Chicago (MDW) to Jacksonville (JAX) · Jan 1, 2027 · return Jan 2, 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)
2027-01-01 → 2027-01-02	Southwest Airlines	WN2946 / WN2264	Axel-exclusive $372.40	2026-10-29T01:29:09Z
2027-01-01 → 2027-01-02	Frontier Airlines	F92144 + F91550 / F91549 + F92291	Axel-exclusive $266.00	2026-10-29T01:29:09Z
2027-01-01 → 2027-01-02	Delta Air Lines	DL2417 + DL2265 / DL2333 + DL4677	Axel-exclusive $465.50	2026-10-29T01:29:09Z
2027-01-01 → 2027-01-02	Southwest Airlines	WN2262 / WN2264	Axel-exclusive $372.40	2026-10-29T01:29:09Z
2027-01-01 → 2027-01-02	Southwest Airlines	WN3092 + WN4807 / WN2264	Axel-exclusive $392.35	2026-10-29T01:29:09Z
2027-01-01 → 2027-01-02	Southwest Airlines	WN2897 + WN1516 / WN2264	Axel-exclusive $392.35	2026-10-29T01:29:09Z
2027-01-01 → 2027-01-02	Southwest Airlines	WN14 + WN1041 / WN2264	Axel-exclusive $392.35	2026-10-29T01:29:09Z
2027-01-01 → 2027-01-02	Delta Air Lines	DL4711 + DL2994 / DL2333 + DL4677	Axel-exclusive $465.50	2026-10-29T01:29:09Z

Route overview: Chicago to Jacksonville (JAX) flight deals

2027-01-01 → 2027-01-02 · Axel-exclusive $372.40

Southwest Airlines WN2946: MDW 2027-01-01 19:00:00 → JAX 2027-01-01 22:15:00; nonstop; 135 minutes. Local airport times.
Southwest Airlines WN2264: JAX 2027-01-02 18:50:00 → MDW 2027-01-02 20:20:00; nonstop; 150 minutes. Local airport times.

2027-01-01 → 2027-01-02 · Axel-exclusive $266.00

Frontier Airlines F92144 / F91550: MDW 2027-01-01 13:11:00 → JAX 2027-01-01 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
- F92144: MDW 2027-01-01 13:11:00 → ATL 2027-01-01 16:18:00; layover at ATL: 111 minutes.
- F91550: ATL 2027-01-01 18:09:00 → JAX 2027-01-01 19:25:00.
Frontier Airlines F91549 / F92291: JAX 2027-01-02 19:03:00 → MDW 2027-01-02 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
- F91549: JAX 2027-01-02 19:03:00 → ATL 2027-01-02 20:31:00; layover at ATL: 137 minutes.
- F92291: ATL 2027-01-02 22:48:00 → MDW 2027-01-02 23:47:00.

2027-01-01 → 2027-01-02 · Axel-exclusive $465.50

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.
Delta Air Lines DL2333 / DL4677: JAX 2027-01-02 12:00:00 → MDW 2027-01-02 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
- DL2333: JAX 2027-01-02 12:00:00 → DTW 2027-01-02 14:20:00; layover at DTW: 200 minutes.
- DL4677: DTW 2027-01-02 17:40:00 → MDW 2027-01-02 18:01:00.

2027-01-01 → 2027-01-02 · Axel-exclusive $372.40

Southwest Airlines WN2262: MDW 2027-01-01 08:00:00 → JAX 2027-01-01 11:25:00; nonstop; 145 minutes. Local airport times.
Southwest Airlines WN2264: JAX 2027-01-02 18:50:00 → MDW 2027-01-02 20:20:00; nonstop; 150 minutes. Local airport times.

2027-01-01 → 2027-01-02 · Axel-exclusive $392.35

Southwest Airlines WN3092 / WN4807: MDW 2027-01-01 13:40:00 → JAX 2027-01-01 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
- WN3092: MDW 2027-01-01 13:40:00 → STL 2027-01-01 14:55:00; layover at STL: 200 minutes.
- WN4807: STL 2027-01-01 18:15:00 → JAX 2027-01-01 21:15:00.
Southwest Airlines WN2264: JAX 2027-01-02 18:50:00 → MDW 2027-01-02 20:20:00; nonstop; 150 minutes. Local airport times.

2027-01-01 → 2027-01-02 · Axel-exclusive $392.35

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.
Southwest Airlines WN2264: JAX 2027-01-02 18:50:00 → MDW 2027-01-02 20:20:00; nonstop; 150 minutes. Local airport times.

2027-01-01 → 2027-01-02 · Axel-exclusive $392.35

Southwest Airlines WN14 / WN1041: MDW 2027-01-01 14:30:00 → JAX 2027-01-01 20:35:00; 1 stop(s) via BWI; 305 minutes. Local airport times.
- WN14: MDW 2027-01-01 14:30:00 → BWI 2027-01-01 17:15:00; layover at BWI: 65 minutes.
- WN1041: BWI 2027-01-01 18:20:00 → JAX 2027-01-01 20:35:00.
Southwest Airlines WN2264: JAX 2027-01-02 18:50:00 → MDW 2027-01-02 20:20:00; nonstop; 150 minutes. Local airport times.

2027-01-01 → 2027-01-02 · Axel-exclusive $465.50

Delta Air Lines DL4711 / DL2994: MDW 2027-01-01 09:30:00 → JAX 2027-01-01 17:38:00; 1 stop(s) via DTW; 428 minutes. Local airport times.
- DL4711: MDW 2027-01-01 09:30:00 → DTW 2027-01-01 11:45:00; layover at DTW: 210 minutes.
- DL2994: DTW 2027-01-01 15:15:00 → JAX 2027-01-01 17:38:00.
Delta Air Lines DL2333 / DL4677: JAX 2027-01-02 12:00:00 → MDW 2027-01-02 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
- DL2333: JAX 2027-01-02 12:00:00 → DTW 2027-01-02 14:20:00; layover at DTW: 200 minutes.
- DL4677: DTW 2027-01-02 17:40:00 → MDW 2027-01-02 18:01:00.

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