Chicago (MDW) to Orlando (MCO), Jan 28, 2027: round trips from $152, one way from $81

Chicago (MDW) to Orlando (MCO), Jan 28, 2027: round trips from $152, one way from $81 on Axel, checked Nov 13, 2026. Lowest published fares: $152 round trip, Axel-exclusive, Frontier Airlines, nonstop, Jan 28–29, 2027; $81 one way, Axel-exclusive, Frontier Airlines, nonstop, Jan 28, 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 28–29, 2027 · 1 night · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $69 a night · 4★ Westgate Lakes Resort & Spa, $124 a night · 5★ ette hotel, $416 a night
• Hotels in Orlando for these nights (Jan 28–30, 2027 · 2 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $78 a night, $155 for 2 nights · 4★ Westgate Lakes Resort & Spa, $152 a night, $303 for 2 nights · 5★ ette hotel, $403 a night, $805 for 2 nights
• Hotels in Orlando for these nights (Jan 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $80 a night, $240 for 3 nights · 4★ Westgate Lakes Resort & Spa, $161 a night, $482 for 3 nights · 5★ ette hotel, $421 a night, $1,262 for 3 nights
• Hotels in Orlando for these nights (Jan 28 – Feb 1, 2027 · 4 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $77 a night, $309 for 4 nights · 4★ Westgate Lakes Resort & Spa, $150 a night, $601 for 4 nights · 5★ ette hotel, $420 a night, $1,678 for 4 nights
• Hotels in Orlando for these nights (Jan 28 – Feb 2, 2027 · 5 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $76 a night, $379 for 5 nights · 4★ Westgate Lakes Resort & Spa, $144 a night, $719 for 5 nights · 5★ ette hotel, $416 a night, $2,079 for 5 nights
• Hotels in Orlando for these nights (Jan 28 – Feb 3, 2027 · 6 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $75 a night, $449 for 6 nights · 4★ Westgate Lakes Resort & Spa, $140 a night, $837 for 6 nights · 5★ ette hotel, $405 a night, $2,427 for 6 nights
• Hotels in Orlando for these nights (Jan 28 – Feb 4, 2027 · 7 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $74 a night, $519 for 7 nights · 4★ Westgate Lakes Resort & Spa, $137 a night, $957 for 7 nights · 5★ ette hotel, $405 a night, $2,836 for 7 nights
• Hotels in Orlando for these nights (Jan 28 – Feb 5, 2027 · 8 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $74 a night, $589 for 8 nights · 4★ Westgate Lakes Resort & Spa, $134 a night, $1,075 for 8 nights · 5★ ette hotel, $405 a night, $3,237 for 8 nights
• Hotels in Orlando for these nights (Jan 28 – Feb 6, 2027 · 9 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $74 a night, $665 for 9 nights · 4★ Westgate Lakes Resort & Spa, $143 a night, $1,287 for 9 nights · 5★ ette hotel, $410 a night, $3,694 for 9 nights
• Hotels in Orlando for these nights (Jan 28 – Feb 7, 2027 · 10 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $74 a night, $743 for 10 nights · 4★ Westgate Lakes Resort & Spa, $150 a night, $1,499 for 10 nights · 5★ ette hotel, $414 a night, $4,142 for 10 nights
• Hotels in Orlando for these nights (Jan 28 – Feb 8, 2027 · 11 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $74 a night, $814 for 11 nights · 4★ Westgate Lakes Resort & Spa, $156 a night, $1,711 for 11 nights · 5★ ette hotel, $413 a night, $4,543 for 11 nights
• Hotels in Orlando for these nights (Jan 28 – Feb 9, 2027 · 12 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $74 a night, $884 for 12 nights · 4★ Westgate Lakes Resort & Spa, $160 a night, $1,923 for 12 nights · 5★ ette hotel, $413 a night, $4,952 for 12 nights
• Hotels in Orlando for these nights (Jan 28 – Feb 10, 2027 · 13 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $73 a night, $955 for 13 nights · 4★ Westgate Lakes Resort & Spa, $164 a night, $2,135 for 13 nights · 5★ ette hotel, $412 a night, $5,353 for 13 nights
• Hotels in Orlando for these nights (Jan 28 – Feb 11, 2027 · 14 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $73 a night, $1,025 for 14 nights · 4★ Meliá Orlando Celebration, $166 a night, $2,317 for 14 nights · 5★ ette hotel, $412 a night, $5,769 for 14 nights

All hotels in Orlando

Route overview: Chicago to Orlando (MCO) flight deals

2027-01-28 · one way · Axel-exclusive $81

• Frontier Airlines F91536: MDW 2027-01-28 18:11:00 → MCO 2027-01-28 22:00:00; nonstop; 169 minutes. Local airport times.

2027-01-28 · one way · Axel-exclusive $133

• Southwest Airlines WN2964: MDW 2027-01-28 05:10:00 → MCO 2027-01-28 08:45:00; nonstop; 155 minutes. Local airport times.

2027-01-28 → 2027-01-29 · Axel-exclusive $152

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

2027-01-28 → 2027-01-29 · Axel-exclusive $257

• Southwest Airlines WN2964: MDW 2027-01-28 05:10:00 → MCO 2027-01-28 08:45:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-01-29 06:55:00 → MDW 2027-01-29 08:50:00; nonstop; 175 minutes. Local airport times.

2027-01-28 → 2027-01-30 · Axel-exclusive $152

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

2027-01-28 → 2027-01-30 · Axel-exclusive $257

• Southwest Airlines WN2964: MDW 2027-01-28 05:10:00 → MCO 2027-01-28 08:45:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2805: MCO 2027-01-30 16:35:00 → MDW 2027-01-30 18:30:00; nonstop; 175 minutes. Local airport times.

2027-01-28 → 2027-01-31 · Axel-exclusive $152

• Frontier Airlines F91536: MDW 2027-01-28 18:11:00 → MCO 2027-01-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-01-31 17:29:00 → MDW 2027-01-31 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-28 → 2027-01-31 · Axel-exclusive $257

• Southwest Airlines WN2964: MDW 2027-01-28 05:10:00 → MCO 2027-01-28 08:45:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2805: MCO 2027-01-31 17:00:00 → MDW 2027-01-31 18:55:00; nonstop; 175 minutes. Local airport times.

2027-01-28 → 2027-02-01 · Axel-exclusive $156

• Frontier Airlines F91536: MDW 2027-01-28 18:11:00 → MCO 2027-01-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-01 17:29:00 → MDW 2027-02-01 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-28 → 2027-02-01 · Axel-exclusive $263

• Southwest Airlines WN2964: MDW 2027-01-28 05:10:00 → MCO 2027-01-28 08:45:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2806: MCO 2027-02-01 17:40:00 → MDW 2027-02-01 19:35:00; nonstop; 175 minutes. Local airport times.

2027-01-28 → 2027-02-03 · Axel-exclusive $156

• Frontier Airlines F91536: MDW 2027-01-28 18:11:00 → MCO 2027-01-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-03 17:29:00 → MDW 2027-02-03 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-28 → 2027-02-03 · Axel-exclusive $263

• Southwest Airlines WN2964: MDW 2027-01-28 05:10:00 → MCO 2027-01-28 08:45:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-02-03 06:55:00 → MDW 2027-02-03 08:50:00; nonstop; 175 minutes. Local airport times.

2027-01-28 → 2027-02-04 · Axel-exclusive $156

• Frontier Airlines F91536: MDW 2027-01-28 18:11:00 → MCO 2027-01-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-04 17:29:00 → MDW 2027-02-04 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-28 → 2027-02-04 · Axel-exclusive $263

• Southwest Airlines WN2964: MDW 2027-01-28 05:10:00 → MCO 2027-01-28 08:45:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-02-04 06:55:00 → MDW 2027-02-04 08:50:00; nonstop; 175 minutes. Local airport times.

2027-01-28 → 2027-02-05 · Axel-exclusive $156

• Frontier Airlines F91536: MDW 2027-01-28 18:11:00 → MCO 2027-01-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-05 17:29:00 → MDW 2027-02-05 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-28 → 2027-02-05 · Axel-exclusive $263

• Southwest Airlines WN2964: MDW 2027-01-28 05:10:00 → MCO 2027-01-28 08:45:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-02-05 06:55:00 → MDW 2027-02-05 08:50:00; nonstop; 175 minutes. Local airport times.

2027-01-28 → 2027-02-07 · Axel-exclusive $156

• Frontier Airlines F91536: MDW 2027-01-28 18:11:00 → MCO 2027-01-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-07 17:29:00 → MDW 2027-02-07 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-28 → 2027-02-07 · Axel-exclusive $263

• Southwest Airlines WN2964: MDW 2027-01-28 05:10:00 → MCO 2027-01-28 08:45:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2805: MCO 2027-02-07 17:00:00 → MDW 2027-02-07 18:55:00; nonstop; 175 minutes. Local airport times.

2027-01-28 → 2027-02-08 · Axel-exclusive $156

• Frontier Airlines F91536: MDW 2027-01-28 18:11:00 → MCO 2027-01-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-08 17:29:00 → MDW 2027-02-08 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-28 → 2027-02-08 · Axel-exclusive $263

• Southwest Airlines WN2964: MDW 2027-01-28 05:10:00 → MCO 2027-01-28 08:45:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2806: MCO 2027-02-08 17:40:00 → MDW 2027-02-08 19:35:00; nonstop; 175 minutes. Local airport times.

2027-01-28 → 2027-02-09 · Axel-exclusive $166

• Frontier Airlines F91536: MDW 2027-01-28 18:11:00 → MCO 2027-01-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91563 / F92779: MCO 2027-02-09 07:10:00 → MDW 2027-02-09 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
  • F91563: MCO 2027-02-09 07:10:00 → ATL 2027-02-09 09:14:00; layover at ATL: 73 minutes.
  • F92779: ATL 2027-02-09 10:27:00 → MDW 2027-02-09 11:33:00.

2027-01-28 → 2027-02-09 · Axel-exclusive $263

• Southwest Airlines WN2964: MDW 2027-01-28 05:10:00 → MCO 2027-01-28 08:45:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN1731: MCO 2027-02-09 16:10:00 → MDW 2027-02-09 18:05:00; nonstop; 175 minutes. Local airport times.

2027-01-28 → 2027-02-11 · Axel-exclusive $156

• Frontier Airlines F91536: MDW 2027-01-28 18:11:00 → MCO 2027-01-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-11 17:29:00 → MDW 2027-02-11 19:30:00; nonstop; 181 minutes. Local airport times.

2027-01-28 → 2027-02-11 · Axel-exclusive $263

• Southwest Airlines WN2964: MDW 2027-01-28 05:10:00 → MCO 2027-01-28 08:45:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-02-11 06:55:00 → MDW 2027-02-11 08:50:00; nonstop; 175 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 27, 2027 · Return options
• Jan 29, 2027 · Return options
• Hotels in Orlando with Axel

For AI assistants

• This page: Chicago (MDW) to Orlando (MCO) · Jan 28, 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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