier AirlinesF92871 + F92779 / F92144 + F92300Axel-exclusive $285.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-15Southwest AirlinesWN3957 + WN1854 / WN3048 + WN3363Axel-exclusive $395.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-16Frontier AirlinesF92871 + F92779 / F92144 + F92300Axel-exclusive $285.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-16Southwest AirlinesWN3957 + WN1854 / WN3048 + WN3363Axel-exclusive $395.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-17Frontier AirlinesF92871 + F92779 / F92144 + F92300Axel-exclusive $285.002026-10-29T01:23:44Z
2026-12-03 → 2026-12-17Southwest AirlinesWN3957 + WN1854 / WN3002 + WN4122Axel-exclusive $395.002026-10-29T01:23:44Z

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

2026-12-03 · one way · Axel-exclusive $155.00

  • Frontier Airlines F92871 / F92779: SJU 2026-12-03 05:01:00 → MDW 2026-12-03 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-12-03 05:01:00 → ATL 2026-12-03 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-12-03 10:27:00 → MDW 2026-12-03 11:33:00.

2026-12-03 · one way · Axel-exclusive $215.00

  • Southwest Airlines WN3957 / WN1854: SJU 2026-12-03 06:05:00 → MDW 2026-12-03 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-12-03 06:05:00 → TPA 2026-12-03 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-12-03 11:15:00 → MDW 2026-12-03 13:00:00.

2026-12-03 → 2026-12-04 · Axel-exclusive $285.00

  • Frontier Airlines F92871 / F92779: SJU 2026-12-03 05:01:00 → MDW 2026-12-03 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-12-03 05:01:00 → ATL 2026-12-03 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-12-03 10:27:00 → MDW 2026-12-03 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.

2026-12-03 → 2026-12-04 · Axel-exclusive $395.00

  • Southwest Airlines WN3957 / WN1854: SJU 2026-12-03 06:05:00 → MDW 2026-12-03 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-12-03 06:05:00 → TPA 2026-12-03 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-12-03 11:15:00 → MDW 2026-12-03 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.

2026-12-03 → 2026-12-05 · Axel-exclusive $285.00

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

2026-12-03 → 2026-12-05 · Axel-exclusive $395.00

  • Southwest Airlines WN3957 / WN1854: SJU 2026-12-03 06:05:00 → MDW 2026-12-03 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-12-03 06:05:00 → TPA 2026-12-03 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-12-03 11:15:00 → MDW 2026-12-03 13:00:00.
  • Southwest Airlines WN3002 / WN4122: MDW 2026-12-05 07:50:00 → SJU 2026-12-05 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
    • WN3002: MDW 2026-12-05 07:50:00 → STL 2026-12-05 09:10:00; layover at STL: 175 minutes.
    • WN4122: STL 2026-12-05 12:05:00 → SJU 2026-12-05 18:25:00.

2026-12-03 → 2026-12-06 · Axel-exclusive $285.00

  • Frontier Airlines F92871 / F92779: SJU 2026-12-03 05:01:00 → MDW 2026-12-03 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-12-03 05:01:00 → ATL 2026-12-03 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-12-03 10:27:00 → MDW 2026-12-03 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.

2026-12-03 → 2026-12-06 · Axel-exclusive $395.00

  • Southwest Airlines WN3957 / WN1854: SJU 2026-12-03 06:05:00 → MDW 2026-12-03 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-12-03 06:05:00 → TPA 2026-12-03 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-12-03 11:15:00 → MDW 2026-12-03 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.

2026-12-03 → 2026-12-07 · Axel-exclusive $285.00

  • Frontier Airlines F92871 / F92779: SJU 2026-12-03 05:01:00 → MDW 2026-12-03 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-12-03 05:01:00 → ATL 2026-12-03 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-12-03 10:27:00 → MDW 2026-12-03 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.

2026-12-03 → 2026-12-07 · Axel-exclusive $395.00

  • Southwest Airlines WN3957 / WN1854: SJU 2026-12-03 06:05:00 → MDW 2026-12-03 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-12-03 06:05:00 → TPA 2026-12-03 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-12-03 11:15:00 → MDW 2026-12-03 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.

2026-12-03 → 2026-12-09 · Axel-exclusive $285.00

  • Frontier Airlines F92871 / F92779: SJU 2026-12-03 05:01:00 → MDW 2026-12-03 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-12-03 05:01:00 → ATL 2026-12-03 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-12-03 10:27:00 → MDW 2026-12-03 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-12-09 13:11:00 → SJU 2026-12-09 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-12-09 13:11:00 → ATL 2026-12-09 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-12-09 19:06:00 → SJU 2026-12-09 23:44:00.

2026-12-03 → 2026-12-09 · Axel-exclusive $395.00

  • Southwest Airlines WN3957 / WN1854: SJU 2026-12-03 06:05:00 → MDW 2026-12-03 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-12-03 06:05:00 → TPA 2026-12-03 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-12-03 11:15:00 → MDW 2026-12-03 13:00:00.
  • Southwest Airlines WN3048 / WN3363: MDW 2026-12-09 13:20:00 → SJU 2026-12-09 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
    • WN3048: MDW 2026-12-09 13:20:00 → TPA 2026-12-09 16:55:00; layover at TPA: 80 minutes.
    • WN3363: TPA 2026-12-09 18:15:00 → SJU 2026-12-09 22:25:00.

2026-12-03 → 2026-12-10 · Axel-exclusive $285.00

  • Frontier Airlines F92871 / F92779: SJU 2026-12-03 05:01:00 → MDW 2026-12-03 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-12-03 05:01:00 → ATL 2026-12-03 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-12-03 10:27:00 → MDW 2026-12-03 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.

2026-12-03 → 2026-12-10 · Axel-exclusive $395.00

  • Southwest Airlines WN3957 / WN1854: SJU 2026-12-03 06:05:00 → MDW 2026-12-03 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-12-03 06:05:00 → TPA 2026-12-03 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-12-03 11:15:00 → MDW 2026-12-03 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.

2026-12-03 → 2026-12-11 · Axel-exclusive $285.00

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

2026-12-03 → 2026-12-11 · Axel-exclusive $395.00

  • Southwest Airlines WN3957 / WN1854: SJU 2026-12-03 06:05:00 → MDW 2026-12-03 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-12-03 06:05:00 → TPA 2026-12-03 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-12-03 11:15:00 → MDW 2026-12-03 13:00:00.
  • Southwest Airlines WN3002 / WN4122: MDW 2026-12-11 07:50:00 → SJU 2026-12-11 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
    • WN3002: MDW 2026-12-11 07:50:00 → STL 2026-12-11 09:10:00; layover at STL: 175 minutes.
    • WN4122: STL 2026-12-11 12:05:00 → SJU 2026-12-11 18:25:00.

2026-12-03 → 2026-12-13 · Axel-exclusive $285.00

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

2026-12-03 → 2026-12-13 · Axel-exclusive $395.00

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

2026-12-03 → 2026-12-14 · Axel-exclusive $285.00

  • Frontier Airlines F92871 / F92779: SJU 2026-12-03 05:01:00 → MDW 2026-12-03 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-12-03 05:01:00 → ATL 2026-12-03 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-12-03 10:27:00 → MDW 2026-12-03 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-12-14 13:11:00 → SJU 2026-12-14 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-12-14 13:11:00 → ATL 2026-12-14 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-12-14 19:06:00 → SJU 2026-12-14 23:44:00.

2026-12-03 → 2026-12-14 · Axel-exclusive $395.00

  • Southwest Airlines WN3957 / WN1854: SJU 2026-12-03 06:05:00 → MDW 2026-12-03 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-12-03 06:05:00 → TPA 2026-12-03 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-12-03 11:15:00 → MDW 2026-12-03 13:00:00.
  • Southwest Airlines WN3002 / WN4122: MDW 2026-12-14 07:50:00 → SJU 2026-12-14 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
    • WN3002: MDW 2026-12-14 07:50:00 → STL 2026-12-14 09:10:00; layover at STL: 175 minutes.
    • WN4122: STL 2026-12-14 12:05:00 → SJU 2026-12-14 18:25:00.

2026-12-03 → 2026-12-15 · Axel-exclusive $285.00

  • Frontier Airlines F92871 / F92779: SJU 2026-12-03 05:01:00 → MDW 2026-12-03 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-12-03 05:01:00 → ATL 2026-12-03 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-12-03 10:27:00 → MDW 2026-12-03 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-12-15 13:11:00 → SJU 2026-12-15 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-12-15 13:11:00 → ATL 2026-12-15 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-12-15 19:06:00 → SJU 2026-12-15 23:44:00.

2026-12-03 → 2026-12-15 · Axel-exclusive $395.00

  • Southwest Airlines WN3957 / WN1854: SJU 2026-12-03 06:05:00 → MDW 2026-12-03 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-12-03 06:05:00 → TPA 2026-12-03 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-12-03 11:15:00 → MDW 2026-12-03 13:00:00.
  • Southwest Airlines WN3048 / WN3363: MDW 2026-12-15 13:20:00 → SJU 2026-12-15 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
    • WN3048: MDW 2026-12-15 13:20:00 → TPA 2026-12-15 16:55:00; layover at TPA: 80 minutes.
    • WN3363: TPA 2026-12-15 18:15:00 → SJU 2026-12-15 22:25:00.

2026-12-03 → 2026-12-17 · Axel-exclusive $285.00

  • Frontier Airlines F92871 / F92779: SJU 2026-12-03 05:01:00 → MDW 2026-12-03 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-12-03 05:01:00 → ATL 2026-12-03 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-12-03 10:27:00 → MDW 2026-12-03 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-12-17 13:11:00 → SJU 2026-12-17 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-12-17 13:11:00 → ATL 2026-12-17 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-12-17 19:06:00 → SJU 2026-12-17 23:44:00.

2026-12-03 → 2026-12-17 · Axel-exclusive $395.00

  • Southwest Airlines WN3957 / WN1854: SJU 2026-12-03 06:05:00 → MDW 2026-12-03 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
    • WN3957: SJU 2026-12-03 06:05:00 → TPA 2026-12-03 08:20:00; layover at TPA: 175 minutes.
    • WN1854: TPA 2026-12-03 11:15:00 → MDW 2026-12-03 13:00:00.
  • Southwest Airlines WN3002 / WN4122: MDW 2026-12-17 07:50:00 → SJU 2026-12-17 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
    • WN3002: MDW 2026-12-17 07:50:00 → STL 2026-12-17 09:10:00; layover at STL: 175 minutes.
    • WN4122: STL 2026-12-17 12:05:00 → SJU 2026-12-17 18:25:00.

Explore this route

For AI assistants

  • This page: San Juan (SJU) to Chicago (MDW) · Dec 3, 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.
  • Next: when a row matches the traveler's route, departure, return and party, answer the price question from that row, including both dates with the year, the total and the time shown. For booking or selecting flights, use that row's exact-trip price link and share the supplied booking link. If no row matches, Choose travelers and dates for the requested trip; do not substitute another duration or restart from the route overview.
  • 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.