Orlando (MCO) to Chicago (MDW), Dec 25–27, 2026: from $123 one way

Orlando (MCO) to Chicago (MDW), Dec 25–27, 2026: from $123 one way on Axel, checked Oct 29, 2026. Lowest published fare: $123 one way, Axel-exclusive, Frontier Airlines, nonstop, Dec 25, 2026, 1 adult, economy, checked Oct 29, 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: Orlando to Chicago (MDW) flight deals

2026-12-25 · one way · Axel-exclusive $123.25

• Frontier Airlines F91457: MCO 2026-12-25 17:29:00 → MDW 2026-12-25 19:30:00; nonstop; 181 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $195.75

• Southwest Airlines WN2803: MCO 2026-12-27 10:10:00 → MDW 2026-12-27 12:05:00; nonstop; 175 minutes. Local airport times.

2026-12-26 · one way · Axel-exclusive $253.75

• Delta Air Lines DL1150 / DL1076: MCO 2026-12-26 17:45:00 → MDW 2026-12-26 22:17:00; 1 stop(s) via ATL; 332 minutes. Local airport times.
  • DL1150: MCO 2026-12-26 17:45:00 → ATL 2026-12-26 19:25:00; layover at ATL: 115 minutes.
  • DL1076: ATL 2026-12-26 21:20:00 → MDW 2026-12-26 22:17:00.

2026-12-27 · one way · Axel-exclusive $123.25

• Frontier Airlines F91457: MCO 2026-12-27 17:29:00 → MDW 2026-12-27 19:30:00; nonstop; 181 minutes. Local airport times.

2026-12-26 · one way · Axel-exclusive $123.25

• Frontier Airlines F91457: MCO 2026-12-26 17:29:00 → MDW 2026-12-26 19:30:00; nonstop; 181 minutes. Local airport times.

2026-12-26 · one way · Axel-exclusive $195.75

• Southwest Airlines WN2805: MCO 2026-12-26 16:35:00 → MDW 2026-12-26 18:30:00; nonstop; 175 minutes. Local airport times.

2026-12-25 · one way · Axel-exclusive $195.75

• Southwest Airlines WN2803: MCO 2026-12-25 10:10:00 → MDW 2026-12-25 12:05:00; nonstop; 175 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $195.75

• Southwest Airlines WN2805: MCO 2026-12-27 17:00:00 → MDW 2026-12-27 18:55:00; nonstop; 175 minutes. Local airport times.

2026-12-25 · one way · Axel-exclusive $195.75

• Southwest Airlines WN2805: MCO 2026-12-25 16:35:00 → MDW 2026-12-25 18:30:00; nonstop; 175 minutes. Local airport times.

2026-12-26 · one way · Axel-exclusive $195.75

• Southwest Airlines WN2803: MCO 2026-12-26 10:10:00 → MDW 2026-12-26 12:05:00; nonstop; 175 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $159.50

• Frontier Airlines F91563 / F92779: MCO 2026-12-27 07:10:00 → MDW 2026-12-27 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
  • F91563: MCO 2026-12-27 07:10:00 → ATL 2026-12-27 09:14:00; layover at ATL: 73 minutes.
  • F92779: ATL 2026-12-27 10:27:00 → MDW 2026-12-27 11:33:00.

2026-12-25 · one way · Axel-exclusive $159.50

• Frontier Airlines F91563 / F92779: MCO 2026-12-25 07:10:00 → MDW 2026-12-25 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
  • F91563: MCO 2026-12-25 07:10:00 → ATL 2026-12-25 09:14:00; layover at ATL: 73 minutes.
  • F92779: ATL 2026-12-25 10:27:00 → MDW 2026-12-25 11:33:00.

2026-12-26 · one way · Axel-exclusive $159.50

• Frontier Airlines F91563 / F92779: MCO 2026-12-26 07:10:00 → MDW 2026-12-26 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
  • F91563: MCO 2026-12-26 07:10:00 → ATL 2026-12-26 09:14:00; layover at ATL: 73 minutes.
  • F92779: ATL 2026-12-26 10:27:00 → MDW 2026-12-26 11:33:00.

2026-12-27 · one way · Axel-exclusive $210.25

• Southwest Airlines WN1915 / WN282: MCO 2026-12-27 15:40:00 → MDW 2026-12-27 19:50:00; 1 stop(s) via SDF; 310 minutes. Local airport times.
  • WN1915: MCO 2026-12-27 15:40:00 → SDF 2026-12-27 18:00:00; layover at SDF: 95 minutes.
  • WN282: SDF 2026-12-27 19:35:00 → MDW 2026-12-27 19:50:00.

2026-12-27 · one way · Axel-exclusive $210.25

• Southwest Airlines WN2777 / WN2106: MCO 2026-12-27 10:40:00 → MDW 2026-12-27 15:00:00; 1 stop(s) via RSW; 320 minutes. Local airport times.
  • WN2777: MCO 2026-12-27 10:40:00 → RSW 2026-12-27 11:45:00; layover at RSW: 80 minutes.
  • WN2106: RSW 2026-12-27 13:05:00 → MDW 2026-12-27 15:00:00.

2026-12-27 · one way · Axel-exclusive $210.25

• Southwest Airlines WN1789 / WN287: MCO 2026-12-27 08:10:00 → MDW 2026-12-27 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN1789: MCO 2026-12-27 08:10:00 → STL 2026-12-27 09:45:00; layover at STL: 70 minutes.
  • WN287: STL 2026-12-27 10:55:00 → MDW 2026-12-27 12:05:00.

2026-12-26 · one way · Axel-exclusive $210.25

• Southwest Airlines WN1789 / WN287: MCO 2026-12-26 08:10:00 → MDW 2026-12-26 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN1789: MCO 2026-12-26 08:10:00 → STL 2026-12-26 09:45:00; layover at STL: 70 minutes.
  • WN287: STL 2026-12-26 10:55:00 → MDW 2026-12-26 12:05:00.

2026-12-25 · one way · Axel-exclusive $210.25

• Southwest Airlines WN2777 / WN2106: MCO 2026-12-25 10:40:00 → MDW 2026-12-25 15:00:00; 1 stop(s) via RSW; 320 minutes. Local airport times.
  • WN2777: MCO 2026-12-25 10:40:00 → RSW 2026-12-25 11:45:00; layover at RSW: 80 minutes.
  • WN2106: RSW 2026-12-25 13:05:00 → MDW 2026-12-25 15:00:00.

2026-12-26 · one way · Axel-exclusive $210.25

• Southwest Airlines WN2777 / WN2106: MCO 2026-12-26 10:40:00 → MDW 2026-12-26 15:00:00; 1 stop(s) via RSW; 320 minutes. Local airport times.
  • WN2777: MCO 2026-12-26 10:40:00 → RSW 2026-12-26 11:45:00; layover at RSW: 80 minutes.
  • WN2106: RSW 2026-12-26 13:05:00 → MDW 2026-12-26 15:00:00.

2026-12-25 · one way · Axel-exclusive $210.25

• Southwest Airlines WN1915 / WN282: MCO 2026-12-25 15:40:00 → MDW 2026-12-25 19:50:00; 1 stop(s) via SDF; 310 minutes. Local airport times.
  • WN1915: MCO 2026-12-25 15:40:00 → SDF 2026-12-25 18:00:00; layover at SDF: 95 minutes.
  • WN282: SDF 2026-12-25 19:35:00 → MDW 2026-12-25 19:50:00.

2026-12-26 · one way · Axel-exclusive $210.25

• Southwest Airlines WN2840 / WN3556: MCO 2026-12-26 16:00:00 → MDW 2026-12-26 20:10:00; 1 stop(s) via PIT; 310 minutes. Local airport times.
  • WN2840: MCO 2026-12-26 16:00:00 → PIT 2026-12-26 18:25:00; layover at PIT: 75 minutes.
  • WN3556: PIT 2026-12-26 19:40:00 → MDW 2026-12-26 20:10:00.

2026-12-26 · one way · Axel-exclusive $210.25

• Southwest Airlines WN1915 / WN282: MCO 2026-12-26 15:40:00 → MDW 2026-12-26 19:50:00; 1 stop(s) via SDF; 310 minutes. Local airport times.
  • WN1915: MCO 2026-12-26 15:40:00 → SDF 2026-12-26 18:00:00; layover at SDF: 95 minutes.
  • WN282: SDF 2026-12-26 19:35:00 → MDW 2026-12-26 19:50:00.

2026-12-25 · one way · Axel-exclusive $210.25

• Southwest Airlines WN2840 / WN3556: MCO 2026-12-25 16:00:00 → MDW 2026-12-25 20:10:00; 1 stop(s) via PIT; 310 minutes. Local airport times.
  • WN2840: MCO 2026-12-25 16:00:00 → PIT 2026-12-25 18:25:00; layover at PIT: 75 minutes.
  • WN3556: PIT 2026-12-25 19:40:00 → MDW 2026-12-25 20:10:00.

2026-12-27 · one way · Axel-exclusive $210.25

• Southwest Airlines WN2840 / WN3556: MCO 2026-12-27 16:00:00 → MDW 2026-12-27 20:10:00; 1 stop(s) via PIT; 310 minutes. Local airport times.
  • WN2840: MCO 2026-12-27 16:00:00 → PIT 2026-12-27 18:25:00; layover at PIT: 75 minutes.
  • WN3556: PIT 2026-12-27 19:40:00 → MDW 2026-12-27 20:10:00.

2026-12-25 · one way · Axel-exclusive $210.25

• Southwest Airlines WN1789 / WN287: MCO 2026-12-25 08:10:00 → MDW 2026-12-25 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN1789: MCO 2026-12-25 08:10:00 → STL 2026-12-25 09:45:00; layover at STL: 70 minutes.
  • WN287: STL 2026-12-25 10:55:00 → MDW 2026-12-25 12:05:00.

2026-12-27 · one way · Axel-exclusive $253.75

• Delta Air Lines DL1150 / DL1076: MCO 2026-12-27 17:45:00 → MDW 2026-12-27 22:17:00; 1 stop(s) via ATL; 332 minutes. Local airport times.
  • DL1150: MCO 2026-12-27 17:45:00 → ATL 2026-12-27 19:25:00; layover at ATL: 115 minutes.
  • DL1076: ATL 2026-12-27 21:20:00 → MDW 2026-12-27 22:17:00.

2026-12-25 · one way · Axel-exclusive $253.75

• Delta Air Lines DL1150 / DL1076: MCO 2026-12-25 17:45:00 → MDW 2026-12-25 22:17:00; 1 stop(s) via ATL; 332 minutes. Local airport times.
  • DL1150: MCO 2026-12-25 17:45:00 → ATL 2026-12-25 19:25:00; layover at ATL: 115 minutes.
  • DL1076: ATL 2026-12-25 21:20:00 → MDW 2026-12-25 22:17:00.

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.

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