Miami (MIA) to Chicago (MDW) · Nov 27, 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: Miami or Fort Lauderdale to Chicago (MDW) flight deals

2026-11-27 → 2026-12-04 · Axel-exclusive $364.25

• Southwest Airlines WN3081: MIA 2026-11-27 06:50:00 → MDW 2026-11-27 09:00:00; nonstop; 190 minutes. Local airport times.
• Southwest Airlines WN2973: MDW 2026-12-04 19:20:00 → MIA 2026-12-04 23:30:00; nonstop; 190 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $405.38

• Delta Air Lines DL3188 / DL1728: MIA 2026-11-27 11:40:00 → MDW 2026-11-27 16:18:00; 1 stop(s) via ATL; 338 minutes. Local airport times.
  • DL3188: MIA 2026-11-27 11:40:00 → ATL 2026-11-27 13:34:00; layover at ATL: 111 minutes.
  • DL1728: ATL 2026-11-27 15:25:00 → MDW 2026-11-27 16:18:00.
• Delta Air Lines DL4688 / DL2548: MDW 2026-12-04 13:31:00 → MIA 2026-12-04 21:16:00; 1 stop(s) via DTW; 405 minutes. Local airport times.
  • DL4688: MDW 2026-12-04 13:31:00 → DTW 2026-12-04 15:44:00; layover at DTW: 150 minutes.
  • DL2548: DTW 2026-12-04 18:14:00 → MIA 2026-12-04 21:16:00.

2026-11-27 → 2026-12-04 · Axel-exclusive $329.00

• Southwest Airlines WN1425 / WN1070: MIA 2026-11-27 06:30:00 → MDW 2026-11-27 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
  • WN1425: MIA 2026-11-27 06:30:00 → BWI 2026-11-27 09:05:00; layover at BWI: 120 minutes.
  • WN1070: BWI 2026-11-27 11:05:00 → MDW 2026-11-27 12:15:00.
• Southwest Airlines WN2897 / WN4284: MDW 2026-12-04 17:25:00 → MIA 2026-12-04 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
  • WN2897: MDW 2026-12-04 17:25:00 → BNA 2026-12-04 18:50:00; layover at BNA: 100 minutes.
  • WN4284: BNA 2026-12-04 20:30:00 → MIA 2026-12-04 23:50:00.

2026-11-27 → 2026-12-04 · Axel-exclusive $329.00

• Southwest Airlines WN4483 / WN2803: MIA 2026-11-27 06:50:00 → MDW 2026-11-27 12:05:00; 1 stop(s) via MCO; 375 minutes. Local airport times.
  • WN4483: MIA 2026-11-27 06:50:00 → MCO 2026-11-27 08:00:00; layover at MCO: 130 minutes.
  • WN2803: MCO 2026-11-27 10:10:00 → MDW 2026-11-27 12:05:00.
• Southwest Airlines WN2897 / WN4284: MDW 2026-12-04 17:25:00 → MIA 2026-12-04 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
  • WN2897: MDW 2026-12-04 17:25:00 → BNA 2026-12-04 18:50:00; layover at BNA: 100 minutes.
  • WN4284: BNA 2026-12-04 20:30:00 → MIA 2026-12-04 23:50:00.

2026-11-27 → 2026-12-04 · Axel-exclusive $329.00

• Southwest Airlines WN1194 / WN1718: MIA 2026-11-27 14:40:00 → MDW 2026-11-27 19:40:00; 1 stop(s) via CMH; 360 minutes. Local airport times.
  • WN1194: MIA 2026-11-27 14:40:00 → CMH 2026-11-27 17:20:00; layover at CMH: 130 minutes.
  • WN1718: CMH 2026-11-27 19:30:00 → MDW 2026-11-27 19:40:00.
• Southwest Airlines WN2897 / WN4284: MDW 2026-12-04 17:25:00 → MIA 2026-12-04 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
  • WN2897: MDW 2026-12-04 17:25:00 → BNA 2026-12-04 18:50:00; layover at BNA: 100 minutes.
  • WN4284: BNA 2026-12-04 20:30:00 → MIA 2026-12-04 23:50:00.

2026-11-27 → 2026-12-04 · Axel-exclusive $329.00

• Southwest Airlines WN3046 / WN3556: MIA 2026-11-27 15:05:00 → MDW 2026-11-27 20:10:00; 1 stop(s) via PIT; 365 minutes. Local airport times.
  • WN3046: MIA 2026-11-27 15:05:00 → PIT 2026-11-27 17:45:00; layover at PIT: 115 minutes.
  • WN3556: PIT 2026-11-27 19:40:00 → MDW 2026-11-27 20:10:00.
• Southwest Airlines WN2897 / WN4284: MDW 2026-12-04 17:25:00 → MIA 2026-12-04 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
  • WN2897: MDW 2026-12-04 17:25:00 → BNA 2026-12-04 18:50:00; layover at BNA: 100 minutes.
  • WN4284: BNA 2026-12-04 20:30:00 → MIA 2026-12-04 23:50:00.

2026-11-27 → 2026-12-04 · Axel-exclusive $349.25

• Southwest Airlines WN3081: MIA 2026-11-27 06:45:00 → MDW 2026-11-27 08:55:00; nonstop; 190 minutes. Local airport times.
• Southwest Airlines WN2897 / WN4284: MDW 2026-12-04 17:25:00 → MIA 2026-12-04 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
  • WN2897: MDW 2026-12-04 17:25:00 → BNA 2026-12-04 18:50:00; layover at BNA: 100 minutes.
  • WN4284: BNA 2026-12-04 20:30:00 → MIA 2026-12-04 23:50:00.

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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