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

San Juan (SJU) to Chicago (MDW), Nov 18, 2026: round trips from $285, one way from $155

San Juan (SJU) to Chicago (MDW), Nov 18, 2026: round trips from $285, one way from $155 on Axel, checked Oct 29, 2026. Lowest published fares: $285 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 18–19, 2026; $155 one way, Axel-exclusive, Frontier Airlines, 1 stop, Nov 18, 2026; 1 adult, economy, checked Oct 29, 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. Wed, Nov 18 · 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. Wed, Nov 18 · One way

    Southwest Airlines
    5:35 amSJU
    8h 30m
    MCO · 2h 25m
    12:05 pmMDW

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  3. Wed, Nov 18 – Thu, Nov 19

    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. Wed, Nov 18 – Thu, Nov 19

    Southwest Airlines
    5:35 amSJU
    8h 30m
    MCO · 2h 25m
    12:05 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. Wed, Nov 18 – Fri, Nov 20

    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. Wed, Nov 18 – Fri, Nov 20

    Southwest Airlines
    5:35 amSJU
    8h 30m
    MCO · 2h 25m
    12:05 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.

  7. Wed, Nov 18 – Sat, Nov 21

    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. Wed, Nov 18 – Sat, Nov 21

    Southwest Airlines
    5:35 amSJU
    8h 30m
    MCO · 2h 25m
    12:05 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.

  9. Wed, Nov 18 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  10. Wed, Nov 18 – Sun, Nov 22

    Southwest Airlines
    5:35 amSJU
    8h 30m
    MCO · 2h 25m
    12:05 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. Wed, Nov 18 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  12. Wed, Nov 18 – Tue, Nov 24

    Southwest Airlines
    5:35 amSJU
    8h 30m
    MCO · 2h 25m
    12:05 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. Wed, Nov 18 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  14. Wed, Nov 18 – Wed, Nov 25

    Southwest Airlines
    5:35 amSJU
    8h 30m
    MCO · 2h 25m
    12:05 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.

  15. Wed, Nov 18 – Thu, Nov 26

    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. Wed, Nov 18 – Thu, Nov 26

    Southwest Airlines
    5:35 amSJU
    8h 30m
    MCO · 2h 25m
    12:05 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.

  17. Wed, Nov 18 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  18. Wed, Nov 18 – Sat, Nov 28

    Southwest Airlines
    5:35 amSJU
    8h 30m
    MCO · 2h 25m
    12:05 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.

  19. Wed, Nov 18 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  20. Wed, Nov 18 – Sun, Nov 29

    Southwest Airlines
    5:35 amSJU
    8h 30m
    MCO · 2h 25m
    12:05 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.

  21. Wed, Nov 18 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  22. Wed, Nov 18 – Mon, Nov 30

    Southwest Airlines
    5:35 amSJU
    8h 30m
    MCO · 2h 25m
    12:05 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.

  23. Wed, Nov 18 – 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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  24. Wed, Nov 18 – Wed, Dec 2

    Southwest Airlines
    5:35 amSJU
    8h 30m
    MCO · 2h 25m
    12:05 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.

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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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Explore this route

All dates for this routeNov 17, 2026 · Return optionsNov 19, 2026 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

San Juan (SJU) to Chicago (MDW), Nov 18, 2026: round trips from $285, one way from $155 on Axel, checked Oct 29, 2026. Lowest published fares: $285 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 18–19, 2026; $155 one way, Axel-exclusive, Frontier Airlines, 1 stop, Nov 18, 2026; 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

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

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

Exact travel datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2026-11-18 · one wayFrontier AirlinesF92871 + F9277905:01:00→11:33:00 8h 32m 1 stop via ATLAxel-exclusive $155.002026-10-29T01:23:44Z
2026-11-18 · one waySouthwest AirlinesWN4666 + WN280305:35:00→12:05:00 8h 30m 1 stop via MCOAxel-exclusive $215.002026-10-29T01:23:44Z
2026-11-18 → 2026-11-19Frontier 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 $285.002026-10-29T01:23:44Z
2026-11-18 → 2026-11-19Southwest AirlinesWN4666 + WN2803 / WN14 + WN405205:35:00→12:05:00 8h 30m 1 stop via MCO · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $395.002026-10-29T01:23:44Z
2026-11-18 → 2026-11-20Frontier 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 $285.002026-10-29T01:23:44Z
2026-11-18 → 2026-11-20Southwest AirlinesWN4666 + WN2803 / WN14 + WN405205:35:00→12:05:00 8h 30m 1 stop via MCO · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $395.002026-10-29T01:23:44Z
2026-11-18 → 2026-11-21Frontier 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 $320.632026-10-29T01:23:44Z
2026-11-18 → 2026-11-21Southwest AirlinesWN4666 + WN2803 / WN3002 + WN412205:35:00→12:05:00 8h 30m 1 stop via MCO · 07:50:00→18:25:00 8h 35m 1 stop via STLAxel-exclusive $444.382026-10-29T01:23:44Z
2026-11-18 → 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 $320.632026-10-29T01:23:44Z
2026-11-18 → 2026-11-22Southwest AirlinesWN4666 + WN2803 / WN14 + WN405205:35:00→12:05:00 8h 30m 1 stop via MCO · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $444.382026-10-29T01:23:44Z
2026-11-18 → 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 $320.632026-10-29T01:23:44Z
2026-11-18 → 2026-11-23Southwest AirlinesWN4666 + WN2803 / WN14 + WN405205:35:00→12:05:00 8h 30m 1 stop via MCO · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $444.382026-10-29T01:23:44Z
2026-11-18 → 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 $320.632026-10-29T01:23:44Z
2026-11-18 → 2026-11-24Southwest AirlinesWN4666 + WN2803 / WN3048 + WN336305:35:00→12:05:00 8h 30m 1 stop via MCO · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $444.382026-10-29T01:23:44Z
2026-11-18 → 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 $320.632026-10-29T01:23:44Z
2026-11-18 → 2026-11-25Southwest AirlinesWN4666 + WN2803 / WN3048 + WN336305:35:00→12:05:00 8h 30m 1 stop via MCO · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $444.382026-10-29T01:23:44Z
2026-11-18 → 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 $320.632026-10-29T01:23:44Z
2026-11-18 → 2026-11-26Southwest AirlinesWN4666 + WN2803 / WN14 + WN405205:35:00→12:05:00 8h 30m 1 stop via MCO · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $444.382026-10-29T01:23:44Z
2026-11-18 → 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 $320.632026-10-29T01:23:44Z
2026-11-18 → 2026-11-27Southwest AirlinesWN4666 + WN2803 / WN14 + WN405205:35:00→12:05:00 8h 30m 1 stop via MCO · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $444.382026-10-29T01:23:44Z
2026-11-18 → 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 $320.632026-10-29T01:23:44Z
2026-11-18 → 2026-11-28Southwest AirlinesWN4666 + WN2803 / WN3002 + WN412205:35:00→12:05:00 8h 30m 1 stop via MCO · 07:50:00→18:25:00 8h 35m 1 stop via STLAxel-exclusive $444.382026-10-29T01:23:44Z
2026-11-18 → 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 $320.632026-10-29T01:23:44Z
2026-11-18 → 2026-11-29Southwest AirlinesWN4666 + WN2803 / WN14 + WN405205:35:00→12:05:00 8h 30m 1 stop via MCO · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $444.382026-10-29T01:23:44Z
2026-11-18 → 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 $285.002026-10-29T01:23:44Z
2026-11-18 → 2026-11-30Southwest AirlinesWN4666 + WN2803 / WN14 + WN405205:35:00→12:05:00 8h 30m 1 stop via MCO · 14:30:00→01:00:00 8h 30m 1 stop via BWIAxel-exclusive $395.002026-10-29T01:23:44Z
2026-11-18 → 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 $285.002026-10-29T01:23:44Z
2026-11-18 → 2026-12-01Southwest AirlinesWN4666 + WN2803 / WN3048 + WN336305:35:00→12:05:00 8h 30m 1 stop via MCO · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $395.002026-10-29T01:23:44Z
2026-11-18 → 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 $285.002026-10-29T01:23:44Z
2026-11-18 → 2026-12-02Southwest AirlinesWN4666 + WN2803 / WN3048 + WN336305:35:00→12:05:00 8h 30m 1 stop via MCO · 13:20:00→22:25:00 7h 05m 1 stop via TPAAxel-exclusive $395.002026-10-29T01:23:44Z

Hotels in Chicago for these trips

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

All hotels in Chicago

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

2026-11-18 · one way · Axel-exclusive $155.00

  • Frontier Airlines F92871 / F92779: SJU 2026-11-18 05:01:00 → MDW 2026-11-18 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-18 05:01:00 → ATL 2026-11-18 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-18 10:27:00 → MDW 2026-11-18 11:33:00.

2026-11-18 · one way · Axel-exclusive $215.00

  • Southwest Airlines WN4666 / WN2803: SJU 2026-11-18 05:35:00 → MDW 2026-11-18 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
    • WN4666: SJU 2026-11-18 05:35:00 → MCO 2026-11-18 07:45:00; layover at MCO: 145 minutes.
    • WN2803: MCO 2026-11-18 10:10:00 → MDW 2026-11-18 12:05:00.

2026-11-18 → 2026-11-19 · Axel-exclusive $285.00

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

2026-11-18 → 2026-11-19 · Axel-exclusive $395.00

  • Southwest Airlines WN4666 / WN2803: SJU 2026-11-18 05:35:00 → MDW 2026-11-18 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
    • WN4666: SJU 2026-11-18 05:35:00 → MCO 2026-11-18 07:45:00; layover at MCO: 145 minutes.
    • WN2803: MCO 2026-11-18 10:10:00 → MDW 2026-11-18 12:05:00.
  • Southwest Airlines WN14 / WN4052: MDW 2026-11-19 14:30:00 → SJU 2026-11-20 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
    • WN14: MDW 2026-11-19 14:30:00 → BWI 2026-11-19 17:15:00; layover at BWI: 160 minutes.
    • WN4052: BWI 2026-11-19 19:55:00 → SJU 2026-11-20 01:00:00.

2026-11-18 → 2026-11-20 · Axel-exclusive $285.00

  • Frontier Airlines F92871 / F92779: SJU 2026-11-18 05:01:00 → MDW 2026-11-18 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-18 05:01:00 → ATL 2026-11-18 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-18 10:27:00 → MDW 2026-11-18 11:33:00.
  • Frontier Airlines F92144 / F92300: MDW 2026-11-20 13:11:00 → SJU 2026-11-20 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
    • F92144: MDW 2026-11-20 13:11:00 → ATL 2026-11-20 16:18:00; layover at ATL: 168 minutes.
    • F92300: ATL 2026-11-20 19:06:00 → SJU 2026-11-20 23:44:00.

2026-11-18 → 2026-11-20 · Axel-exclusive $395.00

  • Southwest Airlines WN4666 / WN2803: SJU 2026-11-18 05:35:00 → MDW 2026-11-18 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
    • WN4666: SJU 2026-11-18 05:35:00 → MCO 2026-11-18 07:45:00; layover at MCO: 145 minutes.
    • WN2803: MCO 2026-11-18 10:10:00 → MDW 2026-11-18 12:05:00.
  • Southwest Airlines WN14 / WN4052: MDW 2026-11-20 14:30:00 → SJU 2026-11-21 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
    • WN14: MDW 2026-11-20 14:30:00 → BWI 2026-11-20 17:15:00; layover at BWI: 160 minutes.
    • WN4052: BWI 2026-11-20 19:55:00 → SJU 2026-11-21 01:00:00.

2026-11-18 → 2026-11-21 · Axel-exclusive $320.63

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

2026-11-18 → 2026-11-21 · Axel-exclusive $444.38

  • Southwest Airlines WN4666 / WN2803: SJU 2026-11-18 05:35:00 → MDW 2026-11-18 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
    • WN4666: SJU 2026-11-18 05:35:00 → MCO 2026-11-18 07:45:00; layover at MCO: 145 minutes.
    • WN2803: MCO 2026-11-18 10:10:00 → MDW 2026-11-18 12:05:00.
  • Southwest Airlines WN3002 / WN4122: MDW 2026-11-21 07:50:00 → SJU 2026-11-21 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times.
    • WN3002: MDW 2026-11-21 07:50:00 → STL 2026-11-21 09:10:00; layover at STL: 175 minutes.
    • WN4122: STL 2026-11-21 12:05:00 → SJU 2026-11-21 18:25:00.

2026-11-18 → 2026-11-22 · Axel-exclusive $320.63

  • Frontier Airlines F92871 / F92779: SJU 2026-11-18 05:01:00 → MDW 2026-11-18 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-18 05:01:00 → ATL 2026-11-18 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-18 10:27:00 → MDW 2026-11-18 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.

2026-11-18 → 2026-11-22 · Axel-exclusive $444.38

  • Southwest Airlines WN4666 / WN2803: SJU 2026-11-18 05:35:00 → MDW 2026-11-18 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
    • WN4666: SJU 2026-11-18 05:35:00 → MCO 2026-11-18 07:45:00; layover at MCO: 145 minutes.
    • WN2803: MCO 2026-11-18 10:10:00 → MDW 2026-11-18 12:05:00.
  • 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.

2026-11-18 → 2026-11-24 · Axel-exclusive $320.63

  • Frontier Airlines F92871 / F92779: SJU 2026-11-18 05:01:00 → MDW 2026-11-18 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-18 05:01:00 → ATL 2026-11-18 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-18 10:27:00 → MDW 2026-11-18 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.

2026-11-18 → 2026-11-24 · Axel-exclusive $444.38

  • Southwest Airlines WN4666 / WN2803: SJU 2026-11-18 05:35:00 → MDW 2026-11-18 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
    • WN4666: SJU 2026-11-18 05:35:00 → MCO 2026-11-18 07:45:00; layover at MCO: 145 minutes.
    • WN2803: MCO 2026-11-18 10:10:00 → MDW 2026-11-18 12:05:00.
  • 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.

2026-11-18 → 2026-11-25 · Axel-exclusive $320.63

  • Frontier Airlines F92871 / F92779: SJU 2026-11-18 05:01:00 → MDW 2026-11-18 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-18 05:01:00 → ATL 2026-11-18 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-18 10:27:00 → MDW 2026-11-18 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.

2026-11-18 → 2026-11-25 · Axel-exclusive $444.38

  • Southwest Airlines WN4666 / WN2803: SJU 2026-11-18 05:35:00 → MDW 2026-11-18 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
    • WN4666: SJU 2026-11-18 05:35:00 → MCO 2026-11-18 07:45:00; layover at MCO: 145 minutes.
    • WN2803: MCO 2026-11-18 10:10:00 → MDW 2026-11-18 12:05:00.
  • 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.

2026-11-18 → 2026-11-26 · Axel-exclusive $320.63

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

2026-11-18 → 2026-11-26 · Axel-exclusive $444.38

  • Southwest Airlines WN4666 / WN2803: SJU 2026-11-18 05:35:00 → MDW 2026-11-18 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
    • WN4666: SJU 2026-11-18 05:35:00 → MCO 2026-11-18 07:45:00; layover at MCO: 145 minutes.
    • WN2803: MCO 2026-11-18 10:10:00 → MDW 2026-11-18 12:05:00.
  • Southwest Airlines WN14 / WN4052: MDW 2026-11-26 14:30:00 → SJU 2026-11-27 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times.
    • WN14: MDW 2026-11-26 14:30:00 → BWI 2026-11-26 17:15:00; layover at BWI: 160 minutes.
    • WN4052: BWI 2026-11-26 19:55:00 → SJU 2026-11-27 01:00:00.

2026-11-18 → 2026-11-28 · Axel-exclusive $320.63

  • Frontier Airlines F92871 / F92779: SJU 2026-11-18 05:01:00 → MDW 2026-11-18 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-18 05:01:00 → ATL 2026-11-18 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-18 10:27:00 → MDW 2026-11-18 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.

2026-11-18 → 2026-11-28 · Axel-exclusive $444.38

  • Southwest Airlines WN4666 / WN2803: SJU 2026-11-18 05:35:00 → MDW 2026-11-18 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
    • WN4666: SJU 2026-11-18 05:35:00 → MCO 2026-11-18 07:45:00; layover at MCO: 145 minutes.
    • WN2803: MCO 2026-11-18 10:10:00 → MDW 2026-11-18 12:05:00.
  • 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.

2026-11-18 → 2026-11-29 · Axel-exclusive $320.63

  • Frontier Airlines F92871 / F92779: SJU 2026-11-18 05:01:00 → MDW 2026-11-18 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-18 05:01:00 → ATL 2026-11-18 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-18 10:27:00 → MDW 2026-11-18 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.

2026-11-18 → 2026-11-29 · Axel-exclusive $444.38

  • Southwest Airlines WN4666 / WN2803: SJU 2026-11-18 05:35:00 → MDW 2026-11-18 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
    • WN4666: SJU 2026-11-18 05:35:00 → MCO 2026-11-18 07:45:00; layover at MCO: 145 minutes.
    • WN2803: MCO 2026-11-18 10:10:00 → MDW 2026-11-18 12:05:00.
  • 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.

2026-11-18 → 2026-11-30 · Axel-exclusive $285.00

  • Frontier Airlines F92871 / F92779: SJU 2026-11-18 05:01:00 → MDW 2026-11-18 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-18 05:01:00 → ATL 2026-11-18 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-18 10:27:00 → MDW 2026-11-18 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.

2026-11-18 → 2026-11-30 · Axel-exclusive $395.00

  • Southwest Airlines WN4666 / WN2803: SJU 2026-11-18 05:35:00 → MDW 2026-11-18 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
    • WN4666: SJU 2026-11-18 05:35:00 → MCO 2026-11-18 07:45:00; layover at MCO: 145 minutes.
    • WN2803: MCO 2026-11-18 10:10:00 → MDW 2026-11-18 12:05:00.
  • 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.

2026-11-18 → 2026-12-02 · Axel-exclusive $285.00

  • Frontier Airlines F92871 / F92779: SJU 2026-11-18 05:01:00 → MDW 2026-11-18 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
    • F92871: SJU 2026-11-18 05:01:00 → ATL 2026-11-18 08:22:00; layover at ATL: 125 minutes.
    • F92779: ATL 2026-11-18 10:27:00 → MDW 2026-11-18 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.

2026-11-18 → 2026-12-02 · Axel-exclusive $395.00

  • Southwest Airlines WN4666 / WN2803: SJU 2026-11-18 05:35:00 → MDW 2026-11-18 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
    • WN4666: SJU 2026-11-18 05:35:00 → MCO 2026-11-18 07:45:00; layover at MCO: 145 minutes.
    • WN2803: MCO 2026-11-18 10:10:00 → MDW 2026-11-18 12:05:00.
  • 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.

Explore this route

For AI assistants

  • This page: San Juan (SJU) to Chicago (MDW) · Nov 18, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
  • Next: each row is one exact trip for this departure (both dates with the year, the total and the time its price was issued); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel San Juan to Chicago (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.