Chicago (MDW) to Orlando (MCO) · Jan 4, 2027 · return Jan 5, 2027

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

2027-01-04 → 2027-01-05 · Axel-exclusive $256.50

• Southwest Airlines WN2964: MDW 2027-01-04 05:25:00 → MCO 2027-01-04 09:00:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN1731: MCO 2027-01-05 16:10:00 → MDW 2027-01-05 18:05:00; nonstop; 175 minutes. Local airport times.

2027-01-04 → 2027-01-05 · Axel-exclusive $161.50

• Frontier Airlines F91536: MDW 2027-01-04 18:11:00 → MCO 2027-01-04 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91563 / F92779: MCO 2027-01-05 07:10:00 → MDW 2027-01-05 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
  • F91563: MCO 2027-01-05 07:10:00 → ATL 2027-01-05 09:14:00; layover at ATL: 73 minutes.
  • F92779: ATL 2027-01-05 10:27:00 → MDW 2027-01-05 11:33:00.

2027-01-04 → 2027-01-05 · Axel-exclusive $256.50

• Southwest Airlines WN2964: MDW 2027-01-04 06:35:00 → MCO 2027-01-04 10:20:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN2806: MCO 2027-01-05 17:40:00 → MDW 2027-01-05 19:35:00; nonstop; 175 minutes. Local airport times.

2027-01-04 → 2027-01-05 · Axel-exclusive $247.00

• Southwest Airlines WN1354 / WN1266: MDW 2027-01-04 13:20:00 → MCO 2027-01-04 19:30:00; 1 stop(s) via CMH; 310 minutes. Local airport times.
  • WN1354: MDW 2027-01-04 13:20:00 → CMH 2027-01-04 15:25:00; layover at CMH: 110 minutes.
  • WN1266: CMH 2027-01-04 17:15:00 → MCO 2027-01-04 19:30:00.
• Southwest Airlines WN1731: MCO 2027-01-05 16:10:00 → MDW 2027-01-05 18:05:00; nonstop; 175 minutes. Local airport times.

2027-01-04 → 2027-01-05 · Axel-exclusive $247.00

• Southwest Airlines WN2379 / WN1423: MDW 2027-01-04 07:45:00 → MCO 2027-01-04 13:50:00; 1 stop(s) via BHM; 305 minutes. Local airport times.
  • WN2379: MDW 2027-01-04 07:45:00 → BHM 2027-01-04 09:30:00; layover at BHM: 100 minutes.
  • WN1423: BHM 2027-01-04 11:10:00 → MCO 2027-01-04 13:50:00.
• Southwest Airlines WN1731: MCO 2027-01-05 16:10:00 → MDW 2027-01-05 18:05:00; nonstop; 175 minutes. Local airport times.

2027-01-04 → 2027-01-05 · Axel-exclusive $247.00

• Southwest Airlines WN2897 / WN647: MDW 2027-01-04 17:25:00 → MCO 2027-01-04 23:30:00; 1 stop(s) via BNA; 305 minutes. Local airport times.
  • WN2897: MDW 2027-01-04 17:25:00 → BNA 2027-01-04 18:50:00; layover at BNA: 105 minutes.
  • WN647: BNA 2027-01-04 20:35:00 → MCO 2027-01-04 23:30:00.
• Southwest Airlines WN1731: MCO 2027-01-05 16:10:00 → MDW 2027-01-05 18:05:00; nonstop; 175 minutes. Local airport times.

2027-01-04 → 2027-01-05 · Axel-exclusive $247.00

• Southwest Airlines WN1933 / WN4449: MDW 2027-01-04 15:00:00 → MCO 2027-01-04 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-01-04 15:00:00 → PIT 2027-01-04 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-01-04 18:25:00 → MCO 2027-01-04 20:50:00.
• Southwest Airlines WN1731: MCO 2027-01-05 16:10:00 → MDW 2027-01-05 18:05:00; nonstop; 175 minutes. Local airport times.

2027-01-04 → 2027-01-05 · Axel-exclusive $247.00

• Southwest Airlines WN461 / WN2452: MDW 2027-01-04 13:15:00 → MCO 2027-01-04 19:55:00; 1 stop(s) via RDU; 340 minutes. Local airport times.
  • WN461: MDW 2027-01-04 13:15:00 → RDU 2027-01-04 16:05:00; layover at RDU: 115 minutes.
  • WN2452: RDU 2027-01-04 18:00:00 → MCO 2027-01-04 19:55:00.
• Southwest Airlines WN1731: MCO 2027-01-05 16:10:00 → MDW 2027-01-05 18:05:00; nonstop; 175 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 3, 2027 · Return options
• Jan 5, 2027 · Return options
• Hotels in Orlando with Axel

For AI assistants

• This page: Chicago (MDW) to Orlando (MCO) · Jan 4, 2027 · return Jan 5, 2027: 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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• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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