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Chicago → Jacksonville

Dec 21, 2026 · one way

MDW → JAX1 adulteconomyOne way

8 flight options · 3 airlines

Nonstop flights

Mon, Dec 21 · One way

Southwest Airlines
7:00 pmMDW
2h 15m
Nonstop
10:15 pmJAX

One-way total · 1 adult · Taxes included

Mon, Dec 21 · One way

Southwest Airlines
12:50 pmMDW
2h 15m
Nonstop
4:05 pmJAX

One-way total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 · One way

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

One-way total · 1 adult · Taxes included

Mon, Dec 21 · One way

Delta Air Lines
9:30 amMDW
7h 8m
DTW · 3h 30m
5:38 pmJAX

One-way total · 1 adult · Taxes included

Mon, Dec 21 · One way

Southwest Airlines
2:30 pmMDW
5h 5m
BWI · 1h 5m
8:35 pmJAX

One-way total · 1 adult · Taxes included

Mon, Dec 21 · One way

Southwest Airlines
5:25 pmMDW
5h 20m
BNA · 2h 20m
11:45 pmJAX

One-way total · 1 adult · Taxes included

Mon, Dec 21 · One way

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

One-way total · 1 adult · Taxes included

Mon, Dec 21 · One way

Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

One-way 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)
2026-12-21 · one waySouthwest AirlinesWN2946$203.002026-10-29T01:29:09Z
2026-12-21 · one wayFrontier AirlinesF92144 + F91550$147.002026-10-29T01:29:09Z
2026-12-21 · one wayDelta Air LinesDL4711 + DL2994$259.002026-10-29T01:29:09Z
2026-12-21 · one waySouthwest AirlinesWN2041$203.002026-10-29T01:29:09Z
2026-12-21 · one waySouthwest AirlinesWN14 + WN1041$224.002026-10-29T01:29:09Z
2026-12-21 · one waySouthwest AirlinesWN2897 + WN1516$224.002026-10-29T01:29:09Z
2026-12-21 · one waySouthwest AirlinesWN3092 + WN4807$224.002026-10-29T01:29:09Z
2026-12-21 · one wayDelta Air LinesDL2417 + DL2265$259.002026-10-29T01:29:09Z

2026-12-21 · one way · $203.00

  • Southwest Airlines WN2946: MDW 2026-12-21 19:00:00 → JAX 2026-12-21 22:15:00; nonstop; 135 minutes. Local airport times.

2026-12-21 · one way · $147.00

  • Frontier Airlines F92144 / F91550: MDW 2026-12-21 13:11:00 → JAX 2026-12-21 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-21 13:11:00 → ATL 2026-12-21 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-21 18:09:00 → JAX 2026-12-21 19:25:00.

2026-12-21 · one way · $259.00

  • Delta Air Lines DL4711 / DL2994: MDW 2026-12-21 09:30:00 → JAX 2026-12-21 17:38:00; 1 stop(s) via DTW; 428 minutes. Local airport times.
    • DL4711: MDW 2026-12-21 09:30:00 → DTW 2026-12-21 11:45:00; layover at DTW: 210 minutes.
    • DL2994: DTW 2026-12-21 15:15:00 → JAX 2026-12-21 17:38:00.

2026-12-21 · one way · $203.00

  • Southwest Airlines WN2041: MDW 2026-12-21 12:50:00 → JAX 2026-12-21 16:05:00; nonstop; 135 minutes. Local airport times.

2026-12-21 · one way · $224.00

  • Southwest Airlines WN14 / WN1041: MDW 2026-12-21 14:30:00 → JAX 2026-12-21 20:35:00; 1 stop(s) via BWI; 305 minutes. Local airport times.
    • WN14: MDW 2026-12-21 14:30:00 → BWI 2026-12-21 17:15:00; layover at BWI: 65 minutes.
    • WN1041: BWI 2026-12-21 18:20:00 → JAX 2026-12-21 20:35:00.

2026-12-21 · one way · $224.00

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

2026-12-21 · one way · $224.00

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

2026-12-21 · one way · $259.00

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

More dates for this route