Miami (MIA) to Chicago (MDW) · Dec 26, 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) |
|---|---|---|---|---|
| 2026-12-26 → 2027-01-01 | Southwest Airlines | WN3046 + WN3556 / WN2897 + WN4284 | Axel-exclusive $385.00 | 2026-10-29T01:29:41Z |
| 2026-12-26 → 2027-01-01 | Delta Air Lines | DL2638 + DL4688 / DL4688 + DL2548 | Axel-exclusive $474.38 | 2026-10-29T01:29:41Z |
| 2026-12-26 → 2027-01-01 | Southwest Airlines | WN1194 + WN1718 / WN2897 + WN4284 | Axel-exclusive $385.00 | 2026-10-29T01:29:41Z |
| 2026-12-26 → 2027-01-01 | Southwest Airlines | WN4483 + WN2803 / WN2897 + WN4284 | Axel-exclusive $385.00 | 2026-10-29T01:29:41Z |
| 2026-12-26 → 2027-01-01 | Southwest Airlines | WN1425 + WN1070 / WN2897 + WN4284 | Axel-exclusive $385.00 | 2026-10-29T01:29:41Z |
| 2026-12-26 → 2027-01-01 | Southwest Airlines | WN2466 / WN2897 + WN4284 | Axel-exclusive $406.00 | 2026-10-29T01:29:41Z |
Route overview: Miami or Fort Lauderdale to Chicago (MDW) flight deals
2026-12-26 → 2027-01-01 · Axel-exclusive $385.00
- Southwest Airlines WN3046 / WN3556: MIA 2026-12-26 15:05:00 → MDW 2026-12-26 20:10:00; 1 stop(s) via PIT; 365 minutes. Local airport times.
- WN3046: MIA 2026-12-26 15:05:00 → PIT 2026-12-26 17:45:00; layover at PIT: 115 minutes.
- WN3556: PIT 2026-12-26 19:40:00 → MDW 2026-12-26 20:10:00.
- Southwest Airlines WN2897 / WN4284: MDW 2027-01-01 17:25:00 → MIA 2027-01-01 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
- WN2897: MDW 2027-01-01 17:25:00 → BNA 2027-01-01 18:50:00; layover at BNA: 100 minutes.
- WN4284: BNA 2027-01-01 20:30:00 → MIA 2027-01-01 23:50:00.
2026-12-26 → 2027-01-01 · Axel-exclusive $474.38
- Delta Air Lines DL2638 / DL4688: MIA 2026-12-26 08:05:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 356 minutes. Local airport times.
- DL2638: MIA 2026-12-26 08:05:00 → DTW 2026-12-26 11:10:00; layover at DTW: 94 minutes.
- DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
- Delta Air Lines DL4688 / DL2548: MDW 2027-01-01 13:31:00 → MIA 2027-01-01 21:16:00; 1 stop(s) via DTW; 405 minutes. Local airport times.
- DL4688: MDW 2027-01-01 13:31:00 → DTW 2027-01-01 15:44:00; layover at DTW: 150 minutes.
- DL2548: DTW 2027-01-01 18:14:00 → MIA 2027-01-01 21:16:00.
2026-12-26 → 2027-01-01 · Axel-exclusive $385.00
- Southwest Airlines WN1194 / WN1718: MIA 2026-12-26 14:40:00 → MDW 2026-12-26 19:40:00; 1 stop(s) via CMH; 360 minutes. Local airport times.
- WN1194: MIA 2026-12-26 14:40:00 → CMH 2026-12-26 17:20:00; layover at CMH: 130 minutes.
- WN1718: CMH 2026-12-26 19:30:00 → MDW 2026-12-26 19:40:00.
- Southwest Airlines WN2897 / WN4284: MDW 2027-01-01 17:25:00 → MIA 2027-01-01 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
- WN2897: MDW 2027-01-01 17:25:00 → BNA 2027-01-01 18:50:00; layover at BNA: 100 minutes.
- WN4284: BNA 2027-01-01 20:30:00 → MIA 2027-01-01 23:50:00.
2026-12-26 → 2027-01-01 · Axel-exclusive $385.00
- Southwest Airlines WN4483 / WN2803: MIA 2026-12-26 06:50:00 → MDW 2026-12-26 12:05:00; 1 stop(s) via MCO; 375 minutes. Local airport times.
- WN4483: MIA 2026-12-26 06:50:00 → MCO 2026-12-26 08:00:00; layover at MCO: 130 minutes.
- WN2803: MCO 2026-12-26 10:10:00 → MDW 2026-12-26 12:05:00.
- Southwest Airlines WN2897 / WN4284: MDW 2027-01-01 17:25:00 → MIA 2027-01-01 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
- WN2897: MDW 2027-01-01 17:25:00 → BNA 2027-01-01 18:50:00; layover at BNA: 100 minutes.
- WN4284: BNA 2027-01-01 20:30:00 → MIA 2027-01-01 23:50:00.
2026-12-26 → 2027-01-01 · Axel-exclusive $385.00
- Southwest Airlines WN1425 / WN1070: MIA 2026-12-26 06:30:00 → MDW 2026-12-26 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
- WN1425: MIA 2026-12-26 06:30:00 → BWI 2026-12-26 09:05:00; layover at BWI: 120 minutes.
- WN1070: BWI 2026-12-26 11:05:00 → MDW 2026-12-26 12:15:00.
- Southwest Airlines WN2897 / WN4284: MDW 2027-01-01 17:25:00 → MIA 2027-01-01 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
- WN2897: MDW 2027-01-01 17:25:00 → BNA 2027-01-01 18:50:00; layover at BNA: 100 minutes.
- WN4284: BNA 2027-01-01 20:30:00 → MIA 2027-01-01 23:50:00.
2026-12-26 → 2027-01-01 · Axel-exclusive $406.00
- Southwest Airlines WN2466: MIA 2026-12-26 15:00:00 → MDW 2026-12-26 17:10:00; nonstop; 190 minutes. Local airport times.
- Southwest Airlines WN2897 / WN4284: MDW 2027-01-01 17:25:00 → MIA 2027-01-01 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
- WN2897: MDW 2027-01-01 17:25:00 → BNA 2027-01-01 18:50:00; layover at BNA: 100 minutes.
- WN4284: BNA 2027-01-01 20:30:00 → MIA 2027-01-01 23:50:00.
Explore this route
- All dates for this route
- Dec 25, 2026 · Return options
- Dec 27, 2026 · Return options
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