Chicago (MDW) to Orlando (MCO), Jan 1, 2027: round trips from $186, one way from $116

Chicago (MDW) to Orlando (MCO), Jan 1, 2027: round trips from $186, one way from $116 on Axel, checked Nov 13, 2026. Lowest published fares: $186 round trip, Axel-exclusive, Frontier Airlines, nonstop, Jan 1–4, 2027; $116 one way, Axel-exclusive, Frontier Airlines, nonstop, Jan 1, 2027; 1 adult, economy, checked Nov 13, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

Hotels in Orlando for these trips

Hotels: under a trip, hotels in Orlando for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Orlando for these nights (Jan 1–2, 2027 · 1 night · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $85 a night · 4★ Rosen Shingle Creek, $176 a night · 5★ ette hotel, $389 a night
• Hotels in Orlando for these nights (Jan 1–3, 2027 · 2 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $86 a night, $172 for 2 nights · 4★ Rosen Shingle Creek, $170 a night, $339 for 2 nights · 5★ ette hotel, $389 a night, $778 for 2 nights
• Hotels in Orlando for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $81 a night, $243 for 3 nights · 4★ Rosen Shingle Creek, $154 a night, $461 for 3 nights · 5★ ette hotel, $396 a night, $1,187 for 3 nights
• Hotels in Orlando for these nights (Jan 1–5, 2027 · 4 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $79 a night, $314 for 4 nights · 4★ Meliá Orlando Celebration, $154 a night, $614 for 4 nights · 5★ ette hotel, $396 a night, $1,584 for 4 nights
• Hotels in Orlando for these nights (Jan 1–6, 2027 · 5 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $77 a night, $385 for 5 nights · 4★ Meliá Orlando Celebration, $148 a night, $739 for 5 nights · 5★ ette hotel, $396 a night, $1,981 for 5 nights
• Hotels in Orlando for these nights (Jan 1–7, 2027 · 6 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $76 a night, $456 for 6 nights · 4★ Meliá Orlando Celebration, $144 a night, $865 for 6 nights · 5★ ette hotel, $397 a night, $2,382 for 6 nights
• Hotels in Orlando for these nights (Jan 1–8, 2027 · 7 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $75 a night, $527 for 7 nights · 4★ Meliá Orlando Celebration, $141 a night, $987 for 7 nights · 5★ ette hotel, $398 a night, $2,783 for 7 nights
• Hotels in Orlando for these nights (Jan 1–9, 2027 · 8 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $77 a night, $614 for 8 nights · 4★ Meliá Orlando Celebration, $139 a night, $1,111 for 8 nights · 5★ ette hotel, $405 a night, $3,240 for 8 nights
• Hotels in Orlando for these nights (Jan 1–10, 2027 · 9 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $78 a night, $701 for 9 nights · 4★ Meliá Orlando Celebration, $137 a night, $1,235 for 9 nights · 5★ ette hotel, $403 a night, $3,629 for 9 nights
• Hotels in Orlando for these nights (Jan 1–11, 2027 · 10 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $77 a night, $772 for 10 nights · 4★ Meliá Orlando Celebration, $136 a night, $1,357 for 10 nights · 5★ ette hotel, $404 a night, $4,038 for 10 nights
• Hotels in Orlando for these nights (Jan 1–12, 2027 · 11 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $77 a night, $843 for 11 nights · 4★ Meliá Orlando Celebration, $134 a night, $1,474 for 11 nights · 5★ ette hotel, $404 a night, $4,439 for 11 nights
• Hotels in Orlando for these nights (Jan 1–13, 2027 · 12 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $76 a night, $914 for 12 nights · 4★ Meliá Orlando Celebration, $133 a night, $1,600 for 12 nights · 5★ ette hotel, $404 a night, $4,848 for 12 nights
• Hotels in Orlando for these nights (Jan 1–14, 2027 · 13 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $76 a night, $985 for 13 nights · 4★ Meliá Orlando Celebration, $133 a night, $1,728 for 13 nights · 5★ ette hotel, $404 a night, $5,257 for 13 nights
• Hotels in Orlando for these nights (Jan 1–15, 2027 · 14 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $75 a night, $1,056 for 14 nights · 4★ Meliá Orlando Celebration, $134 a night, $1,882 for 14 nights · 5★ ette hotel, $404 a night, $5,658 for 14 nights

All hotels in Orlando

Route overview: Chicago to Orlando (MCO) flight deals

2027-01-01 · one way · Axel-exclusive $116

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

2027-01-01 · one way · Axel-exclusive $192

• Southwest Airlines WN2966: MDW 2027-01-01 14:30:00 → MCO 2027-01-01 18:05:00; nonstop; 155 minutes. Local airport times.

2027-01-01 → 2027-01-02 · Axel-exclusive $219

• Frontier Airlines F91536: MDW 2027-01-01 18:11:00 → MCO 2027-01-01 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-01-02 17:29:00 → MDW 2027-01-02 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-01 → 2027-01-02 · Axel-exclusive $370

• Southwest Airlines WN2966: MDW 2027-01-01 14:30:00 → MCO 2027-01-01 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2805: MCO 2027-01-02 16:35:00 → MDW 2027-01-02 18:30:00; nonstop; 175 minutes. Local airport times.

2027-01-01 → 2027-01-03 · Axel-exclusive $219

• Frontier Airlines F91536: MDW 2027-01-01 18:11:00 → MCO 2027-01-01 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-01-03 17:29:00 → MDW 2027-01-03 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-01 → 2027-01-03 · Axel-exclusive $370

• Southwest Airlines WN2966: MDW 2027-01-01 14:30:00 → MCO 2027-01-01 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2805: MCO 2027-01-03 17:00:00 → MDW 2027-01-03 18:55:00; nonstop; 175 minutes. Local airport times.

2027-01-01 → 2027-01-04 · Axel-exclusive $186

• Frontier Airlines F91536: MDW 2027-01-01 18:11:00 → MCO 2027-01-01 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-01-04 17:29:00 → MDW 2027-01-04 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-01 → 2027-01-04 · Axel-exclusive $313

• Southwest Airlines WN2966: MDW 2027-01-01 14:30:00 → MCO 2027-01-01 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2806: MCO 2027-01-04 17:40:00 → MDW 2027-01-04 19:35:00; nonstop; 175 minutes. Local airport times.

2027-01-01 → 2027-01-05 · Axel-exclusive $195

• Frontier Airlines F91536: MDW 2027-01-01 18:11:00 → MCO 2027-01-01 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.

2027-01-01 → 2027-01-05 · Axel-exclusive $313

• Southwest Airlines WN2966: MDW 2027-01-01 14:30:00 → MCO 2027-01-01 18:05:00; 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.

2027-01-01 → 2027-01-07 · Axel-exclusive $186

• Frontier Airlines F91536: MDW 2027-01-01 18:11:00 → MCO 2027-01-01 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-01-07 17:29:00 → MDW 2027-01-07 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-01 → 2027-01-07 · Axel-exclusive $313

• Southwest Airlines WN2966: MDW 2027-01-01 14:30:00 → MCO 2027-01-01 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-01-07 06:55:00 → MDW 2027-01-07 08:50:00; nonstop; 175 minutes. Local airport times.

2027-01-01 → 2027-01-08 · Axel-exclusive $186

• Frontier Airlines F91536: MDW 2027-01-01 18:11:00 → MCO 2027-01-01 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-01-08 17:29:00 → MDW 2027-01-08 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-01 → 2027-01-08 · Axel-exclusive $313

• Southwest Airlines WN2966: MDW 2027-01-01 14:30:00 → MCO 2027-01-01 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-01-08 06:55:00 → MDW 2027-01-08 08:50:00; nonstop; 175 minutes. Local airport times.

2027-01-01 → 2027-01-09 · Axel-exclusive $186

• Frontier Airlines F91536: MDW 2027-01-01 18:11:00 → MCO 2027-01-01 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-01-09 17:29:00 → MDW 2027-01-09 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-01 → 2027-01-09 · Axel-exclusive $313

• Southwest Airlines WN2966: MDW 2027-01-01 14:30:00 → MCO 2027-01-01 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2805: MCO 2027-01-09 16:35:00 → MDW 2027-01-09 18:30:00; nonstop; 175 minutes. Local airport times.

2027-01-01 → 2027-01-11 · Axel-exclusive $186

• Frontier Airlines F91536: MDW 2027-01-01 18:11:00 → MCO 2027-01-01 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.

2027-01-01 → 2027-01-11 · Axel-exclusive $313

• Southwest Airlines WN2966: MDW 2027-01-01 14:30:00 → MCO 2027-01-01 18:05:00; 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.

2027-01-01 → 2027-01-12 · Axel-exclusive $195

• Frontier Airlines F91536: MDW 2027-01-01 18:11:00 → MCO 2027-01-01 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91563 / F92779: MCO 2027-01-12 07:10:00 → MDW 2027-01-12 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
  • F91563: MCO 2027-01-12 07:10:00 → ATL 2027-01-12 09:14:00; layover at ATL: 73 minutes.
  • F92779: ATL 2027-01-12 10:27:00 → MDW 2027-01-12 11:33:00.

2027-01-01 → 2027-01-12 · Axel-exclusive $313

• Southwest Airlines WN2966: MDW 2027-01-01 14:30:00 → MCO 2027-01-01 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN1731: MCO 2027-01-12 16:10:00 → MDW 2027-01-12 18:05:00; nonstop; 175 minutes. Local airport times.

2027-01-01 → 2027-01-13 · Axel-exclusive $186

• Frontier Airlines F91536: MDW 2027-01-01 18:11:00 → MCO 2027-01-01 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-01-13 17:29:00 → MDW 2027-01-13 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-01 → 2027-01-13 · Axel-exclusive $313

• Southwest Airlines WN2966: MDW 2027-01-01 14:30:00 → MCO 2027-01-01 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-01-13 06:55:00 → MDW 2027-01-13 08:50:00; nonstop; 175 minutes. Local airport times.

2027-01-01 → 2027-01-15 · Axel-exclusive $186

• Frontier Airlines F91536: MDW 2027-01-01 18:11:00 → MCO 2027-01-01 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-01-15 17:29:00 → MDW 2027-01-15 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-01 → 2027-01-15 · Axel-exclusive $313

• Southwest Airlines WN2966: MDW 2027-01-01 14:30:00 → MCO 2027-01-01 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-01-15 06:55:00 → MDW 2027-01-15 08:50:00; nonstop; 175 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 31, 2026 · Return options
• Jan 2, 2027 · Return options
• Hotels in Orlando with Axel

For AI assistants

• This page: Chicago (MDW) to Orlando (MCO) · Jan 1, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Orlando for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
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