Orlando (MCO) to Chicago (MDW) · Nov 26, 2026 · return Dec 3, 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

2026-11-26 → 2026-12-03 · Axel-exclusive $193.88

• Frontier Airlines F91457: MCO 2026-11-26 17:29:00 → MDW 2026-11-26 19:30:00; nonstop; 181 minutes. Local airport times.
• Frontier Airlines F91536: MDW 2026-12-03 18:11:00 → MCO 2026-12-03 22:00:00; nonstop; 169 minutes. Local airport times.

2026-11-26 → 2026-12-03 · Axel-exclusive $305.50

• Southwest Airlines WN2595: MCO 2026-11-26 19:20:00 → MDW 2026-11-26 21:20:00; nonstop; 180 minutes. Local airport times.
• Southwest Airlines WN2964: MDW 2026-12-03 05:10:00 → MCO 2026-12-03 08:45:00; nonstop; 155 minutes. Local airport times.

2026-11-26 → 2026-12-03 · Axel-exclusive $399.50

• Delta Air Lines DL1150 / DL1076: MCO 2026-11-26 17:45:00 → MDW 2026-11-26 22:17:00; 1 stop(s) via ATL; 332 minutes. Local airport times.
  • DL1150: MCO 2026-11-26 17:45:00 → ATL 2026-11-26 19:25:00; layover at ATL: 115 minutes.
  • DL1076: ATL 2026-11-26 21:20:00 → MDW 2026-11-26 22:17:00.
• Delta Air Lines DL4688 / DL1274: MDW 2026-12-03 13:31:00 → MCO 2026-12-03 19:34:00; 1 stop(s) via DTW; 303 minutes. Local airport times.
  • DL4688: MDW 2026-12-03 13:31:00 → DTW 2026-12-03 15:44:00; layover at DTW: 66 minutes.
  • DL1274: DTW 2026-12-03 16:50:00 → MCO 2026-12-03 19:34:00.

2026-11-26 → 2026-12-03 · Axel-exclusive $305.50

• Southwest Airlines WN2806: MCO 2026-11-26 17:40:00 → MDW 2026-11-26 19:30:00; nonstop; 170 minutes. Local airport times.
• Southwest Airlines WN2964: MDW 2026-12-03 05:10:00 → MCO 2026-12-03 08:45:00; nonstop; 155 minutes. Local airport times.

2026-11-26 → 2026-12-03 · Axel-exclusive $227.63

• Frontier Airlines F91563 / F92779: MCO 2026-11-26 07:10:00 → MDW 2026-11-26 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
  • F91563: MCO 2026-11-26 07:10:00 → ATL 2026-11-26 09:14:00; layover at ATL: 73 minutes.
  • F92779: ATL 2026-11-26 10:27:00 → MDW 2026-11-26 11:33:00.
• Frontier Airlines F91536: MDW 2026-12-03 18:11:00 → MCO 2026-12-03 22:00:00; nonstop; 169 minutes. Local airport times.

2026-11-26 → 2026-12-03 · Axel-exclusive $319.00

• Southwest Airlines WN2777 / WN2106: MCO 2026-11-26 10:40:00 → MDW 2026-11-26 15:00:00; 1 stop(s) via RSW; 320 minutes. Local airport times.
  • WN2777: MCO 2026-11-26 10:40:00 → RSW 2026-11-26 11:45:00; layover at RSW: 80 minutes.
  • WN2106: RSW 2026-11-26 13:05:00 → MDW 2026-11-26 15:00:00.
• Southwest Airlines WN2964: MDW 2026-12-03 05:10:00 → MCO 2026-12-03 08:45:00; nonstop; 155 minutes. Local airport times.

2026-11-26 → 2026-12-03 · Axel-exclusive $319.00

• Southwest Airlines WN2840 / WN3556: MCO 2026-11-26 16:00:00 → MDW 2026-11-26 20:10:00; 1 stop(s) via PIT; 310 minutes. Local airport times.
  • WN2840: MCO 2026-11-26 16:00:00 → PIT 2026-11-26 18:25:00; layover at PIT: 75 minutes.
  • WN3556: PIT 2026-11-26 19:40:00 → MDW 2026-11-26 20:10:00.
• Southwest Airlines WN2964: MDW 2026-12-03 05:10:00 → MCO 2026-12-03 08:45:00; nonstop; 155 minutes. Local airport times.

2026-11-26 → 2026-12-03 · Axel-exclusive $319.00

• Southwest Airlines WN1789 / WN287: MCO 2026-11-26 08:10:00 → MDW 2026-11-26 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN1789: MCO 2026-11-26 08:10:00 → STL 2026-11-26 09:45:00; layover at STL: 70 minutes.
  • WN287: STL 2026-11-26 10:55:00 → MDW 2026-11-26 12:05:00.
• Southwest Airlines WN2964: MDW 2026-12-03 05:10:00 → MCO 2026-12-03 08:45:00; nonstop; 155 minutes. Local airport times.

2026-11-26 → 2026-12-03 · Axel-exclusive $319.00

• Southwest Airlines WN1915 / WN282: MCO 2026-11-26 15:40:00 → MDW 2026-11-26 19:50:00; 1 stop(s) via SDF; 310 minutes. Local airport times.
  • WN1915: MCO 2026-11-26 15:40:00 → SDF 2026-11-26 18:00:00; layover at SDF: 95 minutes.
  • WN282: SDF 2026-11-26 19:35:00 → MDW 2026-11-26 19:50:00.
• Southwest Airlines WN2964: MDW 2026-12-03 05:10:00 → MCO 2026-12-03 08:45:00; nonstop; 155 minutes. Local airport times.

Explore this route

• All dates for this route
• Nov 25, 2026 · Return options
• Nov 27, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Orlando (MCO) to Chicago (MDW) · Nov 26, 2026 · return Dec 3, 2026: 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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