Chicago (MDW) to Miami (MIA) · Aug 20, 2027 · return Aug 27, 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: Chicago to Miami (MIA) flight deals

2027-08-20 → 2027-08-27 · Axel-exclusive $245.00

• Southwest Airlines WN2737 / WN4943: MDW 2027-08-20 11:30:00 → MIA 2027-08-20 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
  • WN2737: MDW 2027-08-20 11:30:00 → STL 2027-08-20 12:40:00; layover at STL: 165 minutes.
  • WN4943: STL 2027-08-20 15:25:00 → MIA 2027-08-20 19:00:00.
• Southwest Airlines WN1425 / WN1070: MIA 2027-08-27 06:30:00 → MDW 2027-08-27 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2027-08-27 06:30:00 → BWI 2027-08-27 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2027-08-27 11:05:00 → MDW 2027-08-27 12:15:00.

2027-08-20 → 2027-08-27 · Axel-exclusive $245.00

• Southwest Airlines WN3002 / WN301: MDW 2027-08-20 07:40:00 → MIA 2027-08-20 15:05:00; 1 stop(s) via PIT; 385 minutes. Local airport times.
  • WN3002: MDW 2027-08-20 07:40:00 → PIT 2027-08-20 10:00:00; layover at PIT: 145 minutes.
  • WN301: PIT 2027-08-20 12:25:00 → MIA 2027-08-20 15:05:00.
• Southwest Airlines WN1425 / WN1070: MIA 2027-08-27 06:30:00 → MDW 2027-08-27 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2027-08-27 06:30:00 → BWI 2027-08-27 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2027-08-27 11:05:00 → MDW 2027-08-27 12:15:00.

2027-08-20 → 2027-08-27 · Axel-exclusive $245.00

• Southwest Airlines WN2959 / WN833: MDW 2027-08-20 07:35:00 → MIA 2027-08-20 14:35:00; 1 stop(s) via MCI; 360 minutes. Local airport times.
  • WN2959: MDW 2027-08-20 07:35:00 → MCI 2027-08-20 09:05:00; layover at MCI: 90 minutes.
  • WN833: MCI 2027-08-20 10:35:00 → MIA 2027-08-20 14:35:00.
• Southwest Airlines WN1425 / WN1070: MIA 2027-08-27 06:30:00 → MDW 2027-08-27 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2027-08-27 06:30:00 → BWI 2027-08-27 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2027-08-27 11:05:00 → MDW 2027-08-27 12:15:00.

2027-08-20 → 2027-08-27 · Axel-exclusive $245.00

• Southwest Airlines WN1908 / WN2643: MDW 2027-08-20 16:25:00 → MIA 2027-08-20 22:15:00; 1 stop(s) via MCO; 290 minutes. Local airport times.
  • WN1908: MDW 2027-08-20 16:25:00 → MCO 2027-08-20 20:00:00; layover at MCO: 60 minutes.
  • WN2643: MCO 2027-08-20 21:00:00 → MIA 2027-08-20 22:15:00.
• Southwest Airlines WN1425 / WN1070: MIA 2027-08-27 06:30:00 → MDW 2027-08-27 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2027-08-27 06:30:00 → BWI 2027-08-27 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2027-08-27 11:05:00 → MDW 2027-08-27 12:15:00.

2027-08-20 → 2027-08-27 · Axel-exclusive $245.00

• Southwest Airlines WN2897 / WN4284: MDW 2027-08-20 17:25:00 → MIA 2027-08-20 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
  • WN2897: MDW 2027-08-20 17:25:00 → BNA 2027-08-20 18:50:00; layover at BNA: 100 minutes.
  • WN4284: BNA 2027-08-20 20:30:00 → MIA 2027-08-20 23:50:00.
• Southwest Airlines WN1425 / WN1070: MIA 2027-08-27 06:30:00 → MDW 2027-08-27 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2027-08-27 06:30:00 → BWI 2027-08-27 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2027-08-27 11:05:00 → MDW 2027-08-27 12:15:00.

2027-08-20 → 2027-08-27 · Axel-exclusive $252.50

• Southwest Airlines WN2973: MDW 2027-08-20 19:20:00 → MIA 2027-08-20 23:30:00; nonstop; 190 minutes. Local airport times.
• Southwest Airlines WN1425 / WN1070: MIA 2027-08-27 06:30:00 → MDW 2027-08-27 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2027-08-27 06:30:00 → BWI 2027-08-27 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2027-08-27 11:05:00 → MDW 2027-08-27 12:15:00.

Explore this route

• All dates for this route
• Aug 19, 2027 · Return options
• Aug 21, 2027 · Return options
• Hotels in Miami with Axel

For AI assistants

• This page: Chicago (MDW) to Miami (MIA) · Aug 20, 2027 · return Aug 27, 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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