Jacksonville (JAX) to Chicago (MDW) · Dec 28, 2026 · return Jan 11, 2027

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

2026-12-28 → 2027-01-11 · Axel-exclusive $333.50

• Southwest Airlines WN2264: JAX 2026-12-28 18:55:00 → MDW 2026-12-28 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2946: MDW 2027-01-11 19:00:00 → JAX 2027-01-11 22:15:00; nonstop; 135 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $212.76

• Frontier Airlines F91549 / F92291: JAX 2026-12-28 19:03:00 → MDW 2026-12-28 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2026-12-28 19:03:00 → ATL 2026-12-28 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2026-12-28 22:48:00 → MDW 2026-12-28 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-01-11 13:11:00 → JAX 2027-01-11 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-01-11 13:11:00 → ATL 2027-01-11 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-01-11 18:09:00 → JAX 2027-01-11 19:25:00.

2026-12-28 → 2027-01-11 · Axel-exclusive $379.50

• Delta Air Lines DL2333 / DL4677: JAX 2026-12-28 12:00:00 → MDW 2026-12-28 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
  • DL2333: JAX 2026-12-28 12:00:00 → DTW 2026-12-28 14:20:00; layover at DTW: 200 minutes.
  • DL4677: DTW 2026-12-28 17:40:00 → MDW 2026-12-28 18:01:00.
• Delta Air Lines DL2417 / DL2265: MDW 2027-01-11 13:02:00 → JAX 2027-01-11 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
  • DL2417: MDW 2027-01-11 13:02:00 → ATL 2027-01-11 16:01:00; layover at ATL: 212 minutes.
  • DL2265: ATL 2027-01-11 19:33:00 → JAX 2027-01-11 20:43:00.

2026-12-28 → 2027-01-11 · Axel-exclusive $333.50

• Southwest Airlines WN1979: JAX 2026-12-28 13:30:00 → MDW 2026-12-28 14:55:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2946: MDW 2027-01-11 19:00:00 → JAX 2027-01-11 22:15:00; nonstop; 135 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $323.38

• Southwest Airlines WN2265 / WN287: JAX 2026-12-28 06:00:00 → MDW 2026-12-28 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
  • WN2265: JAX 2026-12-28 06:00:00 → STL 2026-12-28 07:20:00; layover at STL: 215 minutes.
  • WN287: STL 2026-12-28 10:55:00 → MDW 2026-12-28 12:05:00.
• Southwest Airlines WN2946: MDW 2027-01-11 19:00:00 → JAX 2027-01-11 22:15:00; nonstop; 135 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $323.38

• Southwest Airlines WN2256 / WN1070: JAX 2026-12-28 08:00:00 → MDW 2026-12-28 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2026-12-28 08:00:00 → BWI 2026-12-28 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2026-12-28 11:05:00 → MDW 2026-12-28 12:15:00.
• Southwest Airlines WN2946: MDW 2027-01-11 19:00:00 → JAX 2027-01-11 22:15:00; nonstop; 135 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $323.38

• Southwest Airlines WN2253 / WN2062: JAX 2026-12-28 11:20:00 → MDW 2026-12-28 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
  • WN2253: JAX 2026-12-28 11:20:00 → BNA 2026-12-28 12:05:00; layover at BNA: 160 minutes.
  • WN2062: BNA 2026-12-28 14:45:00 → MDW 2026-12-28 16:15:00.
• Southwest Airlines WN2946: MDW 2027-01-11 19:00:00 → JAX 2027-01-11 22:15:00; nonstop; 135 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $379.50

• Delta Air Lines DL2627 / DL1076: JAX 2026-12-28 18:59:00 → MDW 2026-12-28 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
  • DL2627: JAX 2026-12-28 18:59:00 → ATL 2026-12-28 20:19:00; layover at ATL: 61 minutes.
  • DL1076: ATL 2026-12-28 21:20:00 → MDW 2026-12-28 22:17:00.
• Delta Air Lines DL2417 / DL2265: MDW 2027-01-11 13:02:00 → JAX 2027-01-11 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
  • DL2417: MDW 2027-01-11 13:02:00 → ATL 2027-01-11 16:01:00; layover at ATL: 212 minutes.
  • DL2265: ATL 2027-01-11 19:33:00 → JAX 2027-01-11 20:43:00.

Explore this route

• All dates for this route
• Dec 27, 2026 · Return options
• Dec 29, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Jacksonville (JAX) to Chicago (MDW) · Dec 28, 2026 · return Jan 11, 2027: 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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