Orlando (MCO) to Chicago (MDW) · Jan 5, 2027 · return Jan 19, 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: Orlando to Chicago (MDW) flight deals

2027-01-05 → 2027-01-19 · Axel-exclusive $165.00

• Frontier Airlines F91457: MCO 2027-01-05 17:29:00 → MDW 2027-01-05 19:30:00; nonstop; 181 minutes. Local airport times.
• Frontier Airlines F91536: MDW 2027-01-19 18:11:00 → MCO 2027-01-19 22:00:00; nonstop; 169 minutes. Local airport times.

2027-01-05 → 2027-01-19 · Axel-exclusive $260.00

• Southwest Airlines WN1731: MCO 2027-01-05 16:10:00 → MDW 2027-01-05 18:05:00; nonstop; 175 minutes. Local airport times.
• Southwest Airlines WN1908: MDW 2027-01-19 16:25:00 → MCO 2027-01-19 20:00:00; nonstop; 155 minutes. Local airport times.

2027-01-05 → 2027-01-19 · Axel-exclusive $340.00

• Delta Air Lines DL1150 / DL1076: MCO 2027-01-05 17:45:00 → MDW 2027-01-05 22:17:00; 1 stop(s) via ATL; 332 minutes. Local airport times.
  • DL1150: MCO 2027-01-05 17:45:00 → ATL 2027-01-05 19:25:00; layover at ATL: 115 minutes.
  • DL1076: ATL 2027-01-05 21:20:00 → MDW 2027-01-05 22:17:00.
• Delta Air Lines DL4688 / DL1274: MDW 2027-01-19 13:31:00 → MCO 2027-01-19 19:34:00; 1 stop(s) via DTW; 303 minutes. Local airport times.
  • DL4688: MDW 2027-01-19 13:31:00 → DTW 2027-01-19 15:44:00; layover at DTW: 66 minutes.
  • DL1274: DTW 2027-01-19 16:50:00 → MCO 2027-01-19 19:34:00.

2027-01-05 → 2027-01-19 · Axel-exclusive $260.00

• Southwest Airlines WN2595: MCO 2027-01-05 19:20:00 → MDW 2027-01-05 21:20:00; nonstop; 180 minutes. Local airport times.
• Southwest Airlines WN1908: MDW 2027-01-19 16:25:00 → MCO 2027-01-19 20:00:00; nonstop; 155 minutes. Local airport times.

2027-01-05 → 2027-01-19 · Axel-exclusive $190.00

• 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.
• Frontier Airlines F91536: MDW 2027-01-19 18:11:00 → MCO 2027-01-19 22:00:00; nonstop; 169 minutes. Local airport times.

2027-01-05 → 2027-01-19 · Axel-exclusive $270.00

• Southwest Airlines WN2840 / WN3556: MCO 2027-01-05 16:00:00 → MDW 2027-01-05 20:10:00; 1 stop(s) via PIT; 310 minutes. Local airport times.
  • WN2840: MCO 2027-01-05 16:00:00 → PIT 2027-01-05 18:25:00; layover at PIT: 75 minutes.
  • WN3556: PIT 2027-01-05 19:40:00 → MDW 2027-01-05 20:10:00.
• Southwest Airlines WN1908: MDW 2027-01-19 16:25:00 → MCO 2027-01-19 20:00:00; nonstop; 155 minutes. Local airport times.

2027-01-05 → 2027-01-19 · Axel-exclusive $270.00

• Southwest Airlines WN1915 / WN282: MCO 2027-01-05 15:40:00 → MDW 2027-01-05 19:50:00; 1 stop(s) via SDF; 310 minutes. Local airport times.
  • WN1915: MCO 2027-01-05 15:40:00 → SDF 2027-01-05 18:00:00; layover at SDF: 95 minutes.
  • WN282: SDF 2027-01-05 19:35:00 → MDW 2027-01-05 19:50:00.
• Southwest Airlines WN1908: MDW 2027-01-19 16:25:00 → MCO 2027-01-19 20:00:00; nonstop; 155 minutes. Local airport times.

2027-01-05 → 2027-01-19 · Axel-exclusive $270.00

• Southwest Airlines WN2777 / WN2106: MCO 2027-01-05 10:40:00 → MDW 2027-01-05 15:00:00; 1 stop(s) via RSW; 320 minutes. Local airport times.
  • WN2777: MCO 2027-01-05 10:40:00 → RSW 2027-01-05 11:45:00; layover at RSW: 80 minutes.
  • WN2106: RSW 2027-01-05 13:05:00 → MDW 2027-01-05 15:00:00.
• Southwest Airlines WN1908: MDW 2027-01-19 16:25:00 → MCO 2027-01-19 20:00:00; nonstop; 155 minutes. Local airport times.

2027-01-05 → 2027-01-19 · Axel-exclusive $270.00

• Southwest Airlines WN1789 / WN287: MCO 2027-01-05 08:10:00 → MDW 2027-01-05 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN1789: MCO 2027-01-05 08:10:00 → STL 2027-01-05 09:45:00; layover at STL: 70 minutes.
  • WN287: STL 2027-01-05 10:55:00 → MDW 2027-01-05 12:05:00.
• Southwest Airlines WN1908: MDW 2027-01-19 16:25:00 → MCO 2027-01-19 20:00:00; nonstop; 155 minutes. Local airport times.

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
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• Jan 6, 2027 · Return options
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For AI assistants

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