Orlando (MCO) to Chicago (MDW) · Dec 16, 2026 · one way

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

2026-12-16 · one way · Axel-exclusive $85.00

• Frontier Airlines F91457: MCO 2026-12-16 17:29:00 → MDW 2026-12-16 19:30:00; nonstop; 181 minutes. Local airport times.

2026-12-16 · one way · Axel-exclusive $135.00

• Southwest Airlines WN2806: MCO 2026-12-16 17:40:00 → MDW 2026-12-16 19:35:00; nonstop; 175 minutes. Local airport times.

2026-12-16 · one way · Axel-exclusive $175.00

• Delta Air Lines DL1150 / DL1076: MCO 2026-12-16 17:45:00 → MDW 2026-12-16 22:17:00; 1 stop(s) via ATL; 332 minutes. Local airport times.
  • DL1150: MCO 2026-12-16 17:45:00 → ATL 2026-12-16 19:25:00; layover at ATL: 115 minutes.
  • DL1076: ATL 2026-12-16 21:20:00 → MDW 2026-12-16 22:17:00.

2026-12-16 · one way · Axel-exclusive $135.00

• Southwest Airlines WN2543: MCO 2026-12-16 06:55:00 → MDW 2026-12-16 08:50:00; nonstop; 175 minutes. Local airport times.

2026-12-16 · one way · Axel-exclusive $110.00

• Frontier Airlines F91563 / F92779: MCO 2026-12-16 07:10:00 → MDW 2026-12-16 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
  • F91563: MCO 2026-12-16 07:10:00 → ATL 2026-12-16 09:14:00; layover at ATL: 73 minutes.
  • F92779: ATL 2026-12-16 10:27:00 → MDW 2026-12-16 11:33:00.

2026-12-16 · one way · Axel-exclusive $145.00

• Southwest Airlines WN2777 / WN2106: MCO 2026-12-16 10:40:00 → MDW 2026-12-16 15:00:00; 1 stop(s) via RSW; 320 minutes. Local airport times.
  • WN2777: MCO 2026-12-16 10:40:00 → RSW 2026-12-16 11:45:00; layover at RSW: 80 minutes.
  • WN2106: RSW 2026-12-16 13:05:00 → MDW 2026-12-16 15:00:00.

2026-12-16 · one way · Axel-exclusive $145.00

• Southwest Airlines WN1915 / WN282: MCO 2026-12-16 15:40:00 → MDW 2026-12-16 19:50:00; 1 stop(s) via SDF; 310 minutes. Local airport times.
  • WN1915: MCO 2026-12-16 15:40:00 → SDF 2026-12-16 18:00:00; layover at SDF: 95 minutes.
  • WN282: SDF 2026-12-16 19:35:00 → MDW 2026-12-16 19:50:00.

2026-12-16 · one way · Axel-exclusive $145.00

• Southwest Airlines WN1789 / WN287: MCO 2026-12-16 08:10:00 → MDW 2026-12-16 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN1789: MCO 2026-12-16 08:10:00 → STL 2026-12-16 09:45:00; layover at STL: 70 minutes.
  • WN287: STL 2026-12-16 10:55:00 → MDW 2026-12-16 12:05:00.

2026-12-16 · one way · Axel-exclusive $145.00

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

Explore this route

• All dates for this route
• Dec 15, 2026 · Return options
• Dec 17, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Orlando (MCO) to Chicago (MDW) · Dec 16, 2026 · one way: 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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