$29 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.
Airfares from $29 One Way, $58 Round Trip from Cleveland to Winter Park
Prices starting at $58 for return flights and $29 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.
Winter Park economy flight packages
Palazzo Lakeside Hotel
Feb 15 - Feb 17
Cleveland (CLE) to Orlando (MCO)
Reviewed on Dec 27, 2025
Westgate Leisure Resort
Feb 17 - Feb 21
Cleveland (CLE) to Orlando (MCO)
Orlando (MCO) to Cleveland (CLE)
Reviewed on Mar 11, 2025
Florida Hotel & Conference Center in the Florida Mall
Feb 27 - Mar 5
Cleveland (CLE) to Orlando (MCO)
Reviewed on Dec 9, 2025
More About Flying To Winter Park from Cleveland
Route Information for Flights from Cleveland to Winter Park
Origin Airport IATA Code | CLE |
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Destination Airport IATA Code | ORL |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Cleveland to Winter Park
Looking for cheap Cleveland to Winter Park flights? Orbitz has the cheapest air fares for flights from Cleveland to Winter Park. Plus, with our cutting-edge mobile tools, travel planning has never been easier or more wallet-friendly.
Mobile Deals and Steals
Orbitz is dedicated to providing low fares on Cleveland to Winter Park flights. Now you can find the latest deals on-the-go with Orbitz’s mobile apps for iPhone, iPad, Android phones, and tablets. Instantly see discounted rates for hotels, cruises, vacations, and air tickets for a great vacation.
Book Hotels With Confidence
When you’re looking for hotel rooms to go with your bargain flights from Cleveland to Winter Park, Orbitz provides you descriptions, photos, reviews, and location maps so you know exactly what you are booking. With easy-to-use Orbitz map tools, you can search for nearby hotels on your mobile device.
Access Your Flight Information Anytime
Use the Orbitz app or the mobile Orbitz site, m.orbtiz.com, to see information about your Cleveland to Winter Park flights anytime you need it. Your itinerary is also sent to your email address for reference. Access updates on your flights from Cleveland to Winter Park on your mobile device too, including delays and baggage claim details.
Cheap Air Ticket Prices Guaranteed
Orbitz is your number one source for low fares for Cleveland to Winter Park flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to Winter Park. Need hotels too? You can book them last minute on your mobile phone.
Flights from Cleveland
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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.