Chicago (MDW) to Orlando (MCO), May 28, 2027: round trips from $215, one way from $121

Chicago (MDW) to Orlando (MCO), May 28, 2027: round trips from $215, one way from $121 on Axel, checked Nov 14, 2026. Lowest published fares: $215 round trip, Axel-exclusive, Frontier Airlines, nonstop, May 28, 2027 – Jun 2, 2027; $121 one way, Axel-exclusive, Frontier Airlines, nonstop, May 28, 2027; 1 adult, economy, checked Nov 14, 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 (May 28–29, 2027 · 1 night · 2 adults, 1 room): 3★ Rosen Inn International, $75 a night · 4★ Meliá Orlando Celebration, $152 a night · 5★ ette hotel, $380 a night
• Hotels in Orlando for these nights (May 28–30, 2027 · 2 nights · 2 adults, 1 room): 3★ Rosen Inn International, $75 a night, $149 for 2 nights · 4★ Meliá Orlando Celebration, $150 a night, $300 for 2 nights · 5★ ette hotel, $378 a night, $756 for 2 nights
• Hotels in Orlando for these nights (May 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Rosen Inn International, $74 a night, $221 for 3 nights · 4★ Meliá Orlando Celebration, $143 a night, $429 for 3 nights · 5★ ette hotel, $380 a night, $1,140 for 3 nights
• Hotels in Orlando for these nights (May 28 – Jun 1, 2027 · 4 nights · 2 adults, 1 room): 3★ Rosen Inn International, $74 a night, $295 for 4 nights · 4★ Meliá Orlando Celebration, $140 a night, $558 for 4 nights · 5★ ette hotel, $351 a night, $1,404 for 4 nights
• Hotels in Orlando for these nights (May 28 – Jun 2, 2027 · 5 nights · 2 adults, 1 room): 3★ Rosen Inn International, $74 a night, $370 for 5 nights · 4★ Meliá Orlando Celebration, $141 a night, $706 for 5 nights · 5★ ette hotel, $343 a night, $1,716 for 5 nights
• Hotels in Orlando for these nights (May 28 – Jun 3, 2027 · 6 nights · 2 adults, 1 room): 3★ Rosen Inn International, $74 a night, $444 for 6 nights · 4★ Meliá Orlando Celebration, $142 a night, $854 for 6 nights · 5★ ette hotel, $338 a night, $2,028 for 6 nights
• Hotels in Orlando for these nights (May 28 – Jun 4, 2027 · 7 nights · 2 adults, 1 room): 3★ Rosen Inn International, $74 a night, $518 for 7 nights · 4★ Meliá Orlando Celebration, $143 a night, $1,002 for 7 nights · 5★ ette hotel, $327 a night, $2,292 for 7 nights
• Hotels in Orlando for these nights (May 28 – Jun 5, 2027 · 8 nights · 2 adults, 1 room): 3★ Rosen Inn International, $74 a night, $592 for 8 nights · 4★ Meliá Orlando Celebration, $144 a night, $1,148 for 8 nights · 5★ ette hotel, $321 a night, $2,570 for 8 nights
• Hotels in Orlando for these nights (May 28 – Jun 6, 2027 · 9 nights · 2 adults, 1 room): 3★ Rosen Inn International, $74 a night, $666 for 9 nights · 4★ Meliá Orlando Celebration, $144 a night, $1,298 for 9 nights · 5★ ette hotel, $320 a night, $2,877 for 9 nights
• Hotels in Orlando for these nights (May 28 – Jun 7, 2027 · 10 nights · 2 adults, 1 room): 3★ Rosen Inn International, $74 a night, $740 for 10 nights · 4★ Meliá Orlando Celebration, $143 a night, $1,425 for 10 nights · 5★ ette hotel, $314 a night, $3,141 for 10 nights
• Hotels in Orlando for these nights (May 28 – Jun 8, 2027 · 11 nights · 2 adults, 1 room): 3★ Rosen Inn International, $74 a night, $812 for 11 nights · 4★ Meliá Orlando Celebration, $142 a night, $1,561 for 11 nights · 5★ ette hotel, $309 a night, $3,395 for 11 nights
• Hotels in Orlando for these nights (May 28 – Jun 9, 2027 · 12 nights · 2 adults, 1 room): 3★ Rosen Inn International, $74 a night, $886 for 12 nights · 4★ Meliá Orlando Celebration, $141 a night, $1,697 for 12 nights · 5★ ette hotel, $305 a night, $3,659 for 12 nights
• Hotels in Orlando for these nights (May 28 – Jun 10, 2027 · 13 nights · 2 adults, 1 room): 3★ Rosen Inn International, $74 a night, $960 for 13 nights · 4★ Meliá Orlando Celebration, $141 a night, $1,833 for 13 nights · 5★ ette hotel, $303 a night, $3,945 for 13 nights
• Hotels in Orlando for these nights (May 28 – Jun 11, 2027 · 14 nights · 2 adults, 1 room): 3★ Rosen Inn International, $74 a night, $1,034 for 14 nights · 4★ Meliá Orlando Celebration, $141 a night, $1,969 for 14 nights · 5★ ette hotel, $300 a night, $4,199 for 14 nights

All hotels in Orlando

Route overview: Chicago to Orlando (MCO) flight deals

2027-05-28 · one way · Axel-exclusive $121

• Frontier Airlines F91536: MDW 2027-05-28 18:11:00 → MCO 2027-05-28 22:00:00; nonstop; 169 minutes. Local airport times.

2027-05-28 · one way · Axel-exclusive $184

• Southwest Airlines WN2966: MDW 2027-05-28 14:30:00 → MCO 2027-05-28 18:05:00; nonstop; 155 minutes. Local airport times.

2027-05-28 → 2027-05-29 · Axel-exclusive $230

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

2027-05-28 → 2027-05-29 · Axel-exclusive $357

• Southwest Airlines WN2966: MDW 2027-05-28 14:30:00 → MCO 2027-05-28 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2805: MCO 2027-05-29 16:35:00 → MDW 2027-05-29 18:30:00; nonstop; 175 minutes. Local airport times.

2027-05-28 → 2027-05-30 · Axel-exclusive $230

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

2027-05-28 → 2027-05-30 · Axel-exclusive $357

• Southwest Airlines WN2966: MDW 2027-05-28 14:30:00 → MCO 2027-05-28 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2805: MCO 2027-05-30 17:00:00 → MDW 2027-05-30 18:55:00; nonstop; 175 minutes. Local airport times.

2027-05-28 → 2027-05-31 · Axel-exclusive $230

• Frontier Airlines F91536: MDW 2027-05-28 18:11:00 → MCO 2027-05-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-05-31 17:29:00 → MDW 2027-05-31 19:30:00; nonstop; 181 minutes. Local airport times.

2027-05-28 → 2027-05-31 · Axel-exclusive $357

• Southwest Airlines WN2966: MDW 2027-05-28 14:30:00 → MCO 2027-05-28 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2806: MCO 2027-05-31 17:40:00 → MDW 2027-05-31 19:35:00; nonstop; 175 minutes. Local airport times.

2027-05-28 → 2027-06-01 · Axel-exclusive $225

• Frontier Airlines F91536: MDW 2027-05-28 18:11:00 → MCO 2027-05-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91563 / F92779: MCO 2027-06-01 07:10:00 → MDW 2027-06-01 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
  • F91563: MCO 2027-06-01 07:10:00 → ATL 2027-06-01 09:14:00; layover at ATL: 73 minutes.
  • F92779: ATL 2027-06-01 10:27:00 → MDW 2027-06-01 11:33:00.

2027-05-28 → 2027-06-01 · Axel-exclusive $333

• Southwest Airlines WN2966: MDW 2027-05-28 14:30:00 → MCO 2027-05-28 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN1731: MCO 2027-06-01 16:10:00 → MDW 2027-06-01 18:05:00; nonstop; 175 minutes. Local airport times.

2027-05-28 → 2027-06-03 · Axel-exclusive $215

• Frontier Airlines F91536: MDW 2027-05-28 18:11:00 → MCO 2027-05-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-06-03 17:29:00 → MDW 2027-06-03 19:30:00; nonstop; 181 minutes. Local airport times.

2027-05-28 → 2027-06-03 · Axel-exclusive $333

• Southwest Airlines WN2966: MDW 2027-05-28 14:30:00 → MCO 2027-05-28 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-06-03 06:55:00 → MDW 2027-06-03 08:50:00; nonstop; 175 minutes. Local airport times.

2027-05-28 → 2027-06-04 · Axel-exclusive $215

• Frontier Airlines F91536: MDW 2027-05-28 18:11:00 → MCO 2027-05-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-06-04 17:29:00 → MDW 2027-06-04 19:30:00; nonstop; 181 minutes. Local airport times.

2027-05-28 → 2027-06-04 · Axel-exclusive $333

• Southwest Airlines WN2966: MDW 2027-05-28 14:30:00 → MCO 2027-05-28 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-06-04 06:55:00 → MDW 2027-06-04 08:50:00; nonstop; 175 minutes. Local airport times.

2027-05-28 → 2027-06-05 · Axel-exclusive $215

• Frontier Airlines F91536: MDW 2027-05-28 18:11:00 → MCO 2027-05-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-06-05 17:29:00 → MDW 2027-06-05 19:30:00; nonstop; 181 minutes. Local airport times.

2027-05-28 → 2027-06-05 · Axel-exclusive $333

• Southwest Airlines WN2966: MDW 2027-05-28 14:30:00 → MCO 2027-05-28 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2805: MCO 2027-06-05 16:35:00 → MDW 2027-06-05 18:30:00; nonstop; 175 minutes. Local airport times.

2027-05-28 → 2027-06-07 · Axel-exclusive $215

• Frontier Airlines F91536: MDW 2027-05-28 18:11:00 → MCO 2027-05-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-06-07 17:29:00 → MDW 2027-06-07 19:30:00; nonstop; 181 minutes. Local airport times.

2027-05-28 → 2027-06-07 · Axel-exclusive $333

• Southwest Airlines WN2966: MDW 2027-05-28 14:30:00 → MCO 2027-05-28 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2806: MCO 2027-06-07 17:40:00 → MDW 2027-06-07 19:35:00; nonstop; 175 minutes. Local airport times.

2027-05-28 → 2027-06-08 · Axel-exclusive $225

• Frontier Airlines F91536: MDW 2027-05-28 18:11:00 → MCO 2027-05-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91563 / F92779: MCO 2027-06-08 07:10:00 → MDW 2027-06-08 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
  • F91563: MCO 2027-06-08 07:10:00 → ATL 2027-06-08 09:14:00; layover at ATL: 73 minutes.
  • F92779: ATL 2027-06-08 10:27:00 → MDW 2027-06-08 11:33:00.

2027-05-28 → 2027-06-08 · Axel-exclusive $333

• Southwest Airlines WN2966: MDW 2027-05-28 14:30:00 → MCO 2027-05-28 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN1731: MCO 2027-06-08 16:10:00 → MDW 2027-06-08 18:05:00; nonstop; 175 minutes. Local airport times.

2027-05-28 → 2027-06-09 · Axel-exclusive $215

• Frontier Airlines F91536: MDW 2027-05-28 18:11:00 → MCO 2027-05-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-06-09 17:29:00 → MDW 2027-06-09 19:30:00; nonstop; 181 minutes. Local airport times.

2027-05-28 → 2027-06-09 · Axel-exclusive $333

• Southwest Airlines WN2966: MDW 2027-05-28 14:30:00 → MCO 2027-05-28 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-06-09 06:55:00 → MDW 2027-06-09 08:50:00; nonstop; 175 minutes. Local airport times.

2027-05-28 → 2027-06-11 · Axel-exclusive $215

• Frontier Airlines F91536: MDW 2027-05-28 18:11:00 → MCO 2027-05-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-06-11 17:29:00 → MDW 2027-06-11 19:30:00; nonstop; 181 minutes. Local airport times.

2027-05-28 → 2027-06-11 · Axel-exclusive $333

• Southwest Airlines WN2966: MDW 2027-05-28 14:30:00 → MCO 2027-05-28 18:05:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-06-11 06:55:00 → MDW 2027-06-11 08:50:00; nonstop; 175 minutes. Local airport times.

Explore this route

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

For AI assistants

• This page: Chicago (MDW) to Orlando (MCO) · May 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.
• Next: each row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
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