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Route overview: Jacksonville to Chicago (MDW) flight deals

Jacksonville (JAX) to Chicago (MDW), Nov 25, 2026: round trips from $217, one way from $135

Jacksonville (JAX) to Chicago (MDW), Nov 25, 2026: round trips from $217, one way from $135 on Axel, checked Oct 29, 2026. Lowest published fares: $217 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 25, 2026 – Dec 1, 2026; $135 one way, Axel-exclusive, Frontier Airlines, 1 stop, Nov 25, 2026; 1 adult, economy, checked Oct 29, 2026.

JAX → 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 25 · One way

    Frontier Airlines
    7:03 pmJAX
    5h 44m
    ATL · 2h 17m
    11:47 pmMDW

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  2. Wed, Nov 25 · One way

    Southwest Airlines
    6:55 pmJAX
    2h 25m
    Nonstop
    8:20 pmMDW

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  3. Wed, Nov 25 – Thu, Nov 26

    Frontier Airlines
    7:03 pmJAX
    5h 44m
    ATL · 2h 17m
    11:47 pmMDW
    Frontier Airlines
    1:11 pmMDW
    5h 14m
    ATL · 1h 51m
    7:25 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  4. Wed, Nov 25 – Thu, Nov 26

    Southwest Airlines
    6:55 pmJAX
    2h 25m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    12:50 pmMDW
    2h 15m
    Nonstop
    4:05 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  5. Wed, Nov 25 – Fri, Nov 27

    Frontier Airlines
    7:03 pmJAX
    5h 44m
    ATL · 2h 17m
    11:47 pmMDW
    Frontier Airlines
    1:11 pmMDW
    5h 14m
    ATL · 1h 51m
    7:25 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  6. Wed, Nov 25 – Fri, Nov 27

    Southwest Airlines
    6:55 pmJAX
    2h 25m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    8:00 amMDW
    2h 25m
    Nonstop
    11:25 amJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  7. Wed, Nov 25 – Sat, Nov 28

    Frontier Airlines
    7:03 pmJAX
    5h 44m
    ATL · 2h 17m
    11:47 pmMDW
    Frontier Airlines
    1:11 pmMDW
    5h 14m
    ATL · 1h 51m
    7:25 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  8. Wed, Nov 25 – Sat, Nov 28

    Southwest Airlines
    6:55 pmJAX
    2h 25m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    6:40 pmMDW
    2h 30m
    Nonstop
    10:10 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  9. Wed, Nov 25 – Sun, Nov 29

    Frontier Airlines
    7:03 pmJAX
    5h 44m
    ATL · 2h 17m
    11:47 pmMDW
    Frontier Airlines
    1:11 pmMDW
    5h 14m
    ATL · 1h 51m
    7:25 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  10. Wed, Nov 25 – Sun, Nov 29

    Southwest Airlines
    6:55 pmJAX
    2h 25m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    1:40 pmMDW
    6h 35m
    STL · 3h 20m
    9:15 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  11. Wed, Nov 25 – Tue, Dec 1

    Frontier Airlines
    7:03 pmJAX
    5h 44m
    ATL · 2h 17m
    11:47 pmMDW
    Frontier Airlines
    1:11 pmMDW
    5h 14m
    ATL · 1h 51m
    7:25 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  12. Wed, Nov 25 – Tue, Dec 1

    Southwest Airlines
    6:55 pmJAX
    2h 25m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    6:40 pmMDW
    2h 30m
    Nonstop
    10:10 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  13. Wed, Nov 25 – Wed, Dec 2

    Frontier Airlines
    7:03 pmJAX
    5h 44m
    ATL · 2h 17m
    11:47 pmMDW
    Frontier Airlines
    1:11 pmMDW
    5h 14m
    ATL · 1h 51m
    7:25 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  14. Wed, Nov 25 – Wed, Dec 2

    Southwest Airlines
    6:55 pmJAX
    2h 25m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    6:40 pmMDW
    2h 30m
    Nonstop
    10:10 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  15. Wed, Nov 25 – Thu, Dec 3

    Frontier Airlines
    7:03 pmJAX
    5h 44m
    ATL · 2h 17m
    11:47 pmMDW
    Frontier Airlines
    1:11 pmMDW
    5h 14m
    ATL · 1h 51m
    7:25 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  16. Wed, Nov 25 – Thu, Dec 3

    Southwest Airlines
    6:55 pmJAX
    2h 25m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    12:50 pmMDW
    2h 15m
    Nonstop
    4:05 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  17. Wed, Nov 25 – Sat, Dec 5

    Frontier Airlines
    7:03 pmJAX
    5h 44m
    ATL · 2h 17m
    11:47 pmMDW
    Frontier Airlines
    1:11 pmMDW
    5h 14m
    ATL · 1h 51m
    7:25 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  18. Wed, Nov 25 – Sat, Dec 5

    Southwest Airlines
    6:55 pmJAX
    2h 25m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    6:40 pmMDW
    2h 30m
    Nonstop
    10:10 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  19. Wed, Nov 25 – Sun, Dec 6

    Frontier Airlines
    7:03 pmJAX
    5h 44m
    ATL · 2h 17m
    11:47 pmMDW
    Frontier Airlines
    1:11 pmMDW
    5h 14m
    ATL · 1h 51m
    7:25 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  20. Wed, Nov 25 – Sun, Dec 6

    Southwest Airlines
    6:55 pmJAX
    2h 25m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    1:40 pmMDW
    6h 35m
    STL · 3h 20m
    9:15 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  21. Wed, Nov 25 – Mon, Dec 7

    Frontier Airlines
    7:03 pmJAX
    5h 44m
    ATL · 2h 17m
    11:47 pmMDW
    Frontier Airlines
    1:11 pmMDW
    5h 14m
    ATL · 1h 51m
    7:25 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  22. Wed, Nov 25 – Mon, Dec 7

    Southwest Airlines
    6:55 pmJAX
    2h 25m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    6:40 pmMDW
    2h 30m
    Nonstop
    10:10 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  23. Wed, Nov 25 – Wed, Dec 9

    Frontier Airlines
    7:03 pmJAX
    5h 44m
    ATL · 2h 17m
    11:47 pmMDW
    Frontier Airlines
    1:11 pmMDW
    5h 14m
    ATL · 1h 51m
    7:25 pmJAX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  24. Wed, Nov 25 – Wed, Dec 9

    Southwest Airlines
    6:55 pmJAX
    2h 25m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    6:40 pmMDW
    2h 30m
    Nonstop
    10:10 pmJAX

    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

JAX ⇄ 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 24, 2026 · Return optionsNov 26, 2026 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

Jacksonville (JAX) to Chicago (MDW), Nov 25, 2026: round trips from $217, one way from $135 on Axel, checked Oct 29, 2026. Lowest published fares: $217 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 25, 2026 – Dec 1, 2026; $135 one way, Axel-exclusive, Frontier Airlines, 1 stop, Nov 25, 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)
2026-11-25 · one waySouthwest AirlinesWN226418:55:00→20:20:00 2h 25m nonstopAxel-exclusive $209.252026-10-29T01:16:41Z
2026-11-25 · one wayFrontier AirlinesF91549 + F9229119:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $135.002026-10-29T01:16:41Z
2026-11-25 → 2026-11-26Southwest AirlinesWN2264 / WN204118:55:00→20:20:00 2h 25m nonstop · 12:50:00→16:05:00 2h 15m nonstopAxel-exclusive $391.502026-10-29T01:16:41Z
2026-11-25 → 2026-11-26Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $249.762026-10-29T01:16:41Z
2026-11-25 → 2026-11-27Southwest AirlinesWN2264 / WN226218:55:00→20:20:00 2h 25m nonstop · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $391.502026-10-29T01:16:41Z
2026-11-25 → 2026-11-27Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $249.762026-10-29T01:16:41Z
2026-11-25 → 2026-11-28Southwest AirlinesWN2264 / WN217818:55:00→20:20:00 2h 25m nonstop · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $391.502026-10-29T01:16:41Z
2026-11-25 → 2026-11-28Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $249.762026-10-29T01:16:41Z
2026-11-25 → 2026-11-29Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $249.762026-10-29T01:16:41Z
2026-11-25 → 2026-11-29Southwest AirlinesWN2264 / WN3092 + WN480718:55:00→20:20:00 2h 25m nonstop · 13:40:00→21:15:00 6h 35m 1 stop via STLAxel-exclusive $381.382026-10-29T01:16:41Z
2026-11-25 → 2026-11-30Southwest AirlinesWN2264 / WN217818:55:00→20:20:00 2h 25m nonstop · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $391.502026-10-29T01:16:41Z
2026-11-25 → 2026-11-30Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $249.762026-10-29T01:16:41Z
2026-11-25 → 2026-12-01Southwest AirlinesWN2264 / WN217818:55:00→20:20:00 2h 25m nonstop · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $340.752026-10-29T01:16:41Z
2026-11-25 → 2026-12-01Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $217.382026-10-29T01:16:41Z
2026-11-25 → 2026-12-02Southwest AirlinesWN2264 / WN217818:55:00→20:20:00 2h 25m nonstop · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $340.752026-10-29T01:16:41Z
2026-11-25 → 2026-12-02Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $217.382026-10-29T01:16:41Z
2026-11-25 → 2026-12-03Southwest AirlinesWN2264 / WN204118:55:00→20:20:00 2h 25m nonstop · 12:50:00→16:05:00 2h 15m nonstopAxel-exclusive $340.752026-10-29T01:16:41Z
2026-11-25 → 2026-12-03Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $217.382026-10-29T01:16:41Z
2026-11-25 → 2026-12-04Southwest AirlinesWN2264 / WN226218:55:00→20:20:00 2h 25m nonstop · 08:00:00→11:25:00 2h 25m nonstopAxel-exclusive $340.752026-10-29T01:16:41Z
2026-11-25 → 2026-12-04Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $217.382026-10-29T01:16:41Z
2026-11-25 → 2026-12-05Southwest AirlinesWN2264 / WN217818:55:00→20:20:00 2h 25m nonstop · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $340.752026-10-29T01:16:41Z
2026-11-25 → 2026-12-05Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $217.382026-10-29T01:16:41Z
2026-11-25 → 2026-12-06Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $217.382026-10-29T01:16:41Z
2026-11-25 → 2026-12-06Southwest AirlinesWN2264 / WN3092 + WN480718:55:00→20:20:00 2h 25m nonstop · 13:40:00→21:15:00 6h 35m 1 stop via STLAxel-exclusive $333.252026-10-29T01:16:41Z
2026-11-25 → 2026-12-07Southwest AirlinesWN2264 / WN217818:55:00→20:20:00 2h 25m nonstop · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $340.752026-10-29T01:16:41Z
2026-11-25 → 2026-12-07Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $217.382026-10-29T01:16:41Z
2026-11-25 → 2026-12-08Southwest AirlinesWN2264 / WN217818:55:00→20:20:00 2h 25m nonstop · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $340.752026-10-29T01:16:41Z
2026-11-25 → 2026-12-08Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $217.382026-10-29T01:16:41Z
2026-11-25 → 2026-12-09Southwest AirlinesWN2264 / WN217818:55:00→20:20:00 2h 25m nonstop · 18:40:00→22:10:00 2h 30m nonstopAxel-exclusive $340.752026-10-29T01:16:41Z
2026-11-25 → 2026-12-09Frontier AirlinesF91549 + F92291 / F92144 + F9155019:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $217.382026-10-29T01:16:41Z

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: Jacksonville to Chicago (MDW) flight deals

2026-11-25 · one way · Axel-exclusive $135.00

  • Frontier Airlines F91549 / F92291: JAX 2026-11-25 19:03:00 → MDW 2026-11-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-25 19:03:00 → ATL 2026-11-25 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-25 22:48:00 → MDW 2026-11-25 23:47:00.

2026-11-25 · one way · Axel-exclusive $209.25

  • Southwest Airlines WN2264: JAX 2026-11-25 18:55:00 → MDW 2026-11-25 20:20:00; nonstop; 145 minutes. Local airport times.

2026-11-25 → 2026-11-26 · Axel-exclusive $249.76

  • Frontier Airlines F91549 / F92291: JAX 2026-11-25 19:03:00 → MDW 2026-11-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-25 19:03:00 → ATL 2026-11-25 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-25 22:48:00 → MDW 2026-11-25 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-11-26 13:11:00 → JAX 2026-11-26 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-11-26 13:11:00 → ATL 2026-11-26 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-11-26 18:09:00 → JAX 2026-11-26 19:25:00.

2026-11-25 → 2026-11-26 · Axel-exclusive $391.50

  • Southwest Airlines WN2264: JAX 2026-11-25 18:55:00 → MDW 2026-11-25 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2041: MDW 2026-11-26 12:50:00 → JAX 2026-11-26 16:05:00; nonstop; 135 minutes. Local airport times.

2026-11-25 → 2026-11-27 · Axel-exclusive $249.76

  • Frontier Airlines F91549 / F92291: JAX 2026-11-25 19:03:00 → MDW 2026-11-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-25 19:03:00 → ATL 2026-11-25 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-25 22:48:00 → MDW 2026-11-25 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-11-27 13:11:00 → JAX 2026-11-27 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-11-27 13:11:00 → ATL 2026-11-27 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-11-27 18:09:00 → JAX 2026-11-27 19:25:00.

2026-11-25 → 2026-11-27 · Axel-exclusive $391.50

  • Southwest Airlines WN2264: JAX 2026-11-25 18:55:00 → MDW 2026-11-25 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2262: MDW 2026-11-27 08:00:00 → JAX 2026-11-27 11:25:00; nonstop; 145 minutes. Local airport times.

2026-11-25 → 2026-11-28 · Axel-exclusive $249.76

  • Frontier Airlines F91549 / F92291: JAX 2026-11-25 19:03:00 → MDW 2026-11-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-25 19:03:00 → ATL 2026-11-25 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-25 22:48:00 → MDW 2026-11-25 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-11-28 13:11:00 → JAX 2026-11-28 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-11-28 13:11:00 → ATL 2026-11-28 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-11-28 18:09:00 → JAX 2026-11-28 19:25:00.

2026-11-25 → 2026-11-28 · Axel-exclusive $391.50

  • Southwest Airlines WN2264: JAX 2026-11-25 18:55:00 → MDW 2026-11-25 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2178: MDW 2026-11-28 18:40:00 → JAX 2026-11-28 22:10:00; nonstop; 150 minutes. Local airport times.

2026-11-25 → 2026-11-29 · Axel-exclusive $249.76

  • Frontier Airlines F91549 / F92291: JAX 2026-11-25 19:03:00 → MDW 2026-11-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-25 19:03:00 → ATL 2026-11-25 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-25 22:48:00 → MDW 2026-11-25 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-11-29 13:11:00 → JAX 2026-11-29 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-11-29 13:11:00 → ATL 2026-11-29 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-11-29 18:09:00 → JAX 2026-11-29 19:25:00.

2026-11-25 → 2026-11-29 · Axel-exclusive $381.38

  • Southwest Airlines WN2264: JAX 2026-11-25 18:55:00 → MDW 2026-11-25 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN3092 / WN4807: MDW 2026-11-29 13:40:00 → JAX 2026-11-29 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2026-11-29 13:40:00 → STL 2026-11-29 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2026-11-29 18:15:00 → JAX 2026-11-29 21:15:00.

2026-11-25 → 2026-12-01 · Axel-exclusive $217.38

  • Frontier Airlines F91549 / F92291: JAX 2026-11-25 19:03:00 → MDW 2026-11-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-25 19:03:00 → ATL 2026-11-25 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-25 22:48:00 → MDW 2026-11-25 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-01 13:11:00 → JAX 2026-12-01 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-01 13:11:00 → ATL 2026-12-01 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-01 18:09:00 → JAX 2026-12-01 19:25:00.

2026-11-25 → 2026-12-01 · Axel-exclusive $340.75

  • Southwest Airlines WN2264: JAX 2026-11-25 18:55:00 → MDW 2026-11-25 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2178: MDW 2026-12-01 18:40:00 → JAX 2026-12-01 22:10:00; nonstop; 150 minutes. Local airport times.

2026-11-25 → 2026-12-02 · Axel-exclusive $217.38

  • Frontier Airlines F91549 / F92291: JAX 2026-11-25 19:03:00 → MDW 2026-11-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-25 19:03:00 → ATL 2026-11-25 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-25 22:48:00 → MDW 2026-11-25 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-02 13:11:00 → JAX 2026-12-02 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-02 13:11:00 → ATL 2026-12-02 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-02 18:09:00 → JAX 2026-12-02 19:25:00.

2026-11-25 → 2026-12-02 · Axel-exclusive $340.75

  • Southwest Airlines WN2264: JAX 2026-11-25 18:55:00 → MDW 2026-11-25 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2178: MDW 2026-12-02 18:40:00 → JAX 2026-12-02 22:10:00; nonstop; 150 minutes. Local airport times.

2026-11-25 → 2026-12-03 · Axel-exclusive $217.38

  • Frontier Airlines F91549 / F92291: JAX 2026-11-25 19:03:00 → MDW 2026-11-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-25 19:03:00 → ATL 2026-11-25 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-25 22:48:00 → MDW 2026-11-25 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-03 13:11:00 → JAX 2026-12-03 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-03 13:11:00 → ATL 2026-12-03 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-03 18:09:00 → JAX 2026-12-03 19:25:00.

2026-11-25 → 2026-12-03 · Axel-exclusive $340.75

  • Southwest Airlines WN2264: JAX 2026-11-25 18:55:00 → MDW 2026-11-25 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2041: MDW 2026-12-03 12:50:00 → JAX 2026-12-03 16:05:00; nonstop; 135 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $217.38

  • Frontier Airlines F91549 / F92291: JAX 2026-11-25 19:03:00 → MDW 2026-11-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-25 19:03:00 → ATL 2026-11-25 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-25 22:48:00 → MDW 2026-11-25 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-05 13:11:00 → JAX 2026-12-05 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-05 13:11:00 → ATL 2026-12-05 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-05 18:09:00 → JAX 2026-12-05 19:25:00.

2026-11-25 → 2026-12-05 · Axel-exclusive $340.75

  • Southwest Airlines WN2264: JAX 2026-11-25 18:55:00 → MDW 2026-11-25 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2178: MDW 2026-12-05 18:40:00 → JAX 2026-12-05 22:10:00; nonstop; 150 minutes. Local airport times.

2026-11-25 → 2026-12-06 · Axel-exclusive $217.38

  • Frontier Airlines F91549 / F92291: JAX 2026-11-25 19:03:00 → MDW 2026-11-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-25 19:03:00 → ATL 2026-11-25 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-25 22:48:00 → MDW 2026-11-25 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-06 13:11:00 → JAX 2026-12-06 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-06 13:11:00 → ATL 2026-12-06 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-06 18:09:00 → JAX 2026-12-06 19:25:00.

2026-11-25 → 2026-12-06 · Axel-exclusive $333.25

  • Southwest Airlines WN2264: JAX 2026-11-25 18:55:00 → MDW 2026-11-25 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN3092 / WN4807: MDW 2026-12-06 13:40:00 → JAX 2026-12-06 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2026-12-06 13:40:00 → STL 2026-12-06 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2026-12-06 18:15:00 → JAX 2026-12-06 21:15:00.

2026-11-25 → 2026-12-07 · Axel-exclusive $217.38

  • Frontier Airlines F91549 / F92291: JAX 2026-11-25 19:03:00 → MDW 2026-11-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-25 19:03:00 → ATL 2026-11-25 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-25 22:48:00 → MDW 2026-11-25 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-07 13:11:00 → JAX 2026-12-07 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-07 13:11:00 → ATL 2026-12-07 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-07 18:09:00 → JAX 2026-12-07 19:25:00.

2026-11-25 → 2026-12-07 · Axel-exclusive $340.75

  • Southwest Airlines WN2264: JAX 2026-11-25 18:55:00 → MDW 2026-11-25 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2178: MDW 2026-12-07 18:40:00 → JAX 2026-12-07 22:10:00; nonstop; 150 minutes. Local airport times.

2026-11-25 → 2026-12-09 · Axel-exclusive $217.38

  • Frontier Airlines F91549 / F92291: JAX 2026-11-25 19:03:00 → MDW 2026-11-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-25 19:03:00 → ATL 2026-11-25 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-25 22:48:00 → MDW 2026-11-25 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-09 13:11:00 → JAX 2026-12-09 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-09 13:11:00 → ATL 2026-12-09 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-09 18:09:00 → JAX 2026-12-09 19:25:00.

2026-11-25 → 2026-12-09 · Axel-exclusive $340.75

  • Southwest Airlines WN2264: JAX 2026-11-25 18:55:00 → MDW 2026-11-25 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2178: MDW 2026-12-09 18:40:00 → JAX 2026-12-09 22:10:00; nonstop; 150 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Jacksonville (JAX) to Chicago (MDW) · Nov 25, 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 Jacksonville 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.