Chicago (MDW) to Orlando (MCO), Feb 14, 2027: round trips from $176, one way from $102

Chicago (MDW) to Orlando (MCO), Feb 14, 2027: round trips from $176, one way from $102 on Axel, checked Nov 13, 2026. Lowest published fares: $176 round trip, Axel-exclusive, Frontier Airlines, nonstop, Feb 14–17, 2027; $102 one way, Axel-exclusive, Frontier Airlines, nonstop, Feb 14, 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 (Feb 14–15, 2027 · 1 night · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $70 a night · 4★ Meliá Orlando Celebration, $170 a night · 5★ ette hotel, $454 a night
• Hotels in Orlando for these nights (Feb 14–16, 2027 · 2 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $69 a night, $138 for 2 nights · 4★ Meliá Orlando Celebration, $170 a night, $340 for 2 nights · 5★ ette hotel, $432 a night, $863 for 2 nights
• Hotels in Orlando for these nights (Feb 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $69 a night, $208 for 3 nights · 4★ Meliá Orlando Celebration, $170 a night, $511 for 3 nights · 5★ ette hotel, $424 a night, $1,272 for 3 nights
• Hotels in Orlando for these nights (Feb 14–18, 2027 · 4 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $70 a night, $278 for 4 nights · 4★ Westgate Lakes Resort & Spa, $158 a night, $630 for 4 nights · 5★ ette hotel, $420 a night, $1,681 for 4 nights
• Hotels in Orlando for these nights (Feb 14–19, 2027 · 5 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $70 a night, $349 for 5 nights · 4★ Westgate Lakes Resort & Spa, $150 a night, $748 for 5 nights · 5★ ette hotel, $421 a night, $2,105 for 5 nights
• Hotels in Orlando for these nights (Feb 14–20, 2027 · 6 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $71 a night, $425 for 6 nights · 4★ Westgate Lakes Resort & Spa, $158 a night, $948 for 6 nights · 5★ ette hotel, $427 a night, $2,562 for 6 nights
• Hotels in Orlando for these nights (Feb 14–21, 2027 · 7 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $72 a night, $503 for 7 nights · 4★ Westgate Lakes Resort & Spa, $164 a night, $1,148 for 7 nights · 5★ ette hotel, $431 a night, $3,019 for 7 nights
• Hotels in Orlando for these nights (Feb 14–22, 2027 · 8 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $71 a night, $571 for 8 nights · 4★ Westgate Lakes Resort & Spa, $158 a night, $1,266 for 8 nights · 5★ ette hotel, $429 a night, $3,428 for 8 nights
• Hotels in Orlando for these nights (Feb 14–23, 2027 · 9 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $71 a night, $642 for 9 nights · 4★ Westgate Lakes Resort & Spa, $154 a night, $1,384 for 9 nights · 5★ ette hotel, $426 a night, $3,837 for 9 nights
• Hotels in Orlando for these nights (Feb 14–24, 2027 · 10 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $71 a night, $710 for 10 nights · 4★ Westgate Lakes Resort & Spa, $150 a night, $1,502 for 10 nights · 5★ ette hotel, $424 a night, $4,238 for 10 nights
• Hotels in Orlando for these nights (Feb 14–25, 2027 · 11 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $71 a night, $781 for 11 nights · 4★ Westgate Lakes Resort & Spa, $147 a night, $1,620 for 11 nights · 5★ ette hotel, $422 a night, $4,639 for 11 nights
• Hotels in Orlando for these nights (Feb 14–26, 2027 · 12 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $71 a night, $851 for 12 nights · 4★ Westgate Lakes Resort & Spa, $145 a night, $1,738 for 12 nights · 5★ ette hotel, $421 a night, $5,048 for 12 nights
• Hotels in Orlando for these nights (Feb 14–27, 2027 · 13 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $71 a night, $929 for 13 nights · 4★ Westgate Lakes Resort & Spa, $149 a night, $1,938 for 13 nights · 5★ ette hotel, $423 a night, $5,505 for 13 nights
• Hotels in Orlando for these nights (Feb 14–28, 2027 · 14 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $72 a night, $1,007 for 14 nights · 4★ Westgate Lakes Resort & Spa, $153 a night, $2,138 for 14 nights · 5★ ette hotel, $426 a night, $5,962 for 14 nights

All hotels in Orlando

Route overview: Chicago to Orlando (MCO) flight deals

2027-02-14 · one way · Axel-exclusive $102

• Frontier Airlines F91536: MDW 2027-02-14 18:11:00 → MCO 2027-02-14 22:00:00; nonstop; 169 minutes. Local airport times.

2027-02-14 · one way · Axel-exclusive $156

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-14 15:00:00 → MCO 2027-02-14 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-14 15:00:00 → PIT 2027-02-14 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-14 18:25:00 → MCO 2027-02-14 20:50:00.

2027-02-14 → 2027-02-15 · Axel-exclusive $192

• Frontier Airlines F91536: MDW 2027-02-14 18:11:00 → MCO 2027-02-14 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-15 17:29:00 → MDW 2027-02-15 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-14 → 2027-02-15 · Axel-exclusive $312

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-14 15:00:00 → MCO 2027-02-14 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-14 15:00:00 → PIT 2027-02-14 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-14 18:25:00 → MCO 2027-02-14 20:50:00.
• Southwest Airlines WN2806: MCO 2027-02-15 17:40:00 → MDW 2027-02-15 19:35:00; nonstop; 175 minutes. Local airport times.

2027-02-14 → 2027-02-16 · Axel-exclusive $204

• Frontier Airlines F91536: MDW 2027-02-14 18:11:00 → MCO 2027-02-14 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91563 / F92779: MCO 2027-02-16 07:10:00 → MDW 2027-02-16 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
  • F91563: MCO 2027-02-16 07:10:00 → ATL 2027-02-16 09:14:00; layover at ATL: 73 minutes.
  • F92779: ATL 2027-02-16 10:27:00 → MDW 2027-02-16 11:33:00.

2027-02-14 → 2027-02-16 · Axel-exclusive $312

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-14 15:00:00 → MCO 2027-02-14 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-14 15:00:00 → PIT 2027-02-14 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-14 18:25:00 → MCO 2027-02-14 20:50:00.
• Southwest Airlines WN1731: MCO 2027-02-16 16:10:00 → MDW 2027-02-16 18:05:00; nonstop; 175 minutes. Local airport times.

2027-02-14 → 2027-02-17 · Axel-exclusive $176

• Frontier Airlines F91536: MDW 2027-02-14 18:11:00 → MCO 2027-02-14 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-17 17:29:00 → MDW 2027-02-17 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-14 → 2027-02-17 · Axel-exclusive $285

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-14 15:00:00 → MCO 2027-02-14 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-14 15:00:00 → PIT 2027-02-14 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-14 18:25:00 → MCO 2027-02-14 20:50:00.
• Southwest Airlines WN2543: MCO 2027-02-17 06:55:00 → MDW 2027-02-17 08:50:00; nonstop; 175 minutes. Local airport times.

2027-02-14 → 2027-02-18 · Axel-exclusive $176

• Frontier Airlines F91536: MDW 2027-02-14 18:11:00 → MCO 2027-02-14 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-18 17:29:00 → MDW 2027-02-18 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-14 → 2027-02-18 · Axel-exclusive $285

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-14 15:00:00 → MCO 2027-02-14 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-14 15:00:00 → PIT 2027-02-14 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-14 18:25:00 → MCO 2027-02-14 20:50:00.
• Southwest Airlines WN2543: MCO 2027-02-18 06:55:00 → MDW 2027-02-18 08:50:00; nonstop; 175 minutes. Local airport times.

2027-02-14 → 2027-02-20 · Axel-exclusive $176

• Frontier Airlines F91536: MDW 2027-02-14 18:11:00 → MCO 2027-02-14 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-20 17:29:00 → MDW 2027-02-20 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-14 → 2027-02-20 · Axel-exclusive $285

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-14 15:00:00 → MCO 2027-02-14 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-14 15:00:00 → PIT 2027-02-14 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-14 18:25:00 → MCO 2027-02-14 20:50:00.
• Southwest Airlines WN2805: MCO 2027-02-20 16:35:00 → MDW 2027-02-20 18:30:00; nonstop; 175 minutes. Local airport times.

2027-02-14 → 2027-02-21 · Axel-exclusive $176

• Frontier Airlines F91536: MDW 2027-02-14 18:11:00 → MCO 2027-02-14 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-21 17:29:00 → MDW 2027-02-21 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-14 → 2027-02-21 · Axel-exclusive $285

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-14 15:00:00 → MCO 2027-02-14 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-14 15:00:00 → PIT 2027-02-14 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-14 18:25:00 → MCO 2027-02-14 20:50:00.
• Southwest Airlines WN2805: MCO 2027-02-21 17:00:00 → MDW 2027-02-21 18:55:00; nonstop; 175 minutes. Local airport times.

2027-02-14 → 2027-02-22 · Axel-exclusive $176

• Frontier Airlines F91536: MDW 2027-02-14 18:11:00 → MCO 2027-02-14 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-22 17:29:00 → MDW 2027-02-22 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-14 → 2027-02-22 · Axel-exclusive $285

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-14 15:00:00 → MCO 2027-02-14 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-14 15:00:00 → PIT 2027-02-14 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-14 18:25:00 → MCO 2027-02-14 20:50:00.
• Southwest Airlines WN2806: MCO 2027-02-22 17:40:00 → MDW 2027-02-22 19:35:00; nonstop; 175 minutes. Local airport times.

2027-02-14 → 2027-02-24 · Axel-exclusive $176

• Frontier Airlines F91536: MDW 2027-02-14 18:11:00 → MCO 2027-02-14 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-24 17:29:00 → MDW 2027-02-24 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-14 → 2027-02-24 · Axel-exclusive $285

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-14 15:00:00 → MCO 2027-02-14 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-14 15:00:00 → PIT 2027-02-14 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-14 18:25:00 → MCO 2027-02-14 20:50:00.
• Southwest Airlines WN2543: MCO 2027-02-24 06:55:00 → MDW 2027-02-24 08:50:00; nonstop; 175 minutes. Local airport times.

2027-02-14 → 2027-02-25 · Axel-exclusive $176

• Frontier Airlines F91536: MDW 2027-02-14 18:11:00 → MCO 2027-02-14 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-25 17:29:00 → MDW 2027-02-25 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-14 → 2027-02-25 · Axel-exclusive $285

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-14 15:00:00 → MCO 2027-02-14 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-14 15:00:00 → PIT 2027-02-14 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-14 18:25:00 → MCO 2027-02-14 20:50:00.
• Southwest Airlines WN2543: MCO 2027-02-25 06:55:00 → MDW 2027-02-25 08:50:00; nonstop; 175 minutes. Local airport times.

2027-02-14 → 2027-02-26 · Axel-exclusive $176

• Frontier Airlines F91536: MDW 2027-02-14 18:11:00 → MCO 2027-02-14 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-26 17:29:00 → MDW 2027-02-26 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-14 → 2027-02-26 · Axel-exclusive $285

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-14 15:00:00 → MCO 2027-02-14 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-14 15:00:00 → PIT 2027-02-14 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-14 18:25:00 → MCO 2027-02-14 20:50:00.
• Southwest Airlines WN2543: MCO 2027-02-26 06:55:00 → MDW 2027-02-26 08:50:00; nonstop; 175 minutes. Local airport times.

2027-02-14 → 2027-02-28 · Axel-exclusive $176

• Frontier Airlines F91536: MDW 2027-02-14 18:11:00 → MCO 2027-02-14 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-02-28 17:29:00 → MDW 2027-02-28 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-14 → 2027-02-28 · Axel-exclusive $285

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-14 15:00:00 → MCO 2027-02-14 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-14 15:00:00 → PIT 2027-02-14 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-14 18:25:00 → MCO 2027-02-14 20:50:00.
• Southwest Airlines WN2805: MCO 2027-02-28 17:00:00 → MDW 2027-02-28 18:55:00; nonstop; 175 minutes. Local airport times.

Explore this route

• All dates for this route
• Feb 13, 2027 · Return options
• Feb 15, 2027 · Return options
• Hotels in Orlando with Axel

For AI assistants

• This page: Chicago (MDW) to Orlando (MCO) · Feb 14, 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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• 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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