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Chicago → Jacksonville

Dec 3, 2026 · return Dec 7, 2026

MDW → JAX1 adulteconomyRound trip

8 flight options · 3 airlines

Nonstop flights

Thu, Dec 3 – Mon, Dec 7

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

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Mon, Dec 7

Southwest Airlines
7:00 pmMDW
2h 15m
Nonstop
10:15 pmJAX
Southwest Airlines
6:55 pmJAX
2h 25m
Nonstop
8:20 pmMDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Thu, Dec 3 – Mon, Dec 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

Thu, Dec 3 – Mon, Dec 7

Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX
Delta Air Lines
6:59 pmJAX
4h 18m
ATL · 1h 1m
10:17 pmMDW

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Mon, Dec 7

Southwest Airlines
5:25 pmMDW
5h 20m
BNA · 2h 20m
11:45 pmJAX
Southwest Airlines
6:55 pmJAX
2h 25m
Nonstop
8:20 pmMDW

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Mon, Dec 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

Thu, Dec 3 – Mon, Dec 7

Southwest Airlines
2:30 pmMDW
5h 5m
BWI · 1h 5m
8:35 pmJAX
Southwest Airlines
6:55 pmJAX
2h 25m
Nonstop
8:20 pmMDW

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Mon, Dec 7

Delta Air Lines
9:30 amMDW
7h 8m
DTW · 3h 30m
5:38 pmJAX
Delta Air Lines
6:59 pmJAX
4h 18m
ATL · 1h 1m
10:17 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ JAX

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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More dates

All dates for this routeNov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-03 → 2026-12-07Southwest AirlinesWN2041 / WN2264$280.002026-10-29T01:29:09Z
2026-12-03 → 2026-12-07Frontier AirlinesF92144 + F91550 / F91549 + F92291$200.002026-10-29T01:29:09Z
2026-12-03 → 2026-12-07Delta Air LinesDL2417 + DL2265 / DL2627 + DL1076$350.002026-10-29T01:29:09Z
2026-12-03 → 2026-12-07Southwest AirlinesWN2946 / WN2264$280.002026-10-29T01:29:09Z
2026-12-03 → 2026-12-07Southwest AirlinesWN2897 + WN1516 / WN2264$295.002026-10-29T01:29:09Z
2026-12-03 → 2026-12-07Southwest AirlinesWN3092 + WN4807 / WN2264$295.002026-10-29T01:29:09Z
2026-12-03 → 2026-12-07Southwest AirlinesWN14 + WN1041 / WN2264$295.002026-10-29T01:29:09Z
2026-12-03 → 2026-12-07Delta Air LinesDL4711 + DL2994 / DL2627 + DL1076$350.002026-10-29T01:29:09Z

2026-12-03 → 2026-12-07 · $280.00

  • Southwest Airlines WN2041: MDW 2026-12-03 12:50:00 → JAX 2026-12-03 16:05:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN2264: JAX 2026-12-07 18:55:00 → MDW 2026-12-07 20:20:00; nonstop; 145 minutes. Local airport times.

2026-12-03 → 2026-12-07 · $200.00

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

2026-12-03 → 2026-12-07 · $350.00

  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-03 13:02:00 → JAX 2026-12-03 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-03 13:02:00 → ATL 2026-12-03 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-03 19:33:00 → JAX 2026-12-03 20:43:00.
  • Delta Air Lines DL2627 / DL1076: JAX 2026-12-07 18:59:00 → MDW 2026-12-07 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2026-12-07 18:59:00 → ATL 2026-12-07 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2026-12-07 21:20:00 → MDW 2026-12-07 22:17:00.

2026-12-03 → 2026-12-07 · $280.00

  • Southwest Airlines WN2946: MDW 2026-12-03 19:00:00 → JAX 2026-12-03 22:15:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN2264: JAX 2026-12-07 18:55:00 → MDW 2026-12-07 20:20:00; nonstop; 145 minutes. Local airport times.

2026-12-03 → 2026-12-07 · $295.00

  • Southwest Airlines WN2897 / WN1516: MDW 2026-12-03 17:25:00 → JAX 2026-12-03 23:45:00; 1 stop(s) via BNA; 320 minutes. Local airport times.
    • WN2897: MDW 2026-12-03 17:25:00 → BNA 2026-12-03 18:50:00; layover at BNA: 140 minutes.
    • WN1516: BNA 2026-12-03 21:10:00 → JAX 2026-12-03 23:45:00.
  • Southwest Airlines WN2264: JAX 2026-12-07 18:55:00 → MDW 2026-12-07 20:20:00; nonstop; 145 minutes. Local airport times.

2026-12-03 → 2026-12-07 · $295.00

  • Southwest Airlines WN3092 / WN4807: MDW 2026-12-03 13:40:00 → JAX 2026-12-03 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
    • WN3092: MDW 2026-12-03 13:40:00 → STL 2026-12-03 14:55:00; layover at STL: 200 minutes.
    • WN4807: STL 2026-12-03 18:15:00 → JAX 2026-12-03 21:15:00.
  • Southwest Airlines WN2264: JAX 2026-12-07 18:55:00 → MDW 2026-12-07 20:20:00; nonstop; 145 minutes. Local airport times.

2026-12-03 → 2026-12-07 · $295.00

  • Southwest Airlines WN14 / WN1041: MDW 2026-12-03 14:30:00 → JAX 2026-12-03 20:35:00; 1 stop(s) via BWI; 305 minutes. Local airport times.
    • WN14: MDW 2026-12-03 14:30:00 → BWI 2026-12-03 17:15:00; layover at BWI: 65 minutes.
    • WN1041: BWI 2026-12-03 18:20:00 → JAX 2026-12-03 20:35:00.
  • Southwest Airlines WN2264: JAX 2026-12-07 18:55:00 → MDW 2026-12-07 20:20:00; nonstop; 145 minutes. Local airport times.

2026-12-03 → 2026-12-07 · $350.00

  • Delta Air Lines DL4711 / DL2994: MDW 2026-12-03 09:30:00 → JAX 2026-12-03 17:38:00; 1 stop(s) via DTW; 428 minutes. Local airport times.
    • DL4711: MDW 2026-12-03 09:30:00 → DTW 2026-12-03 11:45:00; layover at DTW: 210 minutes.
    • DL2994: DTW 2026-12-03 15:15:00 → JAX 2026-12-03 17:38:00.
  • Delta Air Lines DL2627 / DL1076: JAX 2026-12-07 18:59:00 → MDW 2026-12-07 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2026-12-07 18:59:00 → ATL 2026-12-07 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2026-12-07 21:20:00 → MDW 2026-12-07 22:17:00.

More dates for this route