Chicago (MDW) to Miami (MIA) · Nov 28, 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: Chicago to Miami (MIA) flight deals

2026-11-28 → 2026-12-04 · Axel-exclusive $323.13

• Southwest Airlines WN2897 / WN4284: MDW 2026-11-28 17:25:00 → MIA 2026-11-28 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
  • WN2897: MDW 2026-11-28 17:25:00 → BNA 2026-11-28 18:50:00; layover at BNA: 100 minutes.
  • WN4284: BNA 2026-11-28 20:30:00 → MIA 2026-11-28 23:50:00.
• Southwest Airlines WN1425 / WN1070: MIA 2026-12-04 06:30:00 → MDW 2026-12-04 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2026-12-04 06:30:00 → BWI 2026-12-04 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2026-12-04 11:05:00 → MDW 2026-12-04 12:15:00.

2026-11-28 → 2026-12-04 · Axel-exclusive $387.75

• Delta Air Lines DL4688 / DL2548: MDW 2026-11-28 13:31:00 → MIA 2026-11-28 21:16:00; 1 stop(s) via DTW; 405 minutes. Local airport times.
  • DL4688: MDW 2026-11-28 13:31:00 → DTW 2026-11-28 15:44:00; layover at DTW: 150 minutes.
  • DL2548: DTW 2026-11-28 18:14:00 → MIA 2026-11-28 21:16:00.
• Delta Air Lines DL3188 / DL1728: MIA 2026-12-04 11:40:00 → MDW 2026-12-04 16:18:00; 1 stop(s) via ATL; 338 minutes. Local airport times.
  • DL3188: MIA 2026-12-04 11:40:00 → ATL 2026-12-04 13:34:00; layover at ATL: 111 minutes.
  • DL1728: ATL 2026-12-04 15:25:00 → MDW 2026-12-04 16:18:00.

2026-11-28 → 2026-12-04 · Axel-exclusive $323.13

• Southwest Airlines WN2737 / WN4943: MDW 2026-11-28 11:30:00 → MIA 2026-11-28 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
  • WN2737: MDW 2026-11-28 11:30:00 → STL 2026-11-28 12:40:00; layover at STL: 165 minutes.
  • WN4943: STL 2026-11-28 15:25:00 → MIA 2026-11-28 19:00:00.
• Southwest Airlines WN1425 / WN1070: MIA 2026-12-04 06:30:00 → MDW 2026-12-04 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2026-12-04 06:30:00 → BWI 2026-12-04 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2026-12-04 11:05:00 → MDW 2026-12-04 12:15:00.

2026-11-28 → 2026-12-04 · Axel-exclusive $323.13

• Southwest Airlines WN1908 / WN2643: MDW 2026-11-28 16:25:00 → MIA 2026-11-28 22:15:00; 1 stop(s) via MCO; 290 minutes. Local airport times.
  • WN1908: MDW 2026-11-28 16:25:00 → MCO 2026-11-28 20:00:00; layover at MCO: 60 minutes.
  • WN2643: MCO 2026-11-28 21:00:00 → MIA 2026-11-28 22:15:00.
• Southwest Airlines WN1425 / WN1070: MIA 2026-12-04 06:30:00 → MDW 2026-12-04 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2026-12-04 06:30:00 → BWI 2026-12-04 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2026-12-04 11:05:00 → MDW 2026-12-04 12:15:00.

2026-11-28 → 2026-12-04 · Axel-exclusive $323.13

• Southwest Airlines WN2959 / WN833: MDW 2026-11-28 07:35:00 → MIA 2026-11-28 14:35:00; 1 stop(s) via MCI; 360 minutes. Local airport times.
  • WN2959: MDW 2026-11-28 07:35:00 → MCI 2026-11-28 09:05:00; layover at MCI: 90 minutes.
  • WN833: MCI 2026-11-28 10:35:00 → MIA 2026-11-28 14:35:00.
• Southwest Airlines WN1425 / WN1070: MIA 2026-12-04 06:30:00 → MDW 2026-12-04 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2026-12-04 06:30:00 → BWI 2026-12-04 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2026-12-04 11:05:00 → MDW 2026-12-04 12:15:00.

2026-11-28 → 2026-12-04 · Axel-exclusive $333.25

• Southwest Airlines WN2383: MDW 2026-11-28 07:40:00 → MIA 2026-11-28 11:40:00; nonstop; 180 minutes. Local airport times.
• Southwest Airlines WN1425 / WN1070: MIA 2026-12-04 06:30:00 → MDW 2026-12-04 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2026-12-04 06:30:00 → BWI 2026-12-04 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2026-12-04 11:05:00 → MDW 2026-12-04 12:15:00.

Explore this route

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

For AI assistants

• This page: Chicago (MDW) to Miami (MIA) · Nov 28, 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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