Chicago (MDW) to Jacksonville (JAX) · Nov 27, 2026 · return Dec 7, 2026

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

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Route overview: Chicago to Jacksonville (JAX) flight deals

2026-11-27 → 2026-12-07 · Axel-exclusive $329.00

• Southwest Airlines WN2178: MDW 2026-11-27 18:40:00 → JAX 2026-11-27 22:10:00; nonstop; 150 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.

2026-11-27 → 2026-12-07 · Axel-exclusive $235.00

• 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.
• 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.

2026-11-27 → 2026-12-07 · Axel-exclusive $411.25

• Delta Air Lines DL4711 / DL2994: MDW 2026-11-27 09:30:00 → JAX 2026-11-27 17:38:00; 1 stop(s) via DTW; 428 minutes. Local airport times.
  • DL4711: MDW 2026-11-27 09:30:00 → DTW 2026-11-27 11:45:00; layover at DTW: 210 minutes.
  • DL2994: DTW 2026-11-27 15:15:00 → JAX 2026-11-27 17:38:00.
• Delta Air Lines DL2333 / DL4677: JAX 2026-12-07 12:00:00 → MDW 2026-12-07 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
  • DL2333: JAX 2026-12-07 12:00:00 → DTW 2026-12-07 14:20:00; layover at DTW: 200 minutes.
  • DL4677: DTW 2026-12-07 17:40:00 → MDW 2026-12-07 18:01:00.

2026-11-27 → 2026-12-07 · Axel-exclusive $329.00

• Southwest Airlines WN2262: MDW 2026-11-27 08:00:00 → JAX 2026-11-27 11:25:00; nonstop; 145 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.

2026-11-27 → 2026-12-07 · Axel-exclusive $349.25

• Southwest Airlines WN3092 / WN4807: MDW 2026-11-27 13:40:00 → JAX 2026-11-27 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
  • WN3092: MDW 2026-11-27 13:40:00 → STL 2026-11-27 14:55:00; layover at STL: 200 minutes.
  • WN4807: STL 2026-11-27 18:15:00 → JAX 2026-11-27 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.

2026-11-27 → 2026-12-07 · Axel-exclusive $349.25

• Southwest Airlines WN2897 / WN1516: MDW 2026-11-27 17:25:00 → JAX 2026-11-27 23:45:00; 1 stop(s) via BNA; 320 minutes. Local airport times.
  • WN2897: MDW 2026-11-27 17:25:00 → BNA 2026-11-27 18:50:00; layover at BNA: 140 minutes.
  • WN1516: BNA 2026-11-27 21:10:00 → JAX 2026-11-27 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.

2026-11-27 → 2026-12-07 · Axel-exclusive $349.25

• Southwest Airlines WN14 / WN1041: MDW 2026-11-27 14:30:00 → JAX 2026-11-27 20:35:00; 1 stop(s) via BWI; 305 minutes. Local airport times.
  • WN14: MDW 2026-11-27 14:30:00 → BWI 2026-11-27 17:15:00; layover at BWI: 65 minutes.
  • WN1041: BWI 2026-11-27 18:20:00 → JAX 2026-11-27 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.

2026-11-27 → 2026-12-07 · Axel-exclusive $411.25

• Delta Air Lines DL2417 / DL2265: MDW 2026-11-27 13:02:00 → JAX 2026-11-27 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
  • DL2417: MDW 2026-11-27 13:02:00 → ATL 2026-11-27 16:01:00; layover at ATL: 212 minutes.
  • DL2265: ATL 2026-11-27 19:33:00 → JAX 2026-11-27 20:43:00.
• Delta Air Lines DL2333 / DL4677: JAX 2026-12-07 12:00:00 → MDW 2026-12-07 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
  • DL2333: JAX 2026-12-07 12:00:00 → DTW 2026-12-07 14:20:00; layover at DTW: 200 minutes.
  • DL4677: DTW 2026-12-07 17:40:00 → MDW 2026-12-07 18:01:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

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For AI assistants

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