Chicago (MDW) to Orlando (MCO), Feb 28, 2027: round trips from $164, one way from $85

Chicago (MDW) to Orlando (MCO), Feb 28, 2027: round trips from $164, one way from $85 on Axel, checked Nov 13, 2026. Lowest published fares: $164 round trip, Axel-exclusive, Frontier Airlines, nonstop, Feb 28, 2027 – Mar 1, 2027; $85 one way, Axel-exclusive, Frontier Airlines, nonstop, Feb 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 (Feb 28 – Mar 1, 2027 · 1 night · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $71 a night · 4★ Meliá Orlando Celebration, $170 a night · 5★ ette hotel, $401 a night
• Hotels in Orlando for these nights (Feb 28 – Mar 2, 2027 · 2 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $77 a night, $153 for 2 nights · 4★ Meliá Orlando Celebration, $168 a night, $335 for 2 nights · 5★ ette hotel, $405 a night, $810 for 2 nights
• Hotels in Orlando for these nights (Feb 28 – Mar 3, 2027 · 3 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $78 a night, $234 for 3 nights · 4★ Meliá Orlando Celebration, $167 a night, $500 for 3 nights · 5★ ette hotel, $404 a night, $1,211 for 3 nights
• Hotels in Orlando for these nights (Feb 28 – Mar 4, 2027 · 4 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $79 a night, $315 for 4 nights · 4★ Meliá Orlando Celebration, $167 a night, $668 for 4 nights · 5★ ette hotel, $405 a night, $1,620 for 4 nights
• Hotels in Orlando for these nights (Feb 28 – Mar 5, 2027 · 5 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $79 a night, $397 for 5 nights · 4★ Meliá Orlando Celebration, $167 a night, $833 for 5 nights · 5★ ette hotel, $406 a night, $2,029 for 5 nights
• Hotels in Orlando for these nights (Feb 28 – Mar 6, 2027 · 6 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $82 a night, $493 for 6 nights · 4★ Meliá Orlando Celebration, $167 a night, $1,003 for 6 nights · 5★ ette hotel, $413 a night, $2,477 for 6 nights
• Hotels in Orlando for these nights (Feb 28 – Mar 7, 2027 · 7 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $85 a night, $595 for 7 nights · 4★ Meliá Orlando Celebration, $167 a night, $1,170 for 7 nights · 5★ ette hotel, $420 a night, $2,942 for 7 nights
• Hotels in Orlando for these nights (Feb 28 – Mar 8, 2027 · 8 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $85 a night, $676 for 8 nights · 4★ Meliá Orlando Celebration, $167 a night, $1,337 for 8 nights · 5★ ette hotel, $419 a night, $3,351 for 8 nights
• Hotels in Orlando for these nights (Feb 28 – Mar 9, 2027 · 9 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $84 a night, $758 for 9 nights · 4★ Meliá Orlando Celebration, $166 a night, $1,496 for 9 nights · 5★ ette hotel, $417 a night, $3,752 for 9 nights
• Hotels in Orlando for these nights (Feb 28 – Mar 10, 2027 · 10 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $84 a night, $837 for 10 nights · 4★ Meliá Orlando Celebration, $166 a night, $1,657 for 10 nights · 5★ ette hotel, $416 a night, $4,161 for 10 nights
• Hotels in Orlando for these nights (Feb 28 – Mar 11, 2027 · 11 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $84 a night, $919 for 11 nights · 4★ Meliá Orlando Celebration, $165 a night, $1,816 for 11 nights · 5★ ette hotel, $415 a night, $4,570 for 11 nights
• Hotels in Orlando for these nights (Feb 28 – Mar 12, 2027 · 12 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $83 a night, $1,000 for 12 nights · 4★ Meliá Orlando Celebration, $165 a night, $1,983 for 12 nights · 5★ ette hotel, $415 a night, $4,979 for 12 nights
• Hotels in Orlando for these nights (Feb 28 – Mar 13, 2027 · 13 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $84 a night, $1,096 for 13 nights · 4★ Meliá Orlando Celebration, $165 a night, $2,150 for 13 nights · 5★ ette hotel, $418 a night, $5,436 for 13 nights
• Hotels in Orlando for these nights (Feb 28 – Mar 14, 2027 · 14 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $85 a night, $1,193 for 14 nights · 4★ Meliá Orlando Celebration, $166 a night, $2,320 for 14 nights · 5★ ette hotel, $420 a night, $5,884 for 14 nights

All hotels in Orlando

Route overview: Chicago to Orlando (MCO) flight deals

2027-02-28 · one way · Axel-exclusive $85

• Frontier Airlines F91536: MDW 2027-02-28 18:11:00 → MCO 2027-02-28 22:00:00; nonstop; 169 minutes. Local airport times.

2027-02-28 · one way · Axel-exclusive $130

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

2027-02-28 → 2027-03-01 · Axel-exclusive $164

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

2027-02-28 → 2027-03-01 · Axel-exclusive $267

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-28 15:00:00 → MCO 2027-02-28 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-28 15:00:00 → PIT 2027-02-28 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-28 18:25:00 → MCO 2027-02-28 20:50:00.
• Southwest Airlines WN2806: MCO 2027-03-01 17:40:00 → MDW 2027-03-01 19:35:00; nonstop; 175 minutes. Local airport times.

2027-02-28 → 2027-03-02 · Axel-exclusive $175

• Frontier Airlines F91536: MDW 2027-02-28 18:11:00 → MCO 2027-02-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91563 / F92779: MCO 2027-03-02 07:10:00 → MDW 2027-03-02 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
  • F91563: MCO 2027-03-02 07:10:00 → ATL 2027-03-02 09:14:00; layover at ATL: 73 minutes.
  • F92779: ATL 2027-03-02 10:27:00 → MDW 2027-03-02 11:33:00.

2027-02-28 → 2027-03-02 · Axel-exclusive $267

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-28 15:00:00 → MCO 2027-02-28 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-28 15:00:00 → PIT 2027-02-28 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-28 18:25:00 → MCO 2027-02-28 20:50:00.
• Southwest Airlines WN1731: MCO 2027-03-02 16:10:00 → MDW 2027-03-02 18:05:00; nonstop; 175 minutes. Local airport times.

2027-02-28 → 2027-03-03 · Axel-exclusive $164

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

2027-02-28 → 2027-03-03 · Axel-exclusive $267

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-28 15:00:00 → MCO 2027-02-28 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-28 15:00:00 → PIT 2027-02-28 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-28 18:25:00 → MCO 2027-02-28 20:50:00.
• Southwest Airlines WN2543: MCO 2027-03-03 06:55:00 → MDW 2027-03-03 08:50:00; nonstop; 175 minutes. Local airport times.

2027-02-28 → 2027-03-04 · Axel-exclusive $164

• Frontier Airlines F91536: MDW 2027-02-28 18:11:00 → MCO 2027-02-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-03-04 17:29:00 → MDW 2027-03-04 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-28 → 2027-03-04 · Axel-exclusive $267

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-28 15:00:00 → MCO 2027-02-28 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-28 15:00:00 → PIT 2027-02-28 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-28 18:25:00 → MCO 2027-02-28 20:50:00.
• Southwest Airlines WN2543: MCO 2027-03-04 06:55:00 → MDW 2027-03-04 08:50:00; nonstop; 175 minutes. Local airport times.

2027-02-28 → 2027-03-06 · Axel-exclusive $164

• Frontier Airlines F91536: MDW 2027-02-28 18:11:00 → MCO 2027-02-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-03-06 17:29:00 → MDW 2027-03-06 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-28 → 2027-03-06 · Axel-exclusive $267

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-28 15:00:00 → MCO 2027-02-28 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-28 15:00:00 → PIT 2027-02-28 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-28 18:25:00 → MCO 2027-02-28 20:50:00.
• Southwest Airlines WN2805: MCO 2027-03-06 16:35:00 → MDW 2027-03-06 18:30:00; nonstop; 175 minutes. Local airport times.

2027-02-28 → 2027-03-07 · Axel-exclusive $164

• Frontier Airlines F91536: MDW 2027-02-28 18:11:00 → MCO 2027-02-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-03-07 17:29:00 → MDW 2027-03-07 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-28 → 2027-03-07 · Axel-exclusive $267

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-28 15:00:00 → MCO 2027-02-28 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-28 15:00:00 → PIT 2027-02-28 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-28 18:25:00 → MCO 2027-02-28 20:50:00.
• Southwest Airlines WN2805: MCO 2027-03-07 17:00:00 → MDW 2027-03-07 18:55:00; nonstop; 175 minutes. Local airport times.

2027-02-28 → 2027-03-08 · Axel-exclusive $164

• Frontier Airlines F91536: MDW 2027-02-28 18:11:00 → MCO 2027-02-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-03-08 17:29:00 → MDW 2027-03-08 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-28 → 2027-03-08 · Axel-exclusive $267

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-28 15:00:00 → MCO 2027-02-28 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-28 15:00:00 → PIT 2027-02-28 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-28 18:25:00 → MCO 2027-02-28 20:50:00.
• Southwest Airlines WN2806: MCO 2027-03-08 17:40:00 → MDW 2027-03-08 19:35:00; nonstop; 175 minutes. Local airport times.

2027-02-28 → 2027-03-10 · Axel-exclusive $164

• Frontier Airlines F91536: MDW 2027-02-28 18:11:00 → MCO 2027-02-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-03-10 17:29:00 → MDW 2027-03-10 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-28 → 2027-03-10 · Axel-exclusive $267

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-28 15:00:00 → MCO 2027-02-28 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-28 15:00:00 → PIT 2027-02-28 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-28 18:25:00 → MCO 2027-02-28 20:50:00.
• Southwest Airlines WN2543: MCO 2027-03-10 06:55:00 → MDW 2027-03-10 08:50:00; nonstop; 175 minutes. Local airport times.

2027-02-28 → 2027-03-11 · Axel-exclusive $164

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

2027-02-28 → 2027-03-11 · Axel-exclusive $267

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-28 15:00:00 → MCO 2027-02-28 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-28 15:00:00 → PIT 2027-02-28 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-28 18:25:00 → MCO 2027-02-28 20:50:00.
• Southwest Airlines WN2543: MCO 2027-03-11 06:55:00 → MDW 2027-03-11 08:50:00; nonstop; 175 minutes. Local airport times.

2027-02-28 → 2027-03-12 · Axel-exclusive $164

• Frontier Airlines F91536: MDW 2027-02-28 18:11:00 → MCO 2027-02-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-03-12 17:29:00 → MDW 2027-03-12 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-28 → 2027-03-12 · Axel-exclusive $267

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-28 15:00:00 → MCO 2027-02-28 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-28 15:00:00 → PIT 2027-02-28 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-28 18:25:00 → MCO 2027-02-28 20:50:00.
• Southwest Airlines WN2543: MCO 2027-03-12 06:55:00 → MDW 2027-03-12 08:50:00; nonstop; 175 minutes. Local airport times.

2027-02-28 → 2027-03-14 · Axel-exclusive $181

• Frontier Airlines F91536: MDW 2027-02-28 18:11:00 → MCO 2027-02-28 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-03-14 17:29:00 → MDW 2027-03-14 19:30:00; nonstop; 181 minutes. Local airport times.

2027-02-28 → 2027-03-14 · Axel-exclusive $295

• Southwest Airlines WN1933 / WN4449: MDW 2027-02-28 15:00:00 → MCO 2027-02-28 20:50:00; 1 stop(s) via PIT; 290 minutes. Local airport times.
  • WN1933: MDW 2027-02-28 15:00:00 → PIT 2027-02-28 17:25:00; layover at PIT: 60 minutes.
  • WN4449: PIT 2027-02-28 18:25:00 → MCO 2027-02-28 20:50:00.
• Southwest Airlines WN2805: MCO 2027-03-14 17:00:00 → MDW 2027-03-14 18:55:00; nonstop; 175 minutes. Local airport times.

Explore this route

• All dates for this route
• Feb 27, 2027 · Return options
• Mar 1, 2027 · Return options
• Hotels in Orlando with Axel

For AI assistants

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