Jacksonville (JAX) to Chicago (MDW) · May 27, 2027 · return May 30, 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.

Route overview: Jacksonville to Chicago (MDW) flight deals

2027-05-27 → 2027-05-30 · Axel-exclusive $344.00

• Southwest Airlines WN2256 / WN1070: JAX 2027-05-27 08:00:00 → MDW 2027-05-27 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-05-27 08:00:00 → BWI 2027-05-27 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-05-27 11:05:00 → MDW 2027-05-27 12:15:00.
• Southwest Airlines WN3092 / WN4807: MDW 2027-05-30 13:40:00 → JAX 2027-05-30 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
  • WN3092: MDW 2027-05-30 13:40:00 → STL 2027-05-30 14:55:00; layover at STL: 200 minutes.
  • WN4807: STL 2027-05-30 18:15:00 → JAX 2027-05-30 21:15:00.

2027-05-27 → 2027-05-30 · Axel-exclusive $397.75

• Delta Air Lines DL2333 / DL4677: JAX 2027-05-27 12:00:00 → MDW 2027-05-27 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
  • DL2333: JAX 2027-05-27 12:00:00 → DTW 2027-05-27 14:20:00; layover at DTW: 200 minutes.
  • DL4677: DTW 2027-05-27 17:40:00 → MDW 2027-05-27 18:01:00.
• Delta Air Lines DL2417 / DL2265: MDW 2027-05-30 13:02:00 → JAX 2027-05-30 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
  • DL2417: MDW 2027-05-30 13:02:00 → ATL 2027-05-30 16:01:00; layover at ATL: 212 minutes.
  • DL2265: ATL 2027-05-30 19:33:00 → JAX 2027-05-30 20:43:00.

2027-05-27 → 2027-05-30 · Axel-exclusive $344.00

• Southwest Airlines WN2253 / WN2062: JAX 2027-05-27 11:20:00 → MDW 2027-05-27 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
  • WN2253: JAX 2027-05-27 11:20:00 → BNA 2027-05-27 12:05:00; layover at BNA: 160 minutes.
  • WN2062: BNA 2027-05-27 14:45:00 → MDW 2027-05-27 16:15:00.
• Southwest Airlines WN3092 / WN4807: MDW 2027-05-30 13:40:00 → JAX 2027-05-30 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
  • WN3092: MDW 2027-05-30 13:40:00 → STL 2027-05-30 14:55:00; layover at STL: 200 minutes.
  • WN4807: STL 2027-05-30 18:15:00 → JAX 2027-05-30 21:15:00.

2027-05-27 → 2027-05-30 · Axel-exclusive $344.00

• Southwest Airlines WN2265 / WN287: JAX 2027-05-27 06:00:00 → MDW 2027-05-27 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
  • WN2265: JAX 2027-05-27 06:00:00 → STL 2027-05-27 07:20:00; layover at STL: 215 minutes.
  • WN287: STL 2027-05-27 10:55:00 → MDW 2027-05-27 12:05:00.
• Southwest Airlines WN3092 / WN4807: MDW 2027-05-30 13:40:00 → JAX 2027-05-30 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
  • WN3092: MDW 2027-05-30 13:40:00 → STL 2027-05-30 14:55:00; layover at STL: 200 minutes.
  • WN4807: STL 2027-05-30 18:15:00 → JAX 2027-05-30 21:15:00.

2027-05-27 → 2027-05-30 · Axel-exclusive $354.00

• Southwest Airlines WN2264: JAX 2027-05-27 18:50:00 → MDW 2027-05-27 20:20:00; nonstop; 150 minutes. Local airport times.
• Southwest Airlines WN3092 / WN4807: MDW 2027-05-30 13:40:00 → JAX 2027-05-30 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
  • WN3092: MDW 2027-05-30 13:40:00 → STL 2027-05-30 14:55:00; layover at STL: 200 minutes.
  • WN4807: STL 2027-05-30 18:15:00 → JAX 2027-05-30 21:15:00.

2027-05-27 → 2027-05-30 · Axel-exclusive $397.75

• Delta Air Lines DL2627 / DL1076: JAX 2027-05-27 18:59:00 → MDW 2027-05-27 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
  • DL2627: JAX 2027-05-27 18:59:00 → ATL 2027-05-27 20:19:00; layover at ATL: 61 minutes.
  • DL1076: ATL 2027-05-27 21:20:00 → MDW 2027-05-27 22:17:00.
• Delta Air Lines DL2417 / DL2265: MDW 2027-05-30 13:02:00 → JAX 2027-05-30 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
  • DL2417: MDW 2027-05-30 13:02:00 → ATL 2027-05-30 16:01:00; layover at ATL: 212 minutes.
  • DL2265: ATL 2027-05-30 19:33:00 → JAX 2027-05-30 20:43:00.

Explore this route

• All dates for this route
• May 26, 2027 · Return options
• May 28, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Jacksonville (JAX) to Chicago (MDW) · May 27, 2027 · return May 30, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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