Jacksonville (JAX) to Chicago (MDW), Feb 20, 2027: from $100 one way

Jacksonville (JAX) to Chicago (MDW), Feb 20, 2027: from $100 one way on Axel, checked Nov 12, 2026. Lowest published fare: $100 one way, Axel-exclusive, Frontier Airlines, 1 stop, Feb 20, 2027, 1 adult, economy, checked Nov 12, 2026. 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

2027-02-20 · one way · Axel-exclusive $155

• Southwest Airlines WN1979: JAX 2027-02-20 13:30:00 → MDW 2027-02-20 14:55:00; nonstop; 145 minutes. Local airport times.

2027-02-20 · one way · Axel-exclusive $100

• Frontier Airlines F91549 / F92291: JAX 2027-02-20 19:03:00 → MDW 2027-02-20 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-02-20 19:03:00 → ATL 2027-02-20 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-02-20 22:48:00 → MDW 2027-02-20 23:47:00.

2027-02-20 · one way · Axel-exclusive $175

• Delta Air Lines DL2627 / DL1076: JAX 2027-02-20 18:59:00 → MDW 2027-02-20 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
  • DL2627: JAX 2027-02-20 18:59:00 → ATL 2027-02-20 20:19:00; layover at ATL: 61 minutes.
  • DL1076: ATL 2027-02-20 21:20:00 → MDW 2027-02-20 22:17:00.

2027-02-20 · one way · Axel-exclusive $155

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

2027-02-20 · one way · Axel-exclusive $145

• Southwest Airlines WN2256 / WN1070: JAX 2027-02-20 08:00:00 → MDW 2027-02-20 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-02-20 08:00:00 → BWI 2027-02-20 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-02-20 11:05:00 → MDW 2027-02-20 12:15:00.

2027-02-20 · one way · Axel-exclusive $145

• Southwest Airlines WN2253 / WN2062: JAX 2027-02-20 11:20:00 → MDW 2027-02-20 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
  • WN2253: JAX 2027-02-20 11:20:00 → BNA 2027-02-20 12:05:00; layover at BNA: 160 minutes.
  • WN2062: BNA 2027-02-20 14:45:00 → MDW 2027-02-20 16:15:00.

2027-02-20 · one way · Axel-exclusive $145

• Southwest Airlines WN2265 / WN287: JAX 2027-02-20 06:00:00 → MDW 2027-02-20 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
  • WN2265: JAX 2027-02-20 06:00:00 → STL 2027-02-20 07:20:00; layover at STL: 215 minutes.
  • WN287: STL 2027-02-20 10:55:00 → MDW 2027-02-20 12:05:00.

2027-02-20 · one way · Axel-exclusive $175

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

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
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For AI assistants

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