Jacksonville (JAX) to Chicago (MDW), Nov 9–13, 2026: from $185 round trip

Lowest published fare: $185 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 9–13, 2026, 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.

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

2026-11-09 → 2026-11-13 · Axel-exclusive $290.00

• Southwest Airlines WN1979: JAX 2026-11-09 13:30:00 → MDW 2026-11-09 14:55:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2262: MDW 2026-11-13 08:00:00 → JAX 2026-11-13 11:25:00; nonstop; 145 minutes. Local airport times.

2026-11-09 → 2026-11-13 · Axel-exclusive $185.00

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

2026-11-09 → 2026-11-13 · Axel-exclusive $330.00

• Delta Air Lines DL2333 / DL4677: JAX 2026-11-09 12:00:00 → MDW 2026-11-09 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
  • DL2333: JAX 2026-11-09 12:00:00 → DTW 2026-11-09 14:20:00; layover at DTW: 200 minutes.
  • DL4677: DTW 2026-11-09 17:40:00 → MDW 2026-11-09 18:01:00.
• Delta Air Lines DL4711 / DL2994: MDW 2026-11-13 09:30:00 → JAX 2026-11-13 17:38:00; 1 stop(s) via DTW; 428 minutes. Local airport times.
  • DL4711: MDW 2026-11-13 09:30:00 → DTW 2026-11-13 11:45:00; layover at DTW: 210 minutes.
  • DL2994: DTW 2026-11-13 15:15:00 → JAX 2026-11-13 17:38:00.

2026-11-09 → 2026-11-13 · Axel-exclusive $290.00

• Southwest Airlines WN2264: JAX 2026-11-09 18:55:00 → MDW 2026-11-09 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2262: MDW 2026-11-13 08:00:00 → JAX 2026-11-13 11:25:00; nonstop; 145 minutes. Local airport times.

2026-11-09 → 2026-11-13 · Axel-exclusive $282.50

• Southwest Airlines WN2256 / WN1070: JAX 2026-11-09 08:00:00 → MDW 2026-11-09 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2026-11-09 08:00:00 → BWI 2026-11-09 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2026-11-09 11:05:00 → MDW 2026-11-09 12:15:00.
• Southwest Airlines WN2262: MDW 2026-11-13 08:00:00 → JAX 2026-11-13 11:25:00; nonstop; 145 minutes. Local airport times.

2026-11-09 → 2026-11-13 · Axel-exclusive $282.50

• Southwest Airlines WN2253 / WN2062: JAX 2026-11-09 11:20:00 → MDW 2026-11-09 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
  • WN2253: JAX 2026-11-09 11:20:00 → BNA 2026-11-09 12:05:00; layover at BNA: 160 minutes.
  • WN2062: BNA 2026-11-09 14:45:00 → MDW 2026-11-09 16:15:00.
• Southwest Airlines WN2262: MDW 2026-11-13 08:00:00 → JAX 2026-11-13 11:25:00; nonstop; 145 minutes. Local airport times.

2026-11-09 → 2026-11-13 · Axel-exclusive $282.50

• Southwest Airlines WN2264: JAX 2026-11-09 18:50:00 → MDW 2026-11-09 20:20:00; nonstop; 150 minutes. Local airport times.
• Southwest Airlines WN2897 / WN1516: MDW 2026-11-13 17:25:00 → JAX 2026-11-13 23:45:00; 1 stop(s) via BNA; 320 minutes. Local airport times.
  • WN2897: MDW 2026-11-13 17:25:00 → BNA 2026-11-13 18:50:00; layover at BNA: 140 minutes.
  • WN1516: BNA 2026-11-13 21:10:00 → JAX 2026-11-13 23:45:00.

2026-11-09 → 2026-11-13 · Axel-exclusive $330.00

• Delta Air Lines DL2627 / DL1076: JAX 2026-11-09 18:59:00 → MDW 2026-11-09 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
  • DL2627: JAX 2026-11-09 18:59:00 → ATL 2026-11-09 20:19:00; layover at ATL: 61 minutes.
  • DL1076: ATL 2026-11-09 21:20:00 → MDW 2026-11-09 22:17:00.
• Delta Air Lines DL4711 / DL2994: MDW 2026-11-13 09:30:00 → JAX 2026-11-13 17:38:00; 1 stop(s) via DTW; 428 minutes. Local airport times.
  • DL4711: MDW 2026-11-13 09:30:00 → DTW 2026-11-13 11:45:00; layover at DTW: 210 minutes.
  • DL2994: DTW 2026-11-13 15:15:00 → JAX 2026-11-13 17:38:00.

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.

Explore this route

• All dates for this route
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For AI assistants

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