$54 Cheap flight deals from Cleveland (CLE) to Winter Park (ORL)

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This Weekend's Flight Deals from Cleveland to Winter Park

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, May 30 - Mon, Jun 1
CAK
Akron-Canton
MCO
Orlando Intl.
$188 Roundtrip, found 2 days ago
$188
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, May 30 from Akron-Canton to Orlando Intl., returning Mon, Jun 1, priced at $188 found 2 days ago
Fri, May 29 - Mon, Jun 1
CLE
Hopkins Intl.
MCO
Orlando Intl.
$243 Roundtrip, found 1 hour ago
$243
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, May 29 from Hopkins Intl. to Orlando Intl., returning Mon, Jun 1, priced at $243 found 1 hour ago

Airfares from $54 One Way, $97 Round Trip from Cleveland to Winter Park

Prices starting at $97 for return flights and $54 for one-way flights to Winter Park were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Aug 13 - Thu, Aug 27
CLE
Cleveland
MCO
Orlando
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Aug 13 from Cleveland to Orlando, returning Thu, Aug 27, priced at $97 found 3 days ago
Wed, Jul 1 - Thu, Jul 9
CLE
Cleveland
MCO
Orlando
$106 Roundtrip, found 6 days ago
$106
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Jul 1 from Cleveland to Orlando, returning Thu, Jul 9, priced at $106 found 6 days ago
Thu, Aug 13 - Thu, Aug 20
CLE
Cleveland
MCO
Orlando
$107 Roundtrip, found 4 days ago
$107
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Aug 13 from Cleveland to Orlando, returning Thu, Aug 20, priced at $107 found 4 days ago
Mon, Aug 24 - Thu, Aug 27
CAK
Akron
MCO
Orlando
$112 Roundtrip, found 12 hours ago
$112
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Mon, Aug 24 from Akron to Orlando, returning Thu, Aug 27, priced at $112 found 12 hours ago
Tue, Aug 4 - Tue, Aug 11
CLE
Cleveland
MCO
Orlando
$287 Roundtrip, found 4 hours ago
$287
Roundtrip
found 4 hours ago
Select United flight, departing Tue, Aug 4 from Cleveland to Orlando, returning Tue, Aug 11, priced at $287 found 4 hours ago

Winter Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Boardwalk Inn and Suites
2.5-star property

Boardwalk Inn and Suites

8.4/10 Very Good! (1,839 reviews)

Jul 7 - Jul 14

7 night stay

Cleveland (CLE) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $791, price is now $460 per person
$460
per person
found 6 hours ago
Absolutely fantastic.

Reviewed on Feb 9, 2026

Westgate Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

8.8/10 Excellent! (1,250 reviews)

Jun 25 - Jun 28

3 night stay

Cleveland (CLE) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $975, price is now $480 per person
$480
per person
found 23 hours ago
The property is nice and convenient. I took a star off because my whole party agreed that the beds were not comfortable. I don’t remember a worse mattress. Other than that, great place that was clean and spacious. Great shower pressure.

Reviewed on Apr 3, 2026

The Shores Resort & Spa
4.0-star property

The Shores Resort & Spa

9/10 Wonderful! (1,819 reviews)

Jul 7 - Jul 14

7 night stay

Cleveland (CLE) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,093, price is now $614 per person
$614
per person
found 6 hours ago
Fantastic hotel with incredible view. Arcade fun and gym nice! S’mores outside an added touch. Restaurant fantastic! We’ll be back.

Reviewed on Apr 17, 2026

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More About Flying To Winter Park from Cleveland

Route Information for Flights from Cleveland to Winter Park

Origin Airport IATA Code
CLE
Destination Airport IATA Code
ORL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Cleveland to Winter Park

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.