Jacksonville (JAX) to Chicago (MDW) · Dec 25, 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) |
|---|---|---|---|---|
| 2026-12-25 → 2027-01-01 | Southwest Airlines | WN1979 / WN2262 | Axel-exclusive $381.35 | 2026-10-29T01:16:41Z |
| 2026-12-25 → 2027-01-01 | Delta Air Lines | DL2333 + DL4677 / DL2417 + DL2265 | Axel-exclusive $433.95 | 2026-10-29T01:16:41Z |
| 2026-12-25 → 2027-01-01 | Southwest Airlines | WN2264 / WN2262 | Axel-exclusive $381.35 | 2026-10-29T01:16:41Z |
| 2026-12-25 → 2027-01-01 | Southwest Airlines | WN2256 + WN1070 / WN2262 | Axel-exclusive $371.23 | 2026-10-29T01:16:41Z |
| 2026-12-25 → 2027-01-01 | Southwest Airlines | WN2265 + WN287 / WN2262 | Axel-exclusive $371.23 | 2026-10-29T01:16:41Z |
| 2026-12-25 → 2027-01-01 | Southwest Airlines | WN2253 + WN2062 / WN2262 | Axel-exclusive $371.23 | 2026-10-29T01:16:41Z |
| 2026-12-25 → 2027-01-01 | Southwest Airlines | WN2264 / WN2897 + WN1516 | Axel-exclusive $371.75 | 2026-10-29T01:16:41Z |
| 2026-12-25 → 2027-01-01 | Delta Air Lines | DL2627 + DL1076 / DL2417 + DL2265 | Axel-exclusive $433.95 | 2026-10-29T01:16:41Z |
Route overview: Jacksonville to Chicago (MDW) flight deals
2026-12-25 → 2027-01-01 · Axel-exclusive $381.35
- Southwest Airlines WN1979: JAX 2026-12-25 13:30:00 → MDW 2026-12-25 14:55:00; nonstop; 145 minutes. Local airport times.
- Southwest Airlines WN2262: MDW 2027-01-01 08:00:00 → JAX 2027-01-01 11:25:00; nonstop; 145 minutes. Local airport times.
2026-12-25 → 2027-01-01 · Axel-exclusive $433.95
- Delta Air Lines DL2333 / DL4677: JAX 2026-12-25 12:00:00 → MDW 2026-12-25 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
- DL2333: JAX 2026-12-25 12:00:00 → DTW 2026-12-25 14:20:00; layover at DTW: 200 minutes.
- DL4677: DTW 2026-12-25 17:40:00 → MDW 2026-12-25 18:01:00.
- Delta Air Lines DL2417 / DL2265: MDW 2027-01-01 13:02:00 → JAX 2027-01-01 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
- DL2417: MDW 2027-01-01 13:02:00 → ATL 2027-01-01 16:01:00; layover at ATL: 212 minutes.
- DL2265: ATL 2027-01-01 19:33:00 → JAX 2027-01-01 20:43:00.
2026-12-25 → 2027-01-01 · Axel-exclusive $381.35
- Southwest Airlines WN2264: JAX 2026-12-25 18:55:00 → MDW 2026-12-25 20:20:00; nonstop; 145 minutes. Local airport times.
- Southwest Airlines WN2262: MDW 2027-01-01 08:00:00 → JAX 2027-01-01 11:25:00; nonstop; 145 minutes. Local airport times.
2026-12-25 → 2027-01-01 · Axel-exclusive $371.23
- Southwest Airlines WN2256 / WN1070: JAX 2026-12-25 08:00:00 → MDW 2026-12-25 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
- WN2256: JAX 2026-12-25 08:00:00 → BWI 2026-12-25 09:50:00; layover at BWI: 75 minutes.
- WN1070: BWI 2026-12-25 11:05:00 → MDW 2026-12-25 12:15:00.
- Southwest Airlines WN2262: MDW 2027-01-01 08:00:00 → JAX 2027-01-01 11:25:00; nonstop; 145 minutes. Local airport times.
2026-12-25 → 2027-01-01 · Axel-exclusive $371.23
- Southwest Airlines WN2265 / WN287: JAX 2026-12-25 06:00:00 → MDW 2026-12-25 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
- WN2265: JAX 2026-12-25 06:00:00 → STL 2026-12-25 07:20:00; layover at STL: 215 minutes.
- WN287: STL 2026-12-25 10:55:00 → MDW 2026-12-25 12:05:00.
- Southwest Airlines WN2262: MDW 2027-01-01 08:00:00 → JAX 2027-01-01 11:25:00; nonstop; 145 minutes. Local airport times.
2026-12-25 → 2027-01-01 · Axel-exclusive $371.23
- Southwest Airlines WN2253 / WN2062: JAX 2026-12-25 11:20:00 → MDW 2026-12-25 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
- WN2253: JAX 2026-12-25 11:20:00 → BNA 2026-12-25 12:05:00; layover at BNA: 160 minutes.
- WN2062: BNA 2026-12-25 14:45:00 → MDW 2026-12-25 16:15:00.
- Southwest Airlines WN2262: MDW 2027-01-01 08:00:00 → JAX 2027-01-01 11:25:00; nonstop; 145 minutes. Local airport times.
2026-12-25 → 2027-01-01 · Axel-exclusive $371.75
- Southwest Airlines WN2264: JAX 2026-12-25 18:50:00 → MDW 2026-12-25 20:20:00; nonstop; 150 minutes. Local airport times.
- Southwest Airlines WN2897 / WN1516: MDW 2027-01-01 17:25:00 → JAX 2027-01-01 23:45:00; 1 stop(s) via BNA; 320 minutes. Local airport times.
- WN2897: MDW 2027-01-01 17:25:00 → BNA 2027-01-01 18:50:00; layover at BNA: 140 minutes.
- WN1516: BNA 2027-01-01 21:10:00 → JAX 2027-01-01 23:45:00.
2026-12-25 → 2027-01-01 · Axel-exclusive $433.95
- Delta Air Lines DL2627 / DL1076: JAX 2026-12-25 18:59:00 → MDW 2026-12-25 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
- DL2627: JAX 2026-12-25 18:59:00 → ATL 2026-12-25 20:19:00; layover at ATL: 61 minutes.
- DL1076: ATL 2026-12-25 21:20:00 → MDW 2026-12-25 22:17:00.
- Delta Air Lines DL2417 / DL2265: MDW 2027-01-01 13:02:00 → JAX 2027-01-01 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
- DL2417: MDW 2027-01-01 13:02:00 → ATL 2027-01-01 16:01:00; layover at ATL: 212 minutes.
- DL2265: ATL 2027-01-01 19:33:00 → JAX 2027-01-01 20:43:00.
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