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Route overview: Jacksonville to Chicago (MDW) flight deals

Jacksonville → Chicago

Jun 26, 2027 · choose your return date

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.

June 2027

Jun 26, 2027 · One wayFrontier AirlinesUp to 1 stop each way$120.00 Jun 26, 2027 · One waySouthwest AirlinesNonstop$180.00 Jun 26, 2027 – Jun 27, 2027 · 1 nightFrontier AirlinesUp to 1 stop each way$225.00 Jun 26, 2027 – Jun 27, 2027 · 1 nightSouthwest AirlinesUp to 1 stop each way$330.00 Jun 26, 2027 – Jun 28, 2027 · 2 nightsFrontier AirlinesUp to 1 stop each way$225.00 Jun 26, 2027 – Jun 28, 2027 · 2 nightsSouthwest AirlinesNonstop$340.00 Jun 26, 2027 – Jun 29, 2027 · 3 nightsFrontier AirlinesUp to 1 stop each way$225.00 Jun 26, 2027 – Jun 29, 2027 · 3 nightsSouthwest AirlinesNonstop$340.00 Jun 26, 2027 – Jun 30, 2027 · 4 nightsFrontier AirlinesUp to 1 stop each way$225.00 Jun 26, 2027 – Jun 30, 2027 · 4 nightsSouthwest AirlinesNonstop$340.00 Jun 26, 2027 – Jul 1, 2027 · 5 nightsFrontier AirlinesUp to 1 stop each way$247.50 Jun 26, 2027 – Jul 1, 2027 · 5 nightsSouthwest AirlinesNonstop$374.00 Jun 26, 2027 – Jul 2, 2027 · 6 nightsFrontier AirlinesUp to 1 stop each way$247.50 Jun 26, 2027 – Jul 2, 2027 · 6 nightsSouthwest AirlinesNonstop$374.00 Jun 26, 2027 – Jul 3, 2027 · 7 nightsFrontier AirlinesUp to 1 stop each way$247.50 Jun 26, 2027 – Jul 3, 2027 · 7 nightsSouthwest AirlinesNonstop$374.00 Jun 26, 2027 – Jul 4, 2027 · 8 nightsFrontier AirlinesUp to 1 stop each way$247.50 Jun 26, 2027 – Jul 4, 2027 · 8 nightsSouthwest AirlinesUp to 1 stop each way$362.00 Jun 26, 2027 – Jul 5, 2027 · 9 nightsFrontier AirlinesUp to 1 stop each way$247.50 Jun 26, 2027 – Jul 5, 2027 · 9 nightsSouthwest AirlinesNonstop$374.00 Jun 26, 2027 – Jul 6, 2027 · 10 nightsFrontier AirlinesUp to 1 stop each way$247.50 Jun 26, 2027 – Jul 6, 2027 · 10 nightsSouthwest AirlinesNonstop$374.00 Jun 26, 2027 – Jul 7, 2027 · 11 nightsFrontier AirlinesUp to 1 stop each way$225.00 Jun 26, 2027 – Jul 7, 2027 · 11 nightsSouthwest AirlinesNonstop$340.00 Jun 26, 2027 – Jul 8, 2027 · 12 nightsFrontier AirlinesUp to 1 stop each way$225.00 Jun 26, 2027 – Jul 8, 2027 · 12 nightsSouthwest AirlinesNonstop$340.00 Jun 26, 2027 – Jul 9, 2027 · 13 nightsFrontier AirlinesUp to 1 stop each way$225.00 Jun 26, 2027 – Jul 9, 2027 · 13 nightsSouthwest AirlinesNonstop$340.00 Jun 26, 2027 – Jul 10, 2027 · 14 nightsFrontier AirlinesUp to 1 stop each way$225.00 Jun 26, 2027 – Jul 10, 2027 · 14 nightsSouthwest AirlinesNonstop$340.00

Flights for your trip

  1. Sat, Jun 26 · One way

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

    One-way total · 1 adult · Taxes included

  2. Sat, Jun 26 · One way

    Southwest Airlines
    6:50 pmJAX
    2h 30m
    Nonstop
    8:20 pmMDW

    One-way total · 1 adult · Taxes included

  3. Sat, Jun 26 – Sun, Jun 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

  4. Sat, Jun 26 – Sun, Jun 27

    Southwest Airlines
    6:50 pmJAX
    2h 30m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    2:30 pmMDW
    5h 5m
    BWI · 1h 5m
    8:35 pmJAX

    Round-trip total · 1 adult · Taxes included

  5. Sat, Jun 26 – Mon, Jun 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

  6. Sat, Jun 26 – Mon, Jun 28

    Southwest Airlines
    6:50 pmJAX
    2h 30m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    7:00 pmMDW
    2h 15m
    Nonstop
    10:15 pmJAX

    Round-trip total · 1 adult · Taxes included

  7. Sat, Jun 26 – Tue, Jun 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

  8. Sat, Jun 26 – Tue, Jun 29

    Southwest Airlines
    6:50 pmJAX
    2h 30m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    7:00 pmMDW
    2h 15m
    Nonstop
    10:15 pmJAX

    Round-trip total · 1 adult · Taxes included

  9. Sat, Jun 26 – Wed, Jun 30

    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

  10. Sat, Jun 26 – Wed, Jun 30

    Southwest Airlines
    6:50 pmJAX
    2h 30m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    7:00 pmMDW
    2h 15m
    Nonstop
    10:15 pmJAX

    Round-trip total · 1 adult · Taxes included

  11. Sat, Jun 26 – Fri, Jul 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

  12. Sat, Jun 26 – Fri, Jul 2

    Southwest Airlines
    6:50 pmJAX
    2h 30m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    8:00 amMDW
    2h 25m
    Nonstop
    11:25 amJAX

    Round-trip total · 1 adult · Taxes included

  13. Sat, Jun 26 – Sat, Jul 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

  14. Sat, Jun 26 – Sat, Jul 3

    Southwest Airlines
    6:50 pmJAX
    2h 30m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    7:00 pmMDW
    2h 15m
    Nonstop
    10:15 pmJAX

    Round-trip total · 1 adult · Taxes included

  15. Sat, Jun 26 – Sun, Jul 4

    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

  16. Sat, Jun 26 – Sun, Jul 4

    Southwest Airlines
    6:50 pmJAX
    2h 30m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    2:30 pmMDW
    5h 5m
    BWI · 1h 5m
    8:35 pmJAX

    Round-trip total · 1 adult · Taxes included

  17. Sat, Jun 26 – Tue, Jul 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

  18. Sat, Jun 26 – Tue, Jul 6

    Southwest Airlines
    6:50 pmJAX
    2h 30m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    7:00 pmMDW
    2h 15m
    Nonstop
    10:15 pmJAX

    Round-trip total · 1 adult · Taxes included

  19. Sat, Jun 26 – Wed, Jul 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

  20. Sat, Jun 26 – Wed, Jul 7

    Southwest Airlines
    6:50 pmJAX
    2h 30m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    7:00 pmMDW
    2h 15m
    Nonstop
    10:15 pmJAX

    Round-trip total · 1 adult · Taxes included

  21. Sat, Jun 26 – Thu, Jul 8

    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

  22. Sat, Jun 26 – Thu, Jul 8

    Southwest Airlines
    6:50 pmJAX
    2h 30m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    12:50 pmMDW
    2h 15m
    Nonstop
    4:05 pmJAX

    Round-trip total · 1 adult · Taxes included

  23. Sat, Jun 26 – Sat, Jul 10

    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

  24. Sat, Jun 26 – Sat, Jul 10

    Southwest Airlines
    6:50 pmJAX
    2h 30m
    Nonstop
    8:20 pmMDW
    Southwest Airlines
    7:00 pmMDW
    2h 15m
    Nonstop
    10:15 pmJAX

    Round-trip total · 1 adult · Taxes included

Swipe to see 23 more recent deals.

1 of 24

Make this trip yours

JAX ⇄ MDW

Economy

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Explore this route

All dates for this routeJun 25, 2027 · Return optionsJun 27, 2027 · 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)
2027-06-26 · one waySouthwest AirlinesWN2264Axel-exclusive $180.002026-10-29T01:16:41Z
2027-06-26 · one wayFrontier AirlinesF91549 + F92291Axel-exclusive $120.002026-10-29T01:16:41Z
2027-06-26 → 2027-06-27Frontier AirlinesF91549 + F92291 / F92144 + F91550Axel-exclusive $225.002026-10-29T01:16:41Z
2027-06-26 → 2027-06-27Southwest AirlinesWN2264 / WN14 + WN1041Axel-exclusive $330.002026-10-29T01:16:41Z
2027-06-26 → 2027-06-28Southwest AirlinesWN2264 / WN2946Axel-exclusive $340.002026-10-29T01:16:41Z
2027-06-26 → 2027-06-28Frontier AirlinesF91549 + F92291 / F92144 + F91550Axel-exclusive $225.002026-10-29T01:16:41Z
2027-06-26 → 2027-06-29Southwest AirlinesWN2264 / WN2946Axel-exclusive $340.002026-10-29T01:16:41Z
2027-06-26 → 2027-06-29Frontier AirlinesF91549 + F92291 / F92144 + F91550Axel-exclusive $225.002026-10-29T01:16:41Z
2027-06-26 → 2027-06-30Southwest AirlinesWN2264 / WN2946Axel-exclusive $340.002026-10-29T01:16:41Z
2027-06-26 → 2027-06-30Frontier AirlinesF91549 + F92291 / F92144 + F91550Axel-exclusive $225.002026-10-29T01:16:41Z
2027-06-26 → 2027-07-01Southwest AirlinesWN2264 / WN2041Axel-exclusive $374.002026-10-29T01:16:41Z
2027-06-26 → 2027-07-01Frontier AirlinesF91549 + F92291 / F92144 + F91550Axel-exclusive $247.502026-10-29T01:16:41Z
2027-06-26 → 2027-07-02Southwest AirlinesWN2264 / WN2262Axel-exclusive $374.002026-10-29T01:16:41Z
2027-06-26 → 2027-07-02Frontier AirlinesF91549 + F92291 / F92144 + F91550Axel-exclusive $247.502026-10-29T01:16:41Z
2027-06-26 → 2027-07-03Southwest AirlinesWN2264 / WN2946Axel-exclusive $374.002026-10-29T01:16:41Z
2027-06-26 → 2027-07-03Frontier AirlinesF91549 + F92291 / F92144 + F91550Axel-exclusive $247.502026-10-29T01:16:41Z
2027-06-26 → 2027-07-04Frontier AirlinesF91549 + F92291 / F92144 + F91550Axel-exclusive $247.502026-10-29T01:16:41Z
2027-06-26 → 2027-07-04Southwest AirlinesWN2264 / WN14 + WN1041Axel-exclusive $362.002026-10-29T01:16:41Z
2027-06-26 → 2027-07-05Southwest AirlinesWN2264 / WN2946Axel-exclusive $374.002026-10-29T01:16:41Z
2027-06-26 → 2027-07-05Frontier AirlinesF91549 + F92291 / F92144 + F91550Axel-exclusive $247.502026-10-29T01:16:41Z
2027-06-26 → 2027-07-06Southwest AirlinesWN2264 / WN2946Axel-exclusive $374.002026-10-29T01:16:41Z
2027-06-26 → 2027-07-06Frontier AirlinesF91549 + F92291 / F92144 + F91550Axel-exclusive $247.502026-10-29T01:16:41Z
2027-06-26 → 2027-07-07Southwest AirlinesWN2264 / WN2946Axel-exclusive $340.002026-10-29T01:16:41Z
2027-06-26 → 2027-07-07Frontier AirlinesF91549 + F92291 / F92144 + F91550Axel-exclusive $225.002026-10-29T01:16:41Z
2027-06-26 → 2027-07-08Southwest AirlinesWN2264 / WN2041Axel-exclusive $340.002026-10-29T01:16:41Z
2027-06-26 → 2027-07-08Frontier AirlinesF91549 + F92291 / F92144 + F91550Axel-exclusive $225.002026-10-29T01:16:41Z
2027-06-26 → 2027-07-09Southwest AirlinesWN2264 / WN2262Axel-exclusive $340.002026-10-29T01:16:41Z
2027-06-26 → 2027-07-09Frontier AirlinesF91549 + F92291 / F92144 + F91550Axel-exclusive $225.002026-10-29T01:16:41Z
2027-06-26 → 2027-07-10Southwest AirlinesWN2264 / WN2946Axel-exclusive $340.002026-10-29T01:16:41Z
2027-06-26 → 2027-07-10Frontier AirlinesF91549 + F92291 / F92144 + F91550Axel-exclusive $225.002026-10-29T01:16:41Z

Route overview: Jacksonville to Chicago (MDW) flight deals

2027-06-26 · one way · Axel-exclusive $120.00

  • Frontier Airlines F91549 / F92291: JAX 2027-06-26 19:03:00 → MDW 2027-06-26 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-06-26 19:03:00 → ATL 2027-06-26 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-06-26 22:48:00 → MDW 2027-06-26 23:47:00.

2027-06-26 · one way · Axel-exclusive $180.00

  • Southwest Airlines WN2264: JAX 2027-06-26 18:50:00 → MDW 2027-06-26 20:20:00; nonstop; 150 minutes. Local airport times.

2027-06-26 → 2027-06-27 · Axel-exclusive $225.00

  • Frontier Airlines F91549 / F92291: JAX 2027-06-26 19:03:00 → MDW 2027-06-26 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-06-26 19:03:00 → ATL 2027-06-26 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-06-26 22:48:00 → MDW 2027-06-26 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2027-06-27 13:11:00 → JAX 2027-06-27 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-06-27 13:11:00 → ATL 2027-06-27 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-06-27 18:09:00 → JAX 2027-06-27 19:25:00.

2027-06-26 → 2027-06-27 · Axel-exclusive $330.00

  • Southwest Airlines WN2264: JAX 2027-06-26 18:50:00 → MDW 2027-06-26 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN14 / WN1041: MDW 2027-06-27 14:30:00 → JAX 2027-06-27 20:35:00; 1 stop(s) via BWI; 305 minutes. Local airport times.
    • WN14: MDW 2027-06-27 14:30:00 → BWI 2027-06-27 17:15:00; layover at BWI: 65 minutes.
    • WN1041: BWI 2027-06-27 18:20:00 → JAX 2027-06-27 20:35:00.

2027-06-26 → 2027-06-28 · Axel-exclusive $225.00

  • Frontier Airlines F91549 / F92291: JAX 2027-06-26 19:03:00 → MDW 2027-06-26 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-06-26 19:03:00 → ATL 2027-06-26 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-06-26 22:48:00 → MDW 2027-06-26 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2027-06-28 13:11:00 → JAX 2027-06-28 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-06-28 13:11:00 → ATL 2027-06-28 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-06-28 18:09:00 → JAX 2027-06-28 19:25:00.

2027-06-26 → 2027-06-28 · Axel-exclusive $340.00

  • Southwest Airlines WN2264: JAX 2027-06-26 18:50:00 → MDW 2027-06-26 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2946: MDW 2027-06-28 19:00:00 → JAX 2027-06-28 22:15:00; nonstop; 135 minutes. Local airport times.

2027-06-26 → 2027-06-29 · Axel-exclusive $225.00

  • Frontier Airlines F91549 / F92291: JAX 2027-06-26 19:03:00 → MDW 2027-06-26 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-06-26 19:03:00 → ATL 2027-06-26 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-06-26 22:48:00 → MDW 2027-06-26 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2027-06-29 13:11:00 → JAX 2027-06-29 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-06-29 13:11:00 → ATL 2027-06-29 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-06-29 18:09:00 → JAX 2027-06-29 19:25:00.

2027-06-26 → 2027-06-29 · Axel-exclusive $340.00

  • Southwest Airlines WN2264: JAX 2027-06-26 18:50:00 → MDW 2027-06-26 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2946: MDW 2027-06-29 19:00:00 → JAX 2027-06-29 22:15:00; nonstop; 135 minutes. Local airport times.

2027-06-26 → 2027-06-30 · Axel-exclusive $225.00

  • Frontier Airlines F91549 / F92291: JAX 2027-06-26 19:03:00 → MDW 2027-06-26 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-06-26 19:03:00 → ATL 2027-06-26 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-06-26 22:48:00 → MDW 2027-06-26 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2027-06-30 13:11:00 → JAX 2027-06-30 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-06-30 13:11:00 → ATL 2027-06-30 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-06-30 18:09:00 → JAX 2027-06-30 19:25:00.

2027-06-26 → 2027-06-30 · Axel-exclusive $340.00

  • Southwest Airlines WN2264: JAX 2027-06-26 18:50:00 → MDW 2027-06-26 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2946: MDW 2027-06-30 19:00:00 → JAX 2027-06-30 22:15:00; nonstop; 135 minutes. Local airport times.

2027-06-26 → 2027-07-02 · Axel-exclusive $247.50

  • Frontier Airlines F91549 / F92291: JAX 2027-06-26 19:03:00 → MDW 2027-06-26 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-06-26 19:03:00 → ATL 2027-06-26 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-06-26 22:48:00 → MDW 2027-06-26 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2027-07-02 13:11:00 → JAX 2027-07-02 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-07-02 13:11:00 → ATL 2027-07-02 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-07-02 18:09:00 → JAX 2027-07-02 19:25:00.

2027-06-26 → 2027-07-02 · Axel-exclusive $374.00

  • Southwest Airlines WN2264: JAX 2027-06-26 18:50:00 → MDW 2027-06-26 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2262: MDW 2027-07-02 08:00:00 → JAX 2027-07-02 11:25:00; nonstop; 145 minutes. Local airport times.

2027-06-26 → 2027-07-03 · Axel-exclusive $247.50

  • Frontier Airlines F91549 / F92291: JAX 2027-06-26 19:03:00 → MDW 2027-06-26 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-06-26 19:03:00 → ATL 2027-06-26 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-06-26 22:48:00 → MDW 2027-06-26 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2027-07-03 13:11:00 → JAX 2027-07-03 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-07-03 13:11:00 → ATL 2027-07-03 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-07-03 18:09:00 → JAX 2027-07-03 19:25:00.

2027-06-26 → 2027-07-03 · Axel-exclusive $374.00

  • Southwest Airlines WN2264: JAX 2027-06-26 18:50:00 → MDW 2027-06-26 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2946: MDW 2027-07-03 19:00:00 → JAX 2027-07-03 22:15:00; nonstop; 135 minutes. Local airport times.

2027-06-26 → 2027-07-04 · Axel-exclusive $247.50

  • Frontier Airlines F91549 / F92291: JAX 2027-06-26 19:03:00 → MDW 2027-06-26 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-06-26 19:03:00 → ATL 2027-06-26 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-06-26 22:48:00 → MDW 2027-06-26 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2027-07-04 13:11:00 → JAX 2027-07-04 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-07-04 13:11:00 → ATL 2027-07-04 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-07-04 18:09:00 → JAX 2027-07-04 19:25:00.

2027-06-26 → 2027-07-04 · Axel-exclusive $362.00

  • Southwest Airlines WN2264: JAX 2027-06-26 18:50:00 → MDW 2027-06-26 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN14 / WN1041: MDW 2027-07-04 14:30:00 → JAX 2027-07-04 20:35:00; 1 stop(s) via BWI; 305 minutes. Local airport times.
    • WN14: MDW 2027-07-04 14:30:00 → BWI 2027-07-04 17:15:00; layover at BWI: 65 minutes.
    • WN1041: BWI 2027-07-04 18:20:00 → JAX 2027-07-04 20:35:00.

2027-06-26 → 2027-07-06 · Axel-exclusive $247.50

  • Frontier Airlines F91549 / F92291: JAX 2027-06-26 19:03:00 → MDW 2027-06-26 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-06-26 19:03:00 → ATL 2027-06-26 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-06-26 22:48:00 → MDW 2027-06-26 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2027-07-06 13:11:00 → JAX 2027-07-06 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-07-06 13:11:00 → ATL 2027-07-06 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-07-06 18:09:00 → JAX 2027-07-06 19:25:00.

2027-06-26 → 2027-07-06 · Axel-exclusive $374.00

  • Southwest Airlines WN2264: JAX 2027-06-26 18:50:00 → MDW 2027-06-26 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2946: MDW 2027-07-06 19:00:00 → JAX 2027-07-06 22:15:00; nonstop; 135 minutes. Local airport times.

2027-06-26 → 2027-07-07 · Axel-exclusive $225.00

  • Frontier Airlines F91549 / F92291: JAX 2027-06-26 19:03:00 → MDW 2027-06-26 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-06-26 19:03:00 → ATL 2027-06-26 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-06-26 22:48:00 → MDW 2027-06-26 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2027-07-07 13:11:00 → JAX 2027-07-07 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-07-07 13:11:00 → ATL 2027-07-07 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-07-07 18:09:00 → JAX 2027-07-07 19:25:00.

2027-06-26 → 2027-07-07 · Axel-exclusive $340.00

  • Southwest Airlines WN2264: JAX 2027-06-26 18:50:00 → MDW 2027-06-26 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2946: MDW 2027-07-07 19:00:00 → JAX 2027-07-07 22:15:00; nonstop; 135 minutes. Local airport times.

2027-06-26 → 2027-07-08 · Axel-exclusive $225.00

  • Frontier Airlines F91549 / F92291: JAX 2027-06-26 19:03:00 → MDW 2027-06-26 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-06-26 19:03:00 → ATL 2027-06-26 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-06-26 22:48:00 → MDW 2027-06-26 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2027-07-08 13:11:00 → JAX 2027-07-08 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-07-08 13:11:00 → ATL 2027-07-08 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-07-08 18:09:00 → JAX 2027-07-08 19:25:00.

2027-06-26 → 2027-07-08 · Axel-exclusive $340.00

  • Southwest Airlines WN2264: JAX 2027-06-26 18:50:00 → MDW 2027-06-26 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2041: MDW 2027-07-08 12:50:00 → JAX 2027-07-08 16:05:00; nonstop; 135 minutes. Local airport times.

2027-06-26 → 2027-07-10 · Axel-exclusive $225.00

  • Frontier Airlines F91549 / F92291: JAX 2027-06-26 19:03:00 → MDW 2027-06-26 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-06-26 19:03:00 → ATL 2027-06-26 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-06-26 22:48:00 → MDW 2027-06-26 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2027-07-10 13:11:00 → JAX 2027-07-10 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-07-10 13:11:00 → ATL 2027-07-10 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-07-10 18:09:00 → JAX 2027-07-10 19:25:00.

2027-06-26 → 2027-07-10 · Axel-exclusive $340.00

  • Southwest Airlines WN2264: JAX 2027-06-26 18:50:00 → MDW 2027-06-26 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2946: MDW 2027-07-10 19:00:00 → JAX 2027-07-10 22:15:00; nonstop; 135 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Jacksonville (JAX) to Chicago (MDW) · Jun 26, 2027 · 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 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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.