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Route overview: Chicago to Jacksonville (JAX) flight deals

Chicago (MDW) to Jacksonville (JAX), Jan 24, 2027: round trips from $190, one way from $100

Chicago (MDW) to Jacksonville (JAX), Jan 24, 2027: round trips from $190, one way from $100 on Axel, checked Oct 29, 2026. Lowest published fares: $190 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Jan 24–25, 2027; $100 one way, Axel-exclusive, Frontier Airlines, 1 stop, Jan 24, 2027; 1 adult, economy, checked Oct 29, 2026.

MDW → JAX1 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.

January 2027

Flights for your trip

  1. Sun, Jan 24 · One way

    Frontier Airlines
    1:11 pmMDW
    5h 14m
    ATL · 1h 51m
    7:25 pmJAX

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  2. Sun, Jan 24 · One way

    Southwest Airlines
    1:40 pmMDW
    6h 35m
    STL · 3h 20m
    9:15 pmJAX

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  3. Sun, Jan 24 – Mon, Jan 25

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  4. Sun, Jan 24 – Mon, Jan 25

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  5. Sun, Jan 24 – Tue, Jan 26

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  6. Sun, Jan 24 – Tue, Jan 26

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  7. Sun, Jan 24 – Wed, Jan 27

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  8. Sun, Jan 24 – Wed, Jan 27

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  9. Sun, Jan 24 – Thu, Jan 28

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  10. Sun, Jan 24 – Thu, Jan 28

    Southwest Airlines
    1:40 pmMDW
    6h 35m
    STL · 3h 20m
    9:15 pmJAX
    Southwest Airlines
    8:00 amJAX
    5h 15m
    BWI · 1h 15m
    12:15 pmMDW

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  11. Sun, Jan 24 – Sat, Jan 30

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  12. Sun, Jan 24 – Sat, Jan 30

    Southwest Airlines
    1:40 pmMDW
    6h 35m
    STL · 3h 20m
    9:15 pmJAX
    Southwest Airlines
    6:50 pmJAX
    2h 30m
    Nonstop
    8:20 pmMDW

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  13. Sun, Jan 24 – Sun, Jan 31

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  14. Sun, Jan 24 – Sun, Jan 31

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  15. Sun, Jan 24 – Mon, Feb 1

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  16. Sun, Jan 24 – Mon, Feb 1

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  17. Sun, Jan 24 – Wed, Feb 3

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  18. Sun, Jan 24 – Wed, Feb 3

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  19. Sun, Jan 24 – Thu, Feb 4

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  20. Sun, Jan 24 – Thu, Feb 4

    Southwest Airlines
    1:40 pmMDW
    6h 35m
    STL · 3h 20m
    9:15 pmJAX
    Southwest Airlines
    8:00 amJAX
    5h 15m
    BWI · 1h 15m
    12:15 pmMDW

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  21. Sun, Jan 24 – Fri, Feb 5

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  22. Sun, Jan 24 – Fri, Feb 5

    Southwest Airlines
    1:40 pmMDW
    6h 35m
    STL · 3h 20m
    9:15 pmJAX
    Southwest Airlines
    6:50 pmJAX
    2h 30m
    Nonstop
    8:20 pmMDW

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  23. Sun, Jan 24 – Sun, Feb 7

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  24. Sun, Jan 24 – Sun, Feb 7

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

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

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MDW ⇄ JAX

Economy

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Explore this route

All dates for this routeJan 23, 2027 · Return optionsJan 25, 2027 · Return optionsHotels in Amelia Island with Axel
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Chicago (MDW) to Jacksonville (JAX), Jan 24, 2027: round trips from $190, one way from $100 on Axel, checked Oct 29, 2026. Lowest published fares: $190 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Jan 24–25, 2027; $100 one way, Axel-exclusive, Frontier Airlines, 1 stop, Jan 24, 2027; 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)
2027-01-24 · one wayFrontier AirlinesF92144 + F9155013:11:00→19:25:00 5h 14m 1 stop via ATLAxel-exclusive $99.752026-10-29T01:29:09Z
2027-01-24 · one waySouthwest AirlinesWN3092 + WN480713:40:00→21:15:00 6h 35m 1 stop via STLAxel-exclusive $152.002026-10-29T01:29:09Z
2027-01-24 → 2027-01-25Frontier AirlinesF92144 + F91550 / F91549 + F9229113:11:00→19:25:00 5h 14m 1 stop via ATL · 19:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $190.002026-10-29T01:29:09Z
2027-01-24 → 2027-01-25Southwest AirlinesWN3092 + WN4807 / WN226413:40:00→21:15:00 6h 35m 1 stop via STL · 18:55:00→20:20:00 2h 25m nonstopAxel-exclusive $280.252026-10-29T01:29:09Z
2027-01-24 → 2027-01-26Frontier AirlinesF92144 + F91550 / F91549 + F9229113:11:00→19:25:00 5h 14m 1 stop via ATL · 19:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $190.002026-10-29T01:29:09Z
2027-01-24 → 2027-01-26Southwest AirlinesWN3092 + WN4807 / WN226413:40:00→21:15:00 6h 35m 1 stop via STL · 18:55:00→20:20:00 2h 25m nonstopAxel-exclusive $280.252026-10-29T01:29:09Z
2027-01-24 → 2027-01-27Frontier AirlinesF92144 + F91550 / F91549 + F9229113:11:00→19:25:00 5h 14m 1 stop via ATL · 19:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $190.002026-10-29T01:29:09Z
2027-01-24 → 2027-01-27Southwest AirlinesWN3092 + WN4807 / WN226413:40:00→21:15:00 6h 35m 1 stop via STL · 18:55:00→20:20:00 2h 25m nonstopAxel-exclusive $280.252026-10-29T01:29:09Z
2027-01-24 → 2027-01-28Frontier AirlinesF92144 + F91550 / F91549 + F9229113:11:00→19:25:00 5h 14m 1 stop via ATL · 19:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $190.002026-10-29T01:29:09Z
2027-01-24 → 2027-01-28Southwest AirlinesWN3092 + WN4807 / WN2256 + WN107013:40:00→21:15:00 6h 35m 1 stop via STL · 08:00:00→12:15:00 5h 15m 1 stop via BWIAxel-exclusive $294.502026-10-29T01:29:09Z
2027-01-24 → 2027-01-29Frontier AirlinesF92144 + F91550 / F91549 + F9229113:11:00→19:25:00 5h 14m 1 stop via ATL · 19:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $190.002026-10-29T01:29:09Z
2027-01-24 → 2027-01-29Southwest AirlinesWN3092 + WN4807 / WN226413:40:00→21:15:00 6h 35m 1 stop via STL · 18:50:00→20:20:00 2h 30m nonstopAxel-exclusive $280.252026-10-29T01:29:09Z
2027-01-24 → 2027-01-30Frontier AirlinesF92144 + F91550 / F91549 + F9229113:11:00→19:25:00 5h 14m 1 stop via ATL · 19:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $190.002026-10-29T01:29:09Z
2027-01-24 → 2027-01-30Southwest AirlinesWN3092 + WN4807 / WN226413:40:00→21:15:00 6h 35m 1 stop via STL · 18:50:00→20:20:00 2h 30m nonstopAxel-exclusive $280.252026-10-29T01:29:09Z
2027-01-24 → 2027-01-31Frontier AirlinesF92144 + F91550 / F91549 + F9229113:11:00→19:25:00 5h 14m 1 stop via ATL · 19:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $190.002026-10-29T01:29:09Z
2027-01-24 → 2027-01-31Southwest AirlinesWN3092 + WN4807 / WN226413:40:00→21:15:00 6h 35m 1 stop via STL · 18:55:00→20:20:00 2h 25m nonstopAxel-exclusive $280.252026-10-29T01:29:09Z
2027-01-24 → 2027-02-01Frontier AirlinesF92144 + F91550 / F91549 + F9229113:11:00→19:25:00 5h 14m 1 stop via ATL · 19:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $195.002026-10-29T01:29:09Z
2027-01-24 → 2027-02-01Southwest AirlinesWN3092 + WN4807 / WN226413:40:00→21:15:00 6h 35m 1 stop via STL · 18:55:00→20:20:00 2h 25m nonstopAxel-exclusive $287.252026-10-29T01:29:09Z
2027-01-24 → 2027-02-02Frontier AirlinesF92144 + F91550 / F91549 + F9229113:11:00→19:25:00 5h 14m 1 stop via ATL · 19:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $195.002026-10-29T01:29:09Z
2027-01-24 → 2027-02-02Southwest AirlinesWN3092 + WN4807 / WN226413:40:00→21:15:00 6h 35m 1 stop via STL · 18:55:00→20:20:00 2h 25m nonstopAxel-exclusive $287.252026-10-29T01:29:09Z
2027-01-24 → 2027-02-03Frontier AirlinesF92144 + F91550 / F91549 + F9229113:11:00→19:25:00 5h 14m 1 stop via ATL · 19:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $195.002026-10-29T01:29:09Z
2027-01-24 → 2027-02-03Southwest AirlinesWN3092 + WN4807 / WN226413:40:00→21:15:00 6h 35m 1 stop via STL · 18:55:00→20:20:00 2h 25m nonstopAxel-exclusive $287.252026-10-29T01:29:09Z
2027-01-24 → 2027-02-04Frontier AirlinesF92144 + F91550 / F91549 + F9229113:11:00→19:25:00 5h 14m 1 stop via ATL · 19:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $195.002026-10-29T01:29:09Z
2027-01-24 → 2027-02-04Southwest AirlinesWN3092 + WN4807 / WN2256 + WN107013:40:00→21:15:00 6h 35m 1 stop via STL · 08:00:00→12:15:00 5h 15m 1 stop via BWIAxel-exclusive $302.252026-10-29T01:29:09Z
2027-01-24 → 2027-02-05Frontier AirlinesF92144 + F91550 / F91549 + F9229113:11:00→19:25:00 5h 14m 1 stop via ATL · 19:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $195.002026-10-29T01:29:09Z
2027-01-24 → 2027-02-05Southwest AirlinesWN3092 + WN4807 / WN226413:40:00→21:15:00 6h 35m 1 stop via STL · 18:50:00→20:20:00 2h 30m nonstopAxel-exclusive $287.252026-10-29T01:29:09Z
2027-01-24 → 2027-02-06Frontier AirlinesF92144 + F91550 / F91549 + F9229113:11:00→19:25:00 5h 14m 1 stop via ATL · 19:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $195.002026-10-29T01:29:09Z
2027-01-24 → 2027-02-06Southwest AirlinesWN3092 + WN4807 / WN226413:40:00→21:15:00 6h 35m 1 stop via STL · 18:50:00→20:20:00 2h 30m nonstopAxel-exclusive $287.252026-10-29T01:29:09Z
2027-01-24 → 2027-02-07Frontier AirlinesF92144 + F91550 / F91549 + F9229113:11:00→19:25:00 5h 14m 1 stop via ATL · 19:03:00→23:47:00 5h 44m 1 stop via ATLAxel-exclusive $195.002026-10-29T01:29:09Z
2027-01-24 → 2027-02-07Southwest AirlinesWN3092 + WN4807 / WN226413:40:00→21:15:00 6h 35m 1 stop via STL · 18:55:00→20:20:00 2h 25m nonstopAxel-exclusive $287.252026-10-29T01:29:09Z

Route overview: Chicago to Jacksonville (JAX) flight deals

2027-01-24 · one way · Axel-exclusive $99.75

  • Frontier Airlines F92144 / F91550: MDW 2027-01-24 13:11:00 → JAX 2027-01-24 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-01-24 13:11:00 → ATL 2027-01-24 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-01-24 18:09:00 → JAX 2027-01-24 19:25:00.

2027-01-24 · one way · Axel-exclusive $152.00

  • Southwest Airlines WN3092 / WN4807: MDW 2027-01-24 13:40:00 → JAX 2027-01-24 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2027-01-24 13:40:00 → STL 2027-01-24 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2027-01-24 18:15:00 → JAX 2027-01-24 21:15:00.

2027-01-24 → 2027-01-25 · Axel-exclusive $190.00

  • Frontier Airlines F92144 / F91550: MDW 2027-01-24 13:11:00 → JAX 2027-01-24 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-01-24 13:11:00 → ATL 2027-01-24 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-01-24 18:09:00 → JAX 2027-01-24 19:25:00.
  • Frontier Airlines F91549 / F92291: JAX 2027-01-25 19:03:00 → MDW 2027-01-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-01-25 19:03:00 → ATL 2027-01-25 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-01-25 22:48:00 → MDW 2027-01-25 23:47:00.

2027-01-24 → 2027-01-25 · Axel-exclusive $280.25

  • Southwest Airlines WN3092 / WN4807: MDW 2027-01-24 13:40:00 → JAX 2027-01-24 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2027-01-24 13:40:00 → STL 2027-01-24 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2027-01-24 18:15:00 → JAX 2027-01-24 21:15:00.
  • Southwest Airlines WN2264: JAX 2027-01-25 18:55:00 → MDW 2027-01-25 20:20:00; nonstop; 145 minutes. Local airport times.

2027-01-24 → 2027-01-26 · Axel-exclusive $190.00

  • Frontier Airlines F92144 / F91550: MDW 2027-01-24 13:11:00 → JAX 2027-01-24 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-01-24 13:11:00 → ATL 2027-01-24 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-01-24 18:09:00 → JAX 2027-01-24 19:25:00.
  • Frontier Airlines F91549 / F92291: JAX 2027-01-26 19:03:00 → MDW 2027-01-26 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-01-26 19:03:00 → ATL 2027-01-26 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-01-26 22:48:00 → MDW 2027-01-26 23:47:00.

2027-01-24 → 2027-01-26 · Axel-exclusive $280.25

  • Southwest Airlines WN3092 / WN4807: MDW 2027-01-24 13:40:00 → JAX 2027-01-24 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2027-01-24 13:40:00 → STL 2027-01-24 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2027-01-24 18:15:00 → JAX 2027-01-24 21:15:00.
  • Southwest Airlines WN2264: JAX 2027-01-26 18:55:00 → MDW 2027-01-26 20:20:00; nonstop; 145 minutes. Local airport times.

2027-01-24 → 2027-01-27 · Axel-exclusive $190.00

  • Frontier Airlines F92144 / F91550: MDW 2027-01-24 13:11:00 → JAX 2027-01-24 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-01-24 13:11:00 → ATL 2027-01-24 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-01-24 18:09:00 → JAX 2027-01-24 19:25:00.
  • Frontier Airlines F91549 / F92291: JAX 2027-01-27 19:03:00 → MDW 2027-01-27 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-01-27 19:03:00 → ATL 2027-01-27 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-01-27 22:48:00 → MDW 2027-01-27 23:47:00.

2027-01-24 → 2027-01-27 · Axel-exclusive $280.25

  • Southwest Airlines WN3092 / WN4807: MDW 2027-01-24 13:40:00 → JAX 2027-01-24 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2027-01-24 13:40:00 → STL 2027-01-24 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2027-01-24 18:15:00 → JAX 2027-01-24 21:15:00.
  • Southwest Airlines WN2264: JAX 2027-01-27 18:55:00 → MDW 2027-01-27 20:20:00; nonstop; 145 minutes. Local airport times.

2027-01-24 → 2027-01-28 · Axel-exclusive $190.00

  • Frontier Airlines F92144 / F91550: MDW 2027-01-24 13:11:00 → JAX 2027-01-24 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-01-24 13:11:00 → ATL 2027-01-24 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-01-24 18:09:00 → JAX 2027-01-24 19:25:00.
  • Frontier Airlines F91549 / F92291: JAX 2027-01-28 19:03:00 → MDW 2027-01-28 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-01-28 19:03:00 → ATL 2027-01-28 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-01-28 22:48:00 → MDW 2027-01-28 23:47:00.

2027-01-24 → 2027-01-28 · Axel-exclusive $294.50

  • Southwest Airlines WN3092 / WN4807: MDW 2027-01-24 13:40:00 → JAX 2027-01-24 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2027-01-24 13:40:00 → STL 2027-01-24 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2027-01-24 18:15:00 → JAX 2027-01-24 21:15:00.
  • Southwest Airlines WN2256 / WN1070: JAX 2027-01-28 08:00:00 → MDW 2027-01-28 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2027-01-28 08:00:00 → BWI 2027-01-28 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2027-01-28 11:05:00 → MDW 2027-01-28 12:15:00.

2027-01-24 → 2027-01-30 · Axel-exclusive $190.00

  • Frontier Airlines F92144 / F91550: MDW 2027-01-24 13:11:00 → JAX 2027-01-24 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-01-24 13:11:00 → ATL 2027-01-24 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-01-24 18:09:00 → JAX 2027-01-24 19:25:00.
  • Frontier Airlines F91549 / F92291: JAX 2027-01-30 19:03:00 → MDW 2027-01-30 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-01-30 19:03:00 → ATL 2027-01-30 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-01-30 22:48:00 → MDW 2027-01-30 23:47:00.

2027-01-24 → 2027-01-30 · Axel-exclusive $280.25

  • Southwest Airlines WN3092 / WN4807: MDW 2027-01-24 13:40:00 → JAX 2027-01-24 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2027-01-24 13:40:00 → STL 2027-01-24 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2027-01-24 18:15:00 → JAX 2027-01-24 21:15:00.
  • Southwest Airlines WN2264: JAX 2027-01-30 18:50:00 → MDW 2027-01-30 20:20:00; nonstop; 150 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $190.00

  • Frontier Airlines F92144 / F91550: MDW 2027-01-24 13:11:00 → JAX 2027-01-24 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-01-24 13:11:00 → ATL 2027-01-24 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-01-24 18:09:00 → JAX 2027-01-24 19:25:00.
  • Frontier Airlines F91549 / F92291: JAX 2027-01-31 19:03:00 → MDW 2027-01-31 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-01-31 19:03:00 → ATL 2027-01-31 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-01-31 22:48:00 → MDW 2027-01-31 23:47:00.

2027-01-24 → 2027-01-31 · Axel-exclusive $280.25

  • Southwest Airlines WN3092 / WN4807: MDW 2027-01-24 13:40:00 → JAX 2027-01-24 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2027-01-24 13:40:00 → STL 2027-01-24 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2027-01-24 18:15:00 → JAX 2027-01-24 21:15:00.
  • Southwest Airlines WN2264: JAX 2027-01-31 18:55:00 → MDW 2027-01-31 20:20:00; nonstop; 145 minutes. Local airport times.

2027-01-24 → 2027-02-01 · Axel-exclusive $195.00

  • Frontier Airlines F92144 / F91550: MDW 2027-01-24 13:11:00 → JAX 2027-01-24 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-01-24 13:11:00 → ATL 2027-01-24 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-01-24 18:09:00 → JAX 2027-01-24 19:25:00.
  • Frontier Airlines F91549 / F92291: JAX 2027-02-01 19:03:00 → MDW 2027-02-01 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-02-01 19:03:00 → ATL 2027-02-01 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-02-01 22:48:00 → MDW 2027-02-01 23:47:00.

2027-01-24 → 2027-02-01 · Axel-exclusive $287.25

  • Southwest Airlines WN3092 / WN4807: MDW 2027-01-24 13:40:00 → JAX 2027-01-24 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2027-01-24 13:40:00 → STL 2027-01-24 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2027-01-24 18:15:00 → JAX 2027-01-24 21:15:00.
  • Southwest Airlines WN2264: JAX 2027-02-01 18:55:00 → MDW 2027-02-01 20:20:00; nonstop; 145 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $195.00

  • Frontier Airlines F92144 / F91550: MDW 2027-01-24 13:11:00 → JAX 2027-01-24 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-01-24 13:11:00 → ATL 2027-01-24 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-01-24 18:09:00 → JAX 2027-01-24 19:25:00.
  • Frontier Airlines F91549 / F92291: JAX 2027-02-03 19:03:00 → MDW 2027-02-03 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-02-03 19:03:00 → ATL 2027-02-03 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-02-03 22:48:00 → MDW 2027-02-03 23:47:00.

2027-01-24 → 2027-02-03 · Axel-exclusive $287.25

  • Southwest Airlines WN3092 / WN4807: MDW 2027-01-24 13:40:00 → JAX 2027-01-24 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2027-01-24 13:40:00 → STL 2027-01-24 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2027-01-24 18:15:00 → JAX 2027-01-24 21:15:00.
  • Southwest Airlines WN2264: JAX 2027-02-03 18:55:00 → MDW 2027-02-03 20:20:00; nonstop; 145 minutes. Local airport times.

2027-01-24 → 2027-02-04 · Axel-exclusive $195.00

  • Frontier Airlines F92144 / F91550: MDW 2027-01-24 13:11:00 → JAX 2027-01-24 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-01-24 13:11:00 → ATL 2027-01-24 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-01-24 18:09:00 → JAX 2027-01-24 19:25:00.
  • Frontier Airlines F91549 / F92291: JAX 2027-02-04 19:03:00 → MDW 2027-02-04 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-02-04 19:03:00 → ATL 2027-02-04 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-02-04 22:48:00 → MDW 2027-02-04 23:47:00.

2027-01-24 → 2027-02-04 · Axel-exclusive $302.25

  • Southwest Airlines WN3092 / WN4807: MDW 2027-01-24 13:40:00 → JAX 2027-01-24 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2027-01-24 13:40:00 → STL 2027-01-24 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2027-01-24 18:15:00 → JAX 2027-01-24 21:15:00.
  • Southwest Airlines WN2256 / WN1070: JAX 2027-02-04 08:00:00 → MDW 2027-02-04 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2027-02-04 08:00:00 → BWI 2027-02-04 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2027-02-04 11:05:00 → MDW 2027-02-04 12:15:00.

2027-01-24 → 2027-02-05 · Axel-exclusive $195.00

  • Frontier Airlines F92144 / F91550: MDW 2027-01-24 13:11:00 → JAX 2027-01-24 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-01-24 13:11:00 → ATL 2027-01-24 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-01-24 18:09:00 → JAX 2027-01-24 19:25:00.
  • Frontier Airlines F91549 / F92291: JAX 2027-02-05 19:03:00 → MDW 2027-02-05 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-02-05 19:03:00 → ATL 2027-02-05 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-02-05 22:48:00 → MDW 2027-02-05 23:47:00.

2027-01-24 → 2027-02-05 · Axel-exclusive $287.25

  • Southwest Airlines WN3092 / WN4807: MDW 2027-01-24 13:40:00 → JAX 2027-01-24 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2027-01-24 13:40:00 → STL 2027-01-24 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2027-01-24 18:15:00 → JAX 2027-01-24 21:15:00.
  • Southwest Airlines WN2264: JAX 2027-02-05 18:50:00 → MDW 2027-02-05 20:20:00; nonstop; 150 minutes. Local airport times.

2027-01-24 → 2027-02-07 · Axel-exclusive $195.00

  • Frontier Airlines F92144 / F91550: MDW 2027-01-24 13:11:00 → JAX 2027-01-24 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-01-24 13:11:00 → ATL 2027-01-24 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-01-24 18:09:00 → JAX 2027-01-24 19:25:00.
  • Frontier Airlines F91549 / F92291: JAX 2027-02-07 19:03:00 → MDW 2027-02-07 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-02-07 19:03:00 → ATL 2027-02-07 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-02-07 22:48:00 → MDW 2027-02-07 23:47:00.

2027-01-24 → 2027-02-07 · Axel-exclusive $287.25

  • Southwest Airlines WN3092 / WN4807: MDW 2027-01-24 13:40:00 → JAX 2027-01-24 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2027-01-24 13:40:00 → STL 2027-01-24 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2027-01-24 18:15:00 → JAX 2027-01-24 21:15:00.
  • Southwest Airlines WN2264: JAX 2027-02-07 18:55:00 → MDW 2027-02-07 20:20:00; nonstop; 145 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Chicago (MDW) to Jacksonville (JAX) · Jan 24, 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: 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 Chicago to Jacksonville (JAX) 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.