Orlando (MCO) to Chicago (MDW) · Jan 4, 2027 · 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: Orlando to Chicago (MDW) flight deals

2027-01-04 · one way · Axel-exclusive $85.00

• Frontier Airlines F91457: MCO 2027-01-04 17:29:00 → MDW 2027-01-04 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-04 · one way · Axel-exclusive $135.00

• Southwest Airlines WN2595: MCO 2027-01-04 21:05:00 → MDW 2027-01-04 23:00:00; nonstop; 175 minutes. Local airport times.

2027-01-04 · one way · Axel-exclusive $175.00

• Delta Air Lines DL1150 / DL1076: MCO 2027-01-04 17:45:00 → MDW 2027-01-04 22:17:00; 1 stop(s) via ATL; 332 minutes. Local airport times.
  • DL1150: MCO 2027-01-04 17:45:00 → ATL 2027-01-04 19:25:00; layover at ATL: 115 minutes.
  • DL1076: ATL 2027-01-04 21:20:00 → MDW 2027-01-04 22:17:00.

2027-01-04 · one way · Axel-exclusive $135.00

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

2027-01-04 · one way · Axel-exclusive $110.00

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

2027-01-04 · one way · Axel-exclusive $145.00

• Southwest Airlines WN1789 / WN287: MCO 2027-01-04 08:10:00 → MDW 2027-01-04 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN1789: MCO 2027-01-04 08:10:00 → STL 2027-01-04 09:45:00; layover at STL: 70 minutes.
  • WN287: STL 2027-01-04 10:55:00 → MDW 2027-01-04 12:05:00.

2027-01-04 · one way · Axel-exclusive $145.00

• Southwest Airlines WN1915 / WN282: MCO 2027-01-04 15:40:00 → MDW 2027-01-04 19:50:00; 1 stop(s) via SDF; 310 minutes. Local airport times.
  • WN1915: MCO 2027-01-04 15:40:00 → SDF 2027-01-04 18:00:00; layover at SDF: 95 minutes.
  • WN282: SDF 2027-01-04 19:35:00 → MDW 2027-01-04 19:50:00.

2027-01-04 · one way · Axel-exclusive $145.00

• Southwest Airlines WN2840 / WN3556: MCO 2027-01-04 16:00:00 → MDW 2027-01-04 20:10:00; 1 stop(s) via PIT; 310 minutes. Local airport times.
  • WN2840: MCO 2027-01-04 16:00:00 → PIT 2027-01-04 18:25:00; layover at PIT: 75 minutes.
  • WN3556: PIT 2027-01-04 19:40:00 → MDW 2027-01-04 20:10:00.

2027-01-04 · one way · Axel-exclusive $145.00

• Southwest Airlines WN2777 / WN2106: MCO 2027-01-04 10:40:00 → MDW 2027-01-04 15:00:00; 1 stop(s) via RSW; 320 minutes. Local airport times.
  • WN2777: MCO 2027-01-04 10:40:00 → RSW 2027-01-04 11:45:00; layover at RSW: 80 minutes.
  • WN2106: RSW 2027-01-04 13:05:00 → MDW 2027-01-04 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
• Jan 3, 2027 · Return options
• Jan 5, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Orlando (MCO) to Chicago (MDW) · Jan 4, 2027 · one way: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
• 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.
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• 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 Orlando to Chicago (MDW) 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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