Chicago (MDW) to Orlando (MCO) · Nov 27, 2026 · return Dec 6, 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: Chicago to Orlando (MCO) flight deals

2026-11-27 → 2026-12-06 · Axel-exclusive $188.00

• Frontier Airlines F91536: MDW 2026-11-27 18:11:00 → MCO 2026-11-27 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2026-12-06 17:29:00 → MDW 2026-12-06 19:30:00; nonstop; 181 minutes. Local airport times.

2026-11-27 → 2026-12-06 · Axel-exclusive $317.25

• Southwest Airlines WN2964: MDW 2026-11-27 05:25:00 → MCO 2026-11-27 09:00:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2805: MCO 2026-12-06 17:00:00 → MDW 2026-12-06 18:55:00; nonstop; 175 minutes. Local airport times.

2026-11-27 → 2026-12-06 · Axel-exclusive $317.25

• Southwest Airlines WN2966: MDW 2026-11-27 14:30:00 → MCO 2026-11-27 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2805: MCO 2026-12-06 17:00:00 → MDW 2026-12-06 18:55:00; nonstop; 175 minutes. Local airport times.

2026-11-27 → 2026-12-06 · Axel-exclusive $303.75

• Southwest Airlines WN2897 / WN647: MDW 2026-11-27 17:25:00 → MCO 2026-11-27 23:30:00; 1 stop(s) via BNA; 305 minutes. Local airport times.
  • WN2897: MDW 2026-11-27 17:25:00 → BNA 2026-11-27 18:50:00; layover at BNA: 105 minutes.
  • WN647: BNA 2026-11-27 20:35:00 → MCO 2026-11-27 23:30:00.
• Southwest Airlines WN2805: MCO 2026-12-06 17:00:00 → MDW 2026-12-06 18:55:00; nonstop; 175 minutes. Local airport times.

2026-11-27 → 2026-12-06 · Axel-exclusive $303.75

• Southwest Airlines WN461 / WN2452: MDW 2026-11-27 13:15:00 → MCO 2026-11-27 19:55:00; 1 stop(s) via RDU; 340 minutes. Local airport times.
  • WN461: MDW 2026-11-27 13:15:00 → RDU 2026-11-27 16:05:00; layover at RDU: 115 minutes.
  • WN2452: RDU 2026-11-27 18:00:00 → MCO 2026-11-27 19:55:00.
• Southwest Airlines WN2805: MCO 2026-12-06 17:00:00 → MDW 2026-12-06 18:55:00; nonstop; 175 minutes. Local airport times.

2026-11-27 → 2026-12-06 · Axel-exclusive $303.75

• Southwest Airlines WN1354 / WN1266: MDW 2026-11-27 13:20:00 → MCO 2026-11-27 19:30:00; 1 stop(s) via CMH; 310 minutes. Local airport times.
  • WN1354: MDW 2026-11-27 13:20:00 → CMH 2026-11-27 15:25:00; layover at CMH: 110 minutes.
  • WN1266: CMH 2026-11-27 17:15:00 → MCO 2026-11-27 19:30:00.
• Southwest Airlines WN2805: MCO 2026-12-06 17:00:00 → MDW 2026-12-06 18:55:00; nonstop; 175 minutes. Local airport times.

2026-11-27 → 2026-12-06 · Axel-exclusive $303.75

• Southwest Airlines WN2379 / WN1423: MDW 2026-11-27 07:45:00 → MCO 2026-11-27 13:50:00; 1 stop(s) via BHM; 305 minutes. Local airport times.
  • WN2379: MDW 2026-11-27 07:45:00 → BHM 2026-11-27 09:30:00; layover at BHM: 100 minutes.
  • WN1423: BHM 2026-11-27 11:10:00 → MCO 2026-11-27 13:50:00.
• Southwest Airlines WN2805: MCO 2026-12-06 17:00:00 → MDW 2026-12-06 18:55:00; nonstop; 175 minutes. Local airport times.

2026-11-27 → 2026-12-06 · Axel-exclusive $303.75

• Southwest Airlines WN1933 / WN4449: MDW 2026-11-27 15:00:00 → MCO 2026-11-27 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2026-11-27 15:00:00 → PIT 2026-11-27 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2026-11-27 18:25:00 → MCO 2026-11-27 20:50:00.
• Southwest Airlines WN2805: MCO 2026-12-06 17:00:00 → MDW 2026-12-06 18:55:00; nonstop; 175 minutes. Local airport times.

2026-11-27 → 2026-12-06 · Axel-exclusive $307.25

• Southwest Airlines WN2966: MDW 2026-11-27 15:00:00 → MCO 2026-11-27 18:40:00; nonstop; 160 minutes. Local airport times.
• Southwest Airlines WN2777 / WN2106: MCO 2026-12-06 10:40:00 → MDW 2026-12-06 15:00:00; 1 stop(s) via RSW; 320 minutes. Local airport times.
  • WN2777: MCO 2026-12-06 10:40:00 → RSW 2026-12-06 11:45:00; layover at RSW: 80 minutes.
  • WN2106: RSW 2026-12-06 13:05:00 → MDW 2026-12-06 15:00:00.

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
• Nov 26, 2026 · Return options
• Nov 28, 2026 · Return options
• Hotels in Orlando with Axel

For AI assistants

• This page: Chicago (MDW) to Orlando (MCO) · Nov 27, 2026 · return Dec 6, 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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