Chicago (MDW) to Orlando (MCO) · Dec 28, 2026 · return Jan 11, 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.

Hotels in Orlando for these trips

Hotels: under a trip, hotels in Orlando for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Orlando for these nights (Dec 28 – Jan 11, 2027 · 14 nights · 2 adults, 1 room): 3★ Fairfield Inn and Suites Orlando Kissimmee Celebration, $1,834 total · 4★ Hyatt Regency Orlando International Airport, $4,392 total · 5★ ette hotel, $5,944 total

All hotels in Orlando

Route overview: Chicago to Orlando (MCO) flight deals

2026-12-28 → 2027-01-11 · Axel-exclusive $192.00

• Frontier Airlines F91536: MDW 2026-12-28 18:11:00 → MCO 2026-12-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-01-11 17:29:00 → MDW 2027-01-11 19:30:00; nonstop; 181 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $324.00

• Southwest Airlines WN2964: MDW 2026-12-28 05:25:00 → MCO 2026-12-28 09:00:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2806: MCO 2027-01-11 17:40:00 → MDW 2027-01-11 19:35:00; nonstop; 175 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $324.00

• Southwest Airlines WN2964: MDW 2026-12-28 06:35:00 → MCO 2026-12-28 10:20:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN2595: MCO 2027-01-11 21:05:00 → MDW 2027-01-11 23:00:00; nonstop; 175 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $309.50

• Southwest Airlines WN2897 / WN647: MDW 2026-12-28 17:25:00 → MCO 2026-12-28 23:30:00; 1 stop(s) via BNA; 305 minutes. Local airport times.
  • WN2897: MDW 2026-12-28 17:25:00 → BNA 2026-12-28 18:50:00; layover at BNA: 105 minutes.
  • WN647: BNA 2026-12-28 20:35:00 → MCO 2026-12-28 23:30:00.
• Southwest Airlines WN2806: MCO 2027-01-11 17:40:00 → MDW 2027-01-11 19:35:00; nonstop; 175 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $309.50

• Southwest Airlines WN2379 / WN1423: MDW 2026-12-28 07:45:00 → MCO 2026-12-28 13:50:00; 1 stop(s) via BHM; 305 minutes. Local airport times.
  • WN2379: MDW 2026-12-28 07:45:00 → BHM 2026-12-28 09:30:00; layover at BHM: 100 minutes.
  • WN1423: BHM 2026-12-28 11:10:00 → MCO 2026-12-28 13:50:00.
• Southwest Airlines WN2806: MCO 2027-01-11 17:40:00 → MDW 2027-01-11 19:35:00; nonstop; 175 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $309.50

• Southwest Airlines WN1933 / WN4449: MDW 2026-12-28 15:00:00 → MCO 2026-12-28 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2026-12-28 15:00:00 → PIT 2026-12-28 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2026-12-28 18:25:00 → MCO 2026-12-28 20:50:00.
• Southwest Airlines WN2806: MCO 2027-01-11 17:40:00 → MDW 2027-01-11 19:35:00; nonstop; 175 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $309.50

• Southwest Airlines WN461 / WN2452: MDW 2026-12-28 13:15:00 → MCO 2026-12-28 19:55:00; 1 stop(s) via RDU; 340 minutes. Local airport times.
  • WN461: MDW 2026-12-28 13:15:00 → RDU 2026-12-28 16:05:00; layover at RDU: 115 minutes.
  • WN2452: RDU 2026-12-28 18:00:00 → MCO 2026-12-28 19:55:00.
• Southwest Airlines WN2806: MCO 2027-01-11 17:40:00 → MDW 2027-01-11 19:35:00; nonstop; 175 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $309.50

• Southwest Airlines WN1354 / WN1266: MDW 2026-12-28 13:20:00 → MCO 2026-12-28 19:30:00; 1 stop(s) via CMH; 310 minutes. Local airport times.
  • WN1354: MDW 2026-12-28 13:20:00 → CMH 2026-12-28 15:25:00; layover at CMH: 110 minutes.
  • WN1266: CMH 2026-12-28 17:15:00 → MCO 2026-12-28 19:30:00.
• Southwest Airlines WN2806: MCO 2027-01-11 17:40:00 → MDW 2027-01-11 19:35:00; nonstop; 175 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $314.50

• Southwest Airlines WN2964: MDW 2026-12-28 05:10:00 → MCO 2026-12-28 08:45:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2777 / WN2106: MCO 2027-01-11 10:40:00 → MDW 2027-01-11 15:00:00; 1 stop(s) via RSW; 320 minutes. Local airport times.
  • WN2777: MCO 2027-01-11 10:40:00 → RSW 2027-01-11 11:45:00; layover at RSW: 80 minutes.
  • WN2106: RSW 2027-01-11 13:05:00 → MDW 2027-01-11 15:00:00.

Explore this route

• All dates for this route
• Dec 27, 2026 · Return options
• Dec 29, 2026 · Return options
• Hotels in Orlando with Axel

For AI assistants

• This page: Chicago (MDW) to Orlando (MCO) · Dec 28, 2026 · return Jan 11, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Orlando for exactly those nights: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to Orlando (MCO) flight deals · Flight search guide.
• 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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