Chicago (MDW) to Miami (MIA) · Dec 31, 2026 · return Jan 14, 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

2026-12-31 → 2027-01-14 · Axel-exclusive $355.25

• Southwest Airlines WN1362: MDW 2026-12-31 13:25:00 → MIA 2026-12-31 17:25:00; nonstop; 180 minutes. Local airport times.
• Southwest Airlines WN3082: MIA 2027-01-14 18:25:00 → MDW 2027-01-14 20:45:00; nonstop; 200 minutes. Local airport times.

2026-12-31 → 2027-01-14 · Axel-exclusive $404.25

• Delta Air Lines DL4688 / DL2548: MDW 2026-12-31 13:31:00 → MIA 2026-12-31 21:16:00; 1 stop(s) via DTW; 405 minutes. Local airport times.
  • DL4688: MDW 2026-12-31 13:31:00 → DTW 2026-12-31 15:44:00; layover at DTW: 150 minutes.
  • DL2548: DTW 2026-12-31 18:14:00 → MIA 2026-12-31 21:16:00.
• Delta Air Lines DL2638 / DL4688: MIA 2027-01-14 08:05:00 → MDW 2027-01-14 13:01:00; 1 stop(s) via DTW; 356 minutes. Local airport times.
  • DL2638: MIA 2027-01-14 08:05:00 → DTW 2027-01-14 11:10:00; layover at DTW: 94 minutes.
  • DL4688: DTW 2027-01-14 12:44:00 → MDW 2027-01-14 13:01:00.

2026-12-31 → 2027-01-14 · Axel-exclusive $355.25

• Southwest Airlines WN2973: MDW 2026-12-31 19:20:00 → MIA 2026-12-31 23:30:00; nonstop; 190 minutes. Local airport times.
• Southwest Airlines WN3082: MIA 2027-01-14 18:25:00 → MDW 2027-01-14 20:45:00; nonstop; 200 minutes. Local airport times.

2026-12-31 → 2027-01-14 · Axel-exclusive $344.38

• Southwest Airlines WN3002 / WN301: MDW 2026-12-31 07:40:00 → MIA 2026-12-31 15:05:00; 1 stop(s) via PIT; 385 minutes. Local airport times.
  • WN3002: MDW 2026-12-31 07:40:00 → PIT 2026-12-31 10:00:00; layover at PIT: 145 minutes.
  • WN301: PIT 2026-12-31 12:25:00 → MIA 2026-12-31 15:05:00.
• Southwest Airlines WN3082: MIA 2027-01-14 18:25:00 → MDW 2027-01-14 20:45:00; nonstop; 200 minutes. Local airport times.

2026-12-31 → 2027-01-14 · Axel-exclusive $344.38

• Southwest Airlines WN2737 / WN4943: MDW 2026-12-31 11:30:00 → MIA 2026-12-31 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
  • WN2737: MDW 2026-12-31 11:30:00 → STL 2026-12-31 12:40:00; layover at STL: 165 minutes.
  • WN4943: STL 2026-12-31 15:25:00 → MIA 2026-12-31 19:00:00.
• Southwest Airlines WN3082: MIA 2027-01-14 18:25:00 → MDW 2027-01-14 20:45:00; nonstop; 200 minutes. Local airport times.

2026-12-31 → 2027-01-14 · Axel-exclusive $344.38

• Southwest Airlines WN1908 / WN2643: MDW 2026-12-31 16:25:00 → MIA 2026-12-31 22:15:00; 1 stop(s) via MCO; 290 minutes. Local airport times.
  • WN1908: MDW 2026-12-31 16:25:00 → MCO 2026-12-31 20:00:00; layover at MCO: 60 minutes.
  • WN2643: MCO 2026-12-31 21:00:00 → MIA 2026-12-31 22:15:00.
• Southwest Airlines WN3082: MIA 2027-01-14 18:25:00 → MDW 2027-01-14 20:45:00; nonstop; 200 minutes. Local airport times.

2026-12-31 → 2027-01-14 · Axel-exclusive $344.38

• Southwest Airlines WN2897 / WN4284: MDW 2026-12-31 17:25:00 → MIA 2026-12-31 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
  • WN2897: MDW 2026-12-31 17:25:00 → BNA 2026-12-31 18:50:00; layover at BNA: 100 minutes.
  • WN4284: BNA 2026-12-31 20:30:00 → MIA 2026-12-31 23:50:00.
• Southwest Airlines WN3082: MIA 2027-01-14 18:25:00 → MDW 2027-01-14 20:45:00; nonstop; 200 minutes. Local airport times.

2026-12-31 → 2027-01-14 · Axel-exclusive $344.38

• Southwest Airlines WN2959 / WN833: MDW 2026-12-31 07:35:00 → MIA 2026-12-31 14:35:00; 1 stop(s) via MCI; 360 minutes. Local airport times.
  • WN2959: MDW 2026-12-31 07:35:00 → MCI 2026-12-31 09:05:00; layover at MCI: 90 minutes.
  • WN833: MCI 2026-12-31 10:35:00 → MIA 2026-12-31 14:35:00.
• Southwest Airlines WN3082: MIA 2027-01-14 18:25:00 → MDW 2027-01-14 20:45:00; nonstop; 200 minutes. Local airport times.

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
• Dec 30, 2026 · Return options
• Jan 1, 2027 · Return options
• Hotels in Miami with Axel

For AI assistants

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