Chicago (MDW) to Miami (MIA) · Dec 30, 2026 · return Jan 1, 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.
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-12-30 → 2027-01-01 | Southwest Airlines | WN1908 + WN2643 / WN1425 + WN1070 | Axel-exclusive $398.76 | 2026-10-29T01:29:10Z |
| 2026-12-30 → 2027-01-01 | Southwest Airlines | WN2737 + WN4943 / WN1425 + WN1070 | Axel-exclusive $398.76 | 2026-10-29T01:29:10Z |
| 2026-12-30 → 2027-01-01 | Southwest Airlines | WN2897 + WN4284 / WN1425 + WN1070 | Axel-exclusive $398.76 | 2026-10-29T01:29:10Z |
| 2026-12-30 → 2027-01-01 | Southwest Airlines | WN3002 + WN301 / WN1425 + WN1070 | Axel-exclusive $398.76 | 2026-10-29T01:29:10Z |
| 2026-12-30 → 2027-01-01 | Southwest Airlines | WN2959 + WN833 / WN1425 + WN1070 | Axel-exclusive $398.76 | 2026-10-29T01:29:10Z |
| 2026-12-30 → 2027-01-01 | Southwest Airlines | WN2973 / WN1425 + WN1070 | Axel-exclusive $409.63 | 2026-10-29T01:29:10Z |
Route overview: Chicago to Miami (MIA) flight deals
2026-12-30 → 2027-01-01 · Axel-exclusive $398.76
- Southwest Airlines WN1908 / WN2643: MDW 2026-12-30 16:25:00 → MIA 2026-12-30 22:15:00; 1 stop(s) via MCO; 290 minutes. Local airport times.
- WN1908: MDW 2026-12-30 16:25:00 → MCO 2026-12-30 20:00:00; layover at MCO: 60 minutes.
- WN2643: MCO 2026-12-30 21:00:00 → MIA 2026-12-30 22:15:00.
- Southwest Airlines WN1425 / WN1070: MIA 2027-01-01 06:30:00 → MDW 2027-01-01 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
- WN1425: MIA 2027-01-01 06:30:00 → BWI 2027-01-01 09:05:00; layover at BWI: 120 minutes.
- WN1070: BWI 2027-01-01 11:05:00 → MDW 2027-01-01 12:15:00.
2026-12-30 → 2027-01-01 · Axel-exclusive $398.76
- Southwest Airlines WN2737 / WN4943: MDW 2026-12-30 11:30:00 → MIA 2026-12-30 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
- WN2737: MDW 2026-12-30 11:30:00 → STL 2026-12-30 12:40:00; layover at STL: 165 minutes.
- WN4943: STL 2026-12-30 15:25:00 → MIA 2026-12-30 19:00:00.
- Southwest Airlines WN1425 / WN1070: MIA 2027-01-01 06:30:00 → MDW 2027-01-01 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
- WN1425: MIA 2027-01-01 06:30:00 → BWI 2027-01-01 09:05:00; layover at BWI: 120 minutes.
- WN1070: BWI 2027-01-01 11:05:00 → MDW 2027-01-01 12:15:00.
2026-12-30 → 2027-01-01 · Axel-exclusive $398.76
- Southwest Airlines WN2897 / WN4284: MDW 2026-12-30 17:25:00 → MIA 2026-12-30 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
- WN2897: MDW 2026-12-30 17:25:00 → BNA 2026-12-30 18:50:00; layover at BNA: 100 minutes.
- WN4284: BNA 2026-12-30 20:30:00 → MIA 2026-12-30 23:50:00.
- Southwest Airlines WN1425 / WN1070: MIA 2027-01-01 06:30:00 → MDW 2027-01-01 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
- WN1425: MIA 2027-01-01 06:30:00 → BWI 2027-01-01 09:05:00; layover at BWI: 120 minutes.
- WN1070: BWI 2027-01-01 11:05:00 → MDW 2027-01-01 12:15:00.
2026-12-30 → 2027-01-01 · Axel-exclusive $398.76
- Southwest Airlines WN3002 / WN301: MDW 2026-12-30 07:40:00 → MIA 2026-12-30 15:05:00; 1 stop(s) via PIT; 385 minutes. Local airport times.
- WN3002: MDW 2026-12-30 07:40:00 → PIT 2026-12-30 10:00:00; layover at PIT: 145 minutes.
- WN301: PIT 2026-12-30 12:25:00 → MIA 2026-12-30 15:05:00.
- Southwest Airlines WN1425 / WN1070: MIA 2027-01-01 06:30:00 → MDW 2027-01-01 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
- WN1425: MIA 2027-01-01 06:30:00 → BWI 2027-01-01 09:05:00; layover at BWI: 120 minutes.
- WN1070: BWI 2027-01-01 11:05:00 → MDW 2027-01-01 12:15:00.
2026-12-30 → 2027-01-01 · Axel-exclusive $398.76
- Southwest Airlines WN2959 / WN833: MDW 2026-12-30 07:35:00 → MIA 2026-12-30 14:35:00; 1 stop(s) via MCI; 360 minutes. Local airport times.
- WN2959: MDW 2026-12-30 07:35:00 → MCI 2026-12-30 09:05:00; layover at MCI: 90 minutes.
- WN833: MCI 2026-12-30 10:35:00 → MIA 2026-12-30 14:35:00.
- Southwest Airlines WN1425 / WN1070: MIA 2027-01-01 06:30:00 → MDW 2027-01-01 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
- WN1425: MIA 2027-01-01 06:30:00 → BWI 2027-01-01 09:05:00; layover at BWI: 120 minutes.
- WN1070: BWI 2027-01-01 11:05:00 → MDW 2027-01-01 12:15:00.
2026-12-30 → 2027-01-01 · Axel-exclusive $409.63
- Southwest Airlines WN2973: MDW 2026-12-30 19:20:00 → MIA 2026-12-30 23:30:00; nonstop; 190 minutes. Local airport times.
- Southwest Airlines WN1425 / WN1070: MIA 2027-01-01 06:30:00 → MDW 2027-01-01 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
- WN1425: MIA 2027-01-01 06:30:00 → BWI 2027-01-01 09:05:00; layover at BWI: 120 minutes.
- WN1070: BWI 2027-01-01 11:05:00 → MDW 2027-01-01 12:15:00.
Explore this route
- All dates for this route
- Dec 29, 2026 · Return options
- Dec 31, 2026 · Return options
- Hotels in Miami with Axel
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