Jacksonville (JAX) to Chicago (MDW) · Jan 4, 2027 · return Jan 5, 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)
2027-01-04 → 2027-01-05	Southwest Airlines	WN1979 / WN2946	Axel-exclusive $275.50	2026-10-29T01:16:41Z
2027-01-04 → 2027-01-05	Frontier Airlines	F91549 + F92291 / F92144 + F91550	Axel-exclusive $175.76	2026-10-29T01:16:41Z
2027-01-04 → 2027-01-05	Delta Air Lines	DL2333 + DL4677 / DL2417 + DL2265	Axel-exclusive $313.50	2026-10-29T01:16:41Z
2027-01-04 → 2027-01-05	Southwest Airlines	WN2264 / WN2946	Axel-exclusive $275.50	2026-10-29T01:16:41Z
2027-01-04 → 2027-01-05	Southwest Airlines	WN2265 + WN287 / WN2946	Axel-exclusive $268.38	2026-10-29T01:16:41Z
2027-01-04 → 2027-01-05	Southwest Airlines	WN2256 + WN1070 / WN2946	Axel-exclusive $268.38	2026-10-29T01:16:41Z
2027-01-04 → 2027-01-05	Southwest Airlines	WN2253 + WN2062 / WN2946	Axel-exclusive $268.38	2026-10-29T01:16:41Z
2027-01-04 → 2027-01-05	Delta Air Lines	DL2627 + DL1076 / DL2417 + DL2265	Axel-exclusive $313.50	2026-10-29T01:16:41Z

Route overview: Jacksonville to Chicago (MDW) flight deals

2027-01-04 → 2027-01-05 · Axel-exclusive $275.50

Southwest Airlines WN1979: JAX 2027-01-04 13:30:00 → MDW 2027-01-04 14:55:00; nonstop; 145 minutes. Local airport times.
Southwest Airlines WN2946: MDW 2027-01-05 19:00:00 → JAX 2027-01-05 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-04 → 2027-01-05 · Axel-exclusive $175.76

Frontier Airlines F91549 / F92291: JAX 2027-01-04 19:03:00 → MDW 2027-01-04 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
- F91549: JAX 2027-01-04 19:03:00 → ATL 2027-01-04 20:31:00; layover at ATL: 137 minutes.
- F92291: ATL 2027-01-04 22:48:00 → MDW 2027-01-04 23:47:00.
Frontier Airlines F92144 / F91550: MDW 2027-01-05 13:11:00 → JAX 2027-01-05 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
- F92144: MDW 2027-01-05 13:11:00 → ATL 2027-01-05 16:18:00; layover at ATL: 111 minutes.
- F91550: ATL 2027-01-05 18:09:00 → JAX 2027-01-05 19:25:00.

2027-01-04 → 2027-01-05 · Axel-exclusive $313.50

Delta Air Lines DL2333 / DL4677: JAX 2027-01-04 12:00:00 → MDW 2027-01-04 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
- DL2333: JAX 2027-01-04 12:00:00 → DTW 2027-01-04 14:20:00; layover at DTW: 200 minutes.
- DL4677: DTW 2027-01-04 17:40:00 → MDW 2027-01-04 18:01:00.
Delta Air Lines DL2417 / DL2265: MDW 2027-01-05 13:02:00 → JAX 2027-01-05 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
- DL2417: MDW 2027-01-05 13:02:00 → ATL 2027-01-05 16:01:00; layover at ATL: 212 minutes.
- DL2265: ATL 2027-01-05 19:33:00 → JAX 2027-01-05 20:43:00.

2027-01-04 → 2027-01-05 · Axel-exclusive $275.50

Southwest Airlines WN2264: JAX 2027-01-04 18:55:00 → MDW 2027-01-04 20:20:00; nonstop; 145 minutes. Local airport times.
Southwest Airlines WN2946: MDW 2027-01-05 19:00:00 → JAX 2027-01-05 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-04 → 2027-01-05 · Axel-exclusive $268.38

Southwest Airlines WN2265 / WN287: JAX 2027-01-04 06:00:00 → MDW 2027-01-04 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
- WN2265: JAX 2027-01-04 06:00:00 → STL 2027-01-04 07:20:00; layover at STL: 215 minutes.
- WN287: STL 2027-01-04 10:55:00 → MDW 2027-01-04 12:05:00.
Southwest Airlines WN2946: MDW 2027-01-05 19:00:00 → JAX 2027-01-05 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-04 → 2027-01-05 · Axel-exclusive $268.38

Southwest Airlines WN2256 / WN1070: JAX 2027-01-04 08:00:00 → MDW 2027-01-04 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
- WN2256: JAX 2027-01-04 08:00:00 → BWI 2027-01-04 09:50:00; layover at BWI: 75 minutes.
- WN1070: BWI 2027-01-04 11:05:00 → MDW 2027-01-04 12:15:00.
Southwest Airlines WN2946: MDW 2027-01-05 19:00:00 → JAX 2027-01-05 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-04 → 2027-01-05 · Axel-exclusive $268.38

Southwest Airlines WN2253 / WN2062: JAX 2027-01-04 11:20:00 → MDW 2027-01-04 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
- WN2253: JAX 2027-01-04 11:20:00 → BNA 2027-01-04 12:05:00; layover at BNA: 160 minutes.
- WN2062: BNA 2027-01-04 14:45:00 → MDW 2027-01-04 16:15:00.
Southwest Airlines WN2946: MDW 2027-01-05 19:00:00 → JAX 2027-01-05 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-04 → 2027-01-05 · Axel-exclusive $313.50

Delta Air Lines DL2627 / DL1076: JAX 2027-01-04 18:59:00 → MDW 2027-01-04 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
- DL2627: JAX 2027-01-04 18:59:00 → ATL 2027-01-04 20:19:00; layover at ATL: 61 minutes.
- DL1076: ATL 2027-01-04 21:20:00 → MDW 2027-01-04 22:17:00.
Delta Air Lines DL2417 / DL2265: MDW 2027-01-05 13:02:00 → JAX 2027-01-05 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
- DL2417: MDW 2027-01-05 13:02:00 → ATL 2027-01-05 16:01:00; layover at ATL: 212 minutes.
- DL2265: ATL 2027-01-05 19:33:00 → JAX 2027-01-05 20:43:00.

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