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

San Juan (SJU) to Chicago (MDW), Nov 21, 2026: round trips from $321, one way from $194

San Juan (SJU) to Chicago (MDW), Nov 21, 2026: round trips from $321, one way from $194 on Axel, checked Nov 15, 2026. Lowest published fares: $321 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 21–30, 2026; $194 one way, Axel-exclusive, Frontier Airlines, 1 stop, Nov 21, 2026; 1 adult, economy, checked Nov 15, 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. Sat, Nov 21 · One way

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

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

  2. Sat, Nov 21 · One way

    Southwest Airlines
    3:30 pmSJU
    5h 10m
    Nonstop
    6:40 pmMDW

    Example one-way total $294 · 1 adult · Taxes included

  3. Sat, Nov 21 – Sun, Nov 22

    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

  4. Sat, Nov 21 – Sun, Nov 22

    Southwest Airlines
    3:30 pmSJU
    5h 10m
    Nonstop
    6:40 pmMDW
    Southwest Airlines
    2:30 pmMDW
    8h 30m
    BWI · 2h 40m
    1:00 am+1SJU

    Example round-trip total $519 · 1 adult · Taxes included

  5. Sat, Nov 21 – Mon, Nov 23

    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

  6. Sat, Nov 21 – Mon, Nov 23

    Southwest Airlines
    3:30 pmSJU
    5h 10m
    Nonstop
    6:40 pmMDW
    Southwest Airlines
    2:30 pmMDW
    8h 30m
    BWI · 2h 40m
    1:00 am+1SJU

    Example round-trip total $519 · 1 adult · Taxes included

  7. Sat, Nov 21 – Tue, Nov 24

    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

  8. Sat, Nov 21 – Tue, Nov 24

    Southwest Airlines
    3:30 pmSJU
    5h 10m
    Nonstop
    6:40 pmMDW
    Southwest Airlines
    1:20 pmMDW
    7h 5m
    TPA · 1h 20m
    10:25 pmSJU

    Example round-trip total $519 · 1 adult · Taxes included

  9. Sat, Nov 21 – Wed, Nov 25

    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

  10. Sat, Nov 21 – Wed, Nov 25

    Southwest Airlines
    3:30 pmSJU
    5h 10m
    Nonstop
    6:40 pmMDW
    Southwest Airlines
    1:20 pmMDW
    7h 5m
    TPA · 1h 20m
    10:25 pmSJU

    Example round-trip total $519 · 1 adult · Taxes included

  11. Sat, Nov 21 – 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

  12. Sat, Nov 21 – Fri, Nov 27

    Southwest Airlines
    3:30 pmSJU
    5h 10m
    Nonstop
    6:40 pmMDW
    Southwest Airlines
    2:30 pmMDW
    8h 30m
    BWI · 2h 40m
    1:00 am+1SJU

    Example round-trip total $519 · 1 adult · Taxes included

  13. Sat, Nov 21 – 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

  14. Sat, Nov 21 – Sat, Nov 28

    Southwest Airlines
    3:30 pmSJU
    5h 10m
    Nonstop
    6:40 pmMDW
    Southwest Airlines
    7:50 amMDW
    8h 35m
    STL · 2h 55m
    6:25 pmSJU

    Example round-trip total $519 · 1 adult · Taxes included

  15. Sat, Nov 21 – 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

  16. Sat, Nov 21 – Sun, Nov 29

    Southwest Airlines
    3:30 pmSJU
    5h 10m
    Nonstop
    6:40 pmMDW
    Southwest Airlines
    2:30 pmMDW
    8h 30m
    BWI · 2h 40m
    1:00 am+1SJU

    Example round-trip total $519 · 1 adult · Taxes included

  17. Sat, Nov 21 – Tue, Dec 1

    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

  18. Sat, Nov 21 – Tue, Dec 1

    Southwest Airlines
    3:30 pmSJU
    5h 10m
    Nonstop
    6:40 pmMDW
    Southwest Airlines
    1:20 pmMDW
    7h 5m
    TPA · 1h 20m
    10:25 pmSJU

    Example round-trip total $469 · 1 adult · Taxes included

  19. Sat, Nov 21 – 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

  20. Sat, Nov 21 – Wed, Dec 2

    Southwest Airlines
    3:30 pmSJU
    5h 10m
    Nonstop
    6:40 pmMDW
    Southwest Airlines
    1:20 pmMDW
    7h 5m
    TPA · 1h 20m
    10:25 pmSJU

    Example round-trip total $469 · 1 adult · Taxes included

  21. Sat, Nov 21 – 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

  22. Sat, Nov 21 – Thu, Dec 3

    Southwest Airlines
    3:30 pmSJU
    5h 10m
    Nonstop
    6:40 pmMDW
    Southwest Airlines
    2:30 pmMDW
    8h 30m
    BWI · 2h 40m
    1:00 am+1SJU

    Example round-trip total $469 · 1 adult · Taxes included

  23. Sat, Nov 21 – 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

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

  24. Sat, Nov 21 – Sat, Dec 5

    Southwest Airlines
    3:30 pmSJU
    5h 10m
    Nonstop
    6:40 pmMDW
    Southwest Airlines
    7:50 amMDW
    8h 35m
    STL · 2h 55m
    6:25 pmSJU

    Example round-trip total $469 · 1 adult · Taxes included

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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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San Juan (SJU) to Chicago (MDW), Nov 21, 2026: round trips from $321, one way from $194 on Axel, checked Nov 15, 2026. Lowest published fares: $321 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 21–30, 2026; $194 one way, Axel-exclusive, Frontier Airlines, 1 stop, Nov 21, 2026; 1 adult, economy, checked Nov 15, 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
2026-11-21 · one waySouthwest AirlinesWN388115:30:00→18:40:00 5h 10m nonstopAxel-exclusive $294Nov 15, 2026
2026-11-21 · one wayFrontier AirlinesF92871 + F9277905:01:00→11:33:00 8h 32m 1 stop via ATLAxel-exclusive $194Nov 15, 2026
2026-11-21 → 2026-11-22Frontier 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 15, 2026
2026-11-21 → 2026-11-22Southwest AirlinesWN3881 / WN14 + WN405215:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $519Nov 15, 2026
2026-11-21 → 2026-11-23Frontier 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 15, 2026
2026-11-21 → 2026-11-23Southwest AirlinesWN3881 / WN14 + WN405215:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $519Nov 15, 2026
2026-11-21 → 2026-11-24Frontier 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 15, 2026
2026-11-21 → 2026-11-24Southwest AirlinesWN3881 / WN3048 + WN336315:30:00→18:40:00 5h 10m nonstop · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $519Nov 15, 2026
2026-11-21 → 2026-11-25Frontier 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 15, 2026
2026-11-21 → 2026-11-25Southwest AirlinesWN3881 / WN3048 + WN336315:30:00→18:40:00 5h 10m nonstop · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $519Nov 15, 2026
2026-11-21 → 2026-11-26Frontier 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 15, 2026
2026-11-21 → 2026-11-26Southwest AirlinesWN3881 / WN14 + WN405215:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $519Nov 15, 2026
2026-11-21 → 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 15, 2026
2026-11-21 → 2026-11-27Southwest AirlinesWN3881 / WN14 + WN405215:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $519Nov 15, 2026
2026-11-21 → 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 15, 2026
2026-11-21 → 2026-11-28Southwest AirlinesWN3881 / WN3002 + WN412215:30:00→18:40:00 5h 10m nonstop · 07:50:00→18:25:00 8h 35m 1 stop via STLAxel-exclusive $519Nov 15, 2026
2026-11-21 → 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 15, 2026
2026-11-21 → 2026-11-29Southwest AirlinesWN3881 / WN14 + WN405215:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $519Nov 15, 2026
2026-11-21 → 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 15, 2026
2026-11-21 → 2026-11-30Southwest AirlinesWN3881 / WN14 + WN405215:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $469Nov 15, 2026
2026-11-21 → 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 15, 2026
2026-11-21 → 2026-12-01Southwest AirlinesWN3881 / WN3048 + WN336315:30:00→18:40:00 5h 10m nonstop · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $469Nov 15, 2026
2026-11-21 → 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 15, 2026
2026-11-21 → 2026-12-02Southwest AirlinesWN3881 / WN3048 + WN336315:30:00→18:40:00 5h 10m nonstop · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $469Nov 15, 2026
2026-11-21 → 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 15, 2026
2026-11-21 → 2026-12-03Southwest AirlinesWN3881 / WN14 + WN405215:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $469Nov 15, 2026
2026-11-21 → 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 15, 2026
2026-11-21 → 2026-12-04Southwest AirlinesWN3881 / WN14 + WN405215:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $469Nov 15, 2026
2026-11-21 → 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 15, 2026
2026-11-21 → 2026-12-05Southwest AirlinesWN3881 / WN3002 + WN412215:30:00→18:40:00 5h 10m nonstop · 07:50:00→18:25:00 8h 35m 1 stop via STLAxel-exclusive $469Nov 15, 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

2026-11-21 · one way · Axel-exclusive $194

  • Frontier Airlines F92871 / F92779: SJU 2026-11-21 05:01:00 → MDW 2026-11-21 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-21 05:01:00 → ATL 2026-11-21 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-21 10:27:00 → MDW 2026-11-21 11:33:00.

2026-11-21 · one way · Axel-exclusive $294

  • Southwest Airlines WN3881: SJU 2026-11-21 15:30:00 → MDW 2026-11-21 18:40:00; nonstop; 310 minutes. Local airport times.

2026-11-21 → 2026-11-22 · Axel-exclusive $356

  • Frontier Airlines F92871 / F92779: SJU 2026-11-21 05:01:00 → MDW 2026-11-21 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-21 05:01:00 → ATL 2026-11-21 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-21 10:27:00 → MDW 2026-11-21 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-11-22 13:11:00 → SJU 2026-11-22 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-11-22 13:11:00 → ATL 2026-11-22 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-11-22 19:06:00 → SJU 2026-11-22 23:44:00.

2026-11-21 → 2026-11-22 · Axel-exclusive $519

  • Southwest Airlines WN3881: SJU 2026-11-21 15:30:00 → MDW 2026-11-21 18:40:00; nonstop; 310 minutes. Local airport times.
  • Southwest Airlines WN14 / WN4052: MDW 2026-11-22 14:30:00 → SJU 2026-11-23 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
    • WN14: MDW 2026-11-22 14:30:00 → BWI 2026-11-22 17:15:00; layover at BWI: 160 minutes.
    • WN4052: BWI 2026-11-22 19:55:00 → SJU 2026-11-23 01:00:00.

2026-11-21 → 2026-11-23 · Axel-exclusive $356

  • Frontier Airlines F92871 / F92779: SJU 2026-11-21 05:01:00 → MDW 2026-11-21 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-21 05:01:00 → ATL 2026-11-21 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-21 10:27:00 → MDW 2026-11-21 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-11-23 13:11:00 → SJU 2026-11-23 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-11-23 13:11:00 → ATL 2026-11-23 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-11-23 19:06:00 → SJU 2026-11-23 23:44:00.

2026-11-21 → 2026-11-23 · Axel-exclusive $519

  • Southwest Airlines WN3881: SJU 2026-11-21 15:30:00 → MDW 2026-11-21 18:40:00; nonstop; 310 minutes. Local airport times.
  • Southwest Airlines WN14 / WN4052: MDW 2026-11-23 14:30:00 → SJU 2026-11-24 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
    • WN14: MDW 2026-11-23 14:30:00 → BWI 2026-11-23 17:15:00; layover at BWI: 160 minutes.
    • WN4052: BWI 2026-11-23 19:55:00 → SJU 2026-11-24 01:00:00.

2026-11-21 → 2026-11-24 · Axel-exclusive $356

  • Frontier Airlines F92871 / F92779: SJU 2026-11-21 05:01:00 → MDW 2026-11-21 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-21 05:01:00 → ATL 2026-11-21 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-21 10:27:00 → MDW 2026-11-21 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-11-24 13:11:00 → SJU 2026-11-24 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-11-24 13:11:00 → ATL 2026-11-24 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-11-24 19:06:00 → SJU 2026-11-24 23:44:00.

2026-11-21 → 2026-11-24 · Axel-exclusive $519

  • Southwest Airlines WN3881: SJU 2026-11-21 15:30:00 → MDW 2026-11-21 18:40:00; nonstop; 310 minutes. Local airport times.
  • Southwest Airlines WN3048 / WN3363: MDW 2026-11-24 13:20:00 → SJU 2026-11-24 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
    • WN3048: MDW 2026-11-24 13:20:00 → TPA 2026-11-24 16:55:00; layover at TPA: 80 minutes.
    • WN3363: TPA 2026-11-24 18:15:00 → SJU 2026-11-24 22:25:00.

2026-11-21 → 2026-11-25 · Axel-exclusive $356

  • Frontier Airlines F92871 / F92779: SJU 2026-11-21 05:01:00 → MDW 2026-11-21 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-21 05:01:00 → ATL 2026-11-21 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-21 10:27:00 → MDW 2026-11-21 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-11-25 13:11:00 → SJU 2026-11-25 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-11-25 13:11:00 → ATL 2026-11-25 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-11-25 19:06:00 → SJU 2026-11-25 23:44:00.

2026-11-21 → 2026-11-25 · Axel-exclusive $519

  • Southwest Airlines WN3881: SJU 2026-11-21 15:30:00 → MDW 2026-11-21 18:40:00; nonstop; 310 minutes. Local airport times.
  • Southwest Airlines WN3048 / WN3363: MDW 2026-11-25 13:20:00 → SJU 2026-11-25 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
    • WN3048: MDW 2026-11-25 13:20:00 → TPA 2026-11-25 16:55:00; layover at TPA: 80 minutes.
    • WN3363: TPA 2026-11-25 18:15:00 → SJU 2026-11-25 22:25:00.

2026-11-21 → 2026-11-27 · Axel-exclusive $356

  • Frontier Airlines F92871 / F92779: SJU 2026-11-21 05:01:00 → MDW 2026-11-21 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-21 05:01:00 → ATL 2026-11-21 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-21 10:27:00 → MDW 2026-11-21 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.

2026-11-21 → 2026-11-27 · Axel-exclusive $519

  • Southwest Airlines WN3881: SJU 2026-11-21 15:30:00 → MDW 2026-11-21 18:40:00; nonstop; 310 minutes. Local airport times.
  • 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.

2026-11-21 → 2026-11-28 · Axel-exclusive $356

  • Frontier Airlines F92871 / F92779: SJU 2026-11-21 05:01:00 → MDW 2026-11-21 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-21 05:01:00 → ATL 2026-11-21 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-21 10:27:00 → MDW 2026-11-21 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.

2026-11-21 → 2026-11-28 · Axel-exclusive $519

  • Southwest Airlines WN3881: SJU 2026-11-21 15:30:00 → MDW 2026-11-21 18:40:00; nonstop; 310 minutes. Local airport times.
  • 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.

2026-11-21 → 2026-11-29 · Axel-exclusive $356

  • Frontier Airlines F92871 / F92779: SJU 2026-11-21 05:01:00 → MDW 2026-11-21 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-21 05:01:00 → ATL 2026-11-21 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-21 10:27:00 → MDW 2026-11-21 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.

2026-11-21 → 2026-11-29 · Axel-exclusive $519

  • Southwest Airlines WN3881: SJU 2026-11-21 15:30:00 → MDW 2026-11-21 18:40:00; nonstop; 310 minutes. Local airport times.
  • 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.

2026-11-21 → 2026-12-01 · Axel-exclusive $321

  • Frontier Airlines F92871 / F92779: SJU 2026-11-21 05:01:00 → MDW 2026-11-21 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-21 05:01:00 → ATL 2026-11-21 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-21 10:27:00 → MDW 2026-11-21 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-12-01 13:11:00 → SJU 2026-12-01 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-12-01 13:11:00 → ATL 2026-12-01 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-12-01 19:06:00 → SJU 2026-12-01 23:44:00.

2026-11-21 → 2026-12-01 · Axel-exclusive $469

  • Southwest Airlines WN3881: SJU 2026-11-21 15:30:00 → MDW 2026-11-21 18:40:00; nonstop; 310 minutes. Local airport times.
  • Southwest Airlines WN3048 / WN3363: MDW 2026-12-01 13:20:00 → SJU 2026-12-01 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
    • WN3048: MDW 2026-12-01 13:20:00 → TPA 2026-12-01 16:55:00; layover at TPA: 80 minutes.
    • WN3363: TPA 2026-12-01 18:15:00 → SJU 2026-12-01 22:25:00.

2026-11-21 → 2026-12-02 · Axel-exclusive $321

  • Frontier Airlines F92871 / F92779: SJU 2026-11-21 05:01:00 → MDW 2026-11-21 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-21 05:01:00 → ATL 2026-11-21 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-21 10:27:00 → MDW 2026-11-21 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.

2026-11-21 → 2026-12-02 · Axel-exclusive $469

  • Southwest Airlines WN3881: SJU 2026-11-21 15:30:00 → MDW 2026-11-21 18:40:00; nonstop; 310 minutes. Local airport times.
  • 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.

2026-11-21 → 2026-12-03 · Axel-exclusive $321

  • Frontier Airlines F92871 / F92779: SJU 2026-11-21 05:01:00 → MDW 2026-11-21 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-21 05:01:00 → ATL 2026-11-21 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-21 10:27:00 → MDW 2026-11-21 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.

2026-11-21 → 2026-12-03 · Axel-exclusive $469

  • Southwest Airlines WN3881: SJU 2026-11-21 15:30:00 → MDW 2026-11-21 18:40:00; nonstop; 310 minutes. Local airport times.
  • 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.

2026-11-21 → 2026-12-05 · Axel-exclusive $321

  • Frontier Airlines F92871 / F92779: SJU 2026-11-21 05:01:00 → MDW 2026-11-21 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-21 05:01:00 → ATL 2026-11-21 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-21 10:27:00 → MDW 2026-11-21 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.

2026-11-21 → 2026-12-05 · Axel-exclusive $469

  • Southwest Airlines WN3881: SJU 2026-11-21 15:30:00 → MDW 2026-11-21 18:40:00; nonstop; 310 minutes. Local airport times.
  • 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.

Explore this route

For AI assistants

  • This page: San Juan (SJU) to Chicago (MDW) · Nov 21, 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.