Chicago (MDW) to Orlando (MCO) · Dec 31, 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: Chicago to Orlando (MCO) flight deals

2026-12-31 · one way · Axel-exclusive $123.25

• Frontier Airlines F91536: MDW 2026-12-31 18:11:00 → MCO 2026-12-31 22:00:00; nonstop; 169 minutes. Local airport times.

2026-12-31 · one way · Axel-exclusive $203.00

• Southwest Airlines WN2964: MDW 2026-12-31 05:10:00 → MCO 2026-12-31 08:45:00; nonstop; 155 minutes. Local airport times.

2026-12-31 · one way · Axel-exclusive $268.25

• Delta Air Lines DL4688 / DL1274: MDW 2026-12-31 13:31:00 → MCO 2026-12-31 19:34:00; 1 stop(s) via DTW; 303 minutes. Local airport times.
  • DL4688: MDW 2026-12-31 13:31:00 → DTW 2026-12-31 15:44:00; layover at DTW: 66 minutes.
  • DL1274: DTW 2026-12-31 16:50:00 → MCO 2026-12-31 19:34:00.

2026-12-31 · one way · Axel-exclusive $203.00

• Southwest Airlines WN4565: MDW 2026-12-31 07:50:00 → MCO 2026-12-31 11:35:00; nonstop; 165 minutes. Local airport times.

2026-12-31 · one way · Axel-exclusive $188.50

• Southwest Airlines WN1354 / WN1266: MDW 2026-12-31 13:20:00 → MCO 2026-12-31 19:30:00; 1 stop(s) via CMH; 310 minutes. Local airport times.
  • WN1354: MDW 2026-12-31 13:20:00 → CMH 2026-12-31 15:25:00; layover at CMH: 110 minutes.
  • WN1266: CMH 2026-12-31 17:15:00 → MCO 2026-12-31 19:30:00.

2026-12-31 · one way · Axel-exclusive $188.50

• Southwest Airlines WN2897 / WN647: MDW 2026-12-31 17:25:00 → MCO 2026-12-31 23:30:00; 1 stop(s) via BNA; 305 minutes. Local airport times.
  • WN2897: MDW 2026-12-31 17:25:00 → BNA 2026-12-31 18:50:00; layover at BNA: 105 minutes.
  • WN647: BNA 2026-12-31 20:35:00 → MCO 2026-12-31 23:30:00.

2026-12-31 · one way · Axel-exclusive $188.50

• Southwest Airlines WN461 / WN2452: MDW 2026-12-31 13:15:00 → MCO 2026-12-31 19:55:00; 1 stop(s) via RDU; 340 minutes. Local airport times.
  • WN461: MDW 2026-12-31 13:15:00 → RDU 2026-12-31 16:05:00; layover at RDU: 115 minutes.
  • WN2452: RDU 2026-12-31 18:00:00 → MCO 2026-12-31 19:55:00.

2026-12-31 · one way · Axel-exclusive $188.50

• Southwest Airlines WN2379 / WN1423: MDW 2026-12-31 07:45:00 → MCO 2026-12-31 13:50:00; 1 stop(s) via BHM; 305 minutes. Local airport times.
  • WN2379: MDW 2026-12-31 07:45:00 → BHM 2026-12-31 09:30:00; layover at BHM: 100 minutes.
  • WN1423: BHM 2026-12-31 11:10:00 → MCO 2026-12-31 13:50:00.

2026-12-31 · one way · Axel-exclusive $188.50

• Southwest Airlines WN1933 / WN4449: MDW 2026-12-31 15:00:00 → MCO 2026-12-31 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2026-12-31 15:00:00 → PIT 2026-12-31 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2026-12-31 18:25:00 → MCO 2026-12-31 20:50:00.

Explore this route

• All dates for this route
• Dec 30, 2026 · Return options
• Jan 1, 2027 · Return options
• Hotels in Orlando with Axel

For AI assistants

• This page: Chicago (MDW) to Orlando (MCO) · Dec 31, 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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