$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.

Sat, Jan 10 - Sat, Jan 17
CLE
Hopkins Intl.
MCO
Orlando Intl.
$96 Roundtrip, just found
$96
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jan 10 from Hopkins Intl. to Orlando Intl., returning Sat, Jan 17, priced at $96 just found
Sat, Jan 10 - Thu, Jan 15
CAK
Akron-Canton
MCO
Orlando Intl.
$113 Roundtrip, found 20 hours ago
$113
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Sat, Jan 10 from Akron-Canton to Orlando Intl., returning Thu, Jan 15, priced at $113 found 20 hours ago

Airfares from $29 One Way, $59 Round Trip from Cleveland to Winter Park

Prices starting at $59 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.

Sat, Feb 7 - Sat, Feb 14
CLE
Cleveland
MCO
Orlando
$59 Roundtrip, found 10 hours ago
$59
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sat, Feb 7 from Cleveland to Orlando, returning Sat, Feb 14, priced at $59 found 10 hours ago
Sat, Feb 21 - Tue, Mar 3
CLE
Cleveland
MCO
Orlando
$59 Roundtrip, found 1 hour ago
$59
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Feb 21 from Cleveland to Orlando, returning Tue, Mar 3, priced at $59 found 1 hour ago
Sat, Jan 31 - Sat, Feb 7
CLE
Cleveland
MCO
Orlando
$62 Roundtrip, found 1 hour ago
$62
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jan 31 from Cleveland to Orlando, returning Sat, Feb 7, priced at $62 found 1 hour ago
Tue, Feb 3 - Thu, Feb 12
CAK
Akron
MCO
Orlando
$102 Roundtrip, found 4 hours ago
$102
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Tue, Feb 3 from Akron to Orlando, returning Thu, Feb 12, priced at $102 found 4 hours ago
Sat, Feb 7 - Sat, Feb 14
CLE
Cleveland
MCO
Orlando
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Feb 7 from Cleveland to Orlando, returning Sat, Feb 14, priced at $159 found 1 day ago

Winter Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
2.0-star property

Seasons Florida Resort

8.8/10 Excellent! (3,229 reviews)

Feb 4 - Feb 8

4 night stay

Cleveland (CLE) to Orlando (MCO)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $444, price is now $262 per person
$262
per person
found 1 day ago
Nice room, very clean, friendly staff. They didn't have breakfast that why I'm giving 4 star

Reviewed on Jan 2, 2026

Boardwalk Inn and Suites
2.5-star property

Boardwalk Inn and Suites

8.4/10 Very Good! (1,533 reviews)

Feb 27 - Mar 1

2 night stay

Cleveland (CLE) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $767, price is now $446 per person
$446
per person
found 1 day ago
Nice room, liked pool and spa. At this location unfortunately no breakfast and no breakfast restaurants nearby.

Reviewed on Dec 3, 2025

The Shores Resort & Spa
4.0-star property

The Shores Resort & Spa

9/10 Wonderful! (1,681 reviews)

Feb 27 - Mar 1

2 night stay

Cleveland (CLE) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $607, price is now $354 per person
$354
per person
found 1 day ago
Pretty hotel with nice layout and nice rooms. Great restaurant and friendly staff.

Reviewed on Sep 20, 2025

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Winter Park packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Sonesta Essential Orlando Airport
3.0-star property

Sonesta Essential Orlando Airport

7.2/10 Good! (1,171 reviews)

Feb 12 - Feb 15

3 night stay

Cleveland (CLE) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $843, price is now $765 per person
$765
per person
found 3 hours ago
Cooooooozy bed!!!!! Great sweet front desk girl!!!!! Great deal for the price!! I had a one night layover and it was perfect!!!

Reviewed on Dec 14, 2025

The Delaney Hotel
3.5-star property

The Delaney Hotel

9.6/10 Exceptional! (1,002 reviews)

Feb 12 - Feb 15

3 night stay

Cleveland (CLE) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,148, price is now $920 per person
$920
per person
found 3 hours ago
Great location for hospital access

Reviewed on Jul 8, 2025

Vista Cay by Orlando Resort Rentals on Universal Boulevard
3.5-star property

Vista Cay by Orlando Resort Rentals on Universal Boulevard

9.4/10 Exceptional! (843 reviews)

Feb 12 - Feb 15

3 night stay

Cleveland (CLE) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,220, price is now $1,007 per person
$1,007
per person
found 3 hours ago
excellente!! lo mejor!!

Reviewed on Sep 27, 2024

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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.