Jacksonville (JAX) to Chicago (MDW) · Nov 30, 2026 · return Dec 4, 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: Jacksonville to Chicago (MDW) flight deals

2026-11-30 → 2026-12-04 · Axel-exclusive $340.75

• Southwest Airlines WN1979: JAX 2026-11-30 13:30:00 → MDW 2026-11-30 14:55:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2262: MDW 2026-12-04 08:00:00 → JAX 2026-12-04 11:25:00; nonstop; 145 minutes. Local airport times.

2026-11-30 → 2026-12-04 · Axel-exclusive $217.38

• Frontier Airlines F91549 / F92291: JAX 2026-11-30 19:03:00 → MDW 2026-11-30 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2026-11-30 19:03:00 → ATL 2026-11-30 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2026-11-30 22:48:00 → MDW 2026-11-30 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2026-12-04 13:11:00 → JAX 2026-12-04 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2026-12-04 13:11:00 → ATL 2026-12-04 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2026-12-04 18:09:00 → JAX 2026-12-04 19:25:00.

2026-11-30 → 2026-12-04 · Axel-exclusive $387.75

• Delta Air Lines DL2627 / DL1076: JAX 2026-11-30 18:59:00 → MDW 2026-11-30 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
  • DL2627: JAX 2026-11-30 18:59:00 → ATL 2026-11-30 20:19:00; layover at ATL: 61 minutes.
  • DL1076: ATL 2026-11-30 21:20:00 → MDW 2026-11-30 22:17:00.
• Delta Air Lines DL2417 / DL2265: MDW 2026-12-04 13:02:00 → JAX 2026-12-04 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
  • DL2417: MDW 2026-12-04 13:02:00 → ATL 2026-12-04 16:01:00; layover at ATL: 212 minutes.
  • DL2265: ATL 2026-12-04 19:33:00 → JAX 2026-12-04 20:43:00.

2026-11-30 → 2026-12-04 · Axel-exclusive $340.75

• Southwest Airlines WN2264: JAX 2026-11-30 18:55:00 → MDW 2026-11-30 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2262: MDW 2026-12-04 08:00:00 → JAX 2026-12-04 11:25:00; nonstop; 145 minutes. Local airport times.

2026-11-30 → 2026-12-04 · Axel-exclusive $330.63

• Southwest Airlines WN2256 / WN1070: JAX 2026-11-30 08:00:00 → MDW 2026-11-30 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2026-11-30 08:00:00 → BWI 2026-11-30 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2026-11-30 11:05:00 → MDW 2026-11-30 12:15:00.
• Southwest Airlines WN2262: MDW 2026-12-04 08:00:00 → JAX 2026-12-04 11:25:00; nonstop; 145 minutes. Local airport times.

2026-11-30 → 2026-12-04 · Axel-exclusive $330.63

• Southwest Airlines WN2253 / WN2062: JAX 2026-11-30 11:20:00 → MDW 2026-11-30 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
  • WN2253: JAX 2026-11-30 11:20:00 → BNA 2026-11-30 12:05:00; layover at BNA: 160 minutes.
  • WN2062: BNA 2026-11-30 14:45:00 → MDW 2026-11-30 16:15:00.
• Southwest Airlines WN2262: MDW 2026-12-04 08:00:00 → JAX 2026-12-04 11:25:00; nonstop; 145 minutes. Local airport times.

2026-11-30 → 2026-12-04 · Axel-exclusive $333.25

• Southwest Airlines WN2264: JAX 2026-11-30 18:50:00 → MDW 2026-11-30 20:20:00; nonstop; 150 minutes. Local airport times.
• Southwest Airlines WN2897 / WN1516: MDW 2026-12-04 17:25:00 → JAX 2026-12-04 23:45:00; 1 stop(s) via BNA; 320 minutes. Local airport times.
  • WN2897: MDW 2026-12-04 17:25:00 → BNA 2026-12-04 18:50:00; layover at BNA: 140 minutes.
  • WN1516: BNA 2026-12-04 21:10:00 → JAX 2026-12-04 23:45:00.

2026-11-30 → 2026-12-04 · Axel-exclusive $387.75

• Delta Air Lines DL2333 / DL4677: JAX 2026-11-30 12:00:00 → MDW 2026-11-30 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
  • DL2333: JAX 2026-11-30 12:00:00 → DTW 2026-11-30 14:20:00; layover at DTW: 200 minutes.
  • DL4677: DTW 2026-11-30 17:40:00 → MDW 2026-11-30 18:01:00.
• Delta Air Lines DL2417 / DL2265: MDW 2026-12-04 13:02:00 → JAX 2026-12-04 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
  • DL2417: MDW 2026-12-04 13:02:00 → ATL 2026-12-04 16:01:00; layover at ATL: 212 minutes.
  • DL2265: ATL 2026-12-04 19:33:00 → JAX 2026-12-04 20:43:00.

Explore this route

• All dates for this route
• Nov 29, 2026 · Return options
• Dec 1, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Jacksonville (JAX) to Chicago (MDW) · Nov 30, 2026 · return Dec 4, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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