$49 Cheap flight deals from Cleveland (CLE) to Winter Park (ORL)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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.

Sun, Oct 5 - Tue, Oct 7
CAK
Akron-Canton
MCO
Orlando Intl.
$212 Roundtrip, found 6 hours ago
$212
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sun, Oct 5 from Akron-Canton to Orlando Intl., returning Tue, Oct 7, priced at $212 found 6 hours ago
Fri, Oct 3 - Sun, Oct 5
CLE
Hopkins Intl.
MCO
Orlando Intl.
$258 Roundtrip, just found
$258
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Oct 3 from Hopkins Intl. to Orlando Intl., returning Sun, Oct 5, priced at $258 just found

Airfares from $49 One Way, $100 Round Trip from Cleveland to Winter Park

Prices starting at $100 for return flights and $49 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.

Mon, Oct 27 - Thu, Oct 30
CLE
Cleveland
MCO
Orlando
$100 Roundtrip, just found
$100
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Oct 27 from Cleveland to Orlando, returning Thu, Oct 30, priced at $100 just found
Tue, Nov 4 - Fri, Nov 7
CAK
Akron
MCO
Orlando
$102 Roundtrip, found 21 hours ago
$102
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Tue, Nov 4 from Akron to Orlando, returning Fri, Nov 7, priced at $102 found 21 hours ago
Mon, Oct 20 - Wed, Oct 22
CAK
Akron
MCO
Orlando
$103 Roundtrip, found 1 day ago
$103
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Oct 20 from Akron to Orlando, returning Wed, Oct 22, priced at $103 found 1 day ago
Wed, Nov 19 - Thu, Nov 27
CLE
Cleveland
MCO
Orlando
$103 Roundtrip, found 8 hours ago
$103
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Nov 19 from Cleveland to Orlando, returning Thu, Nov 27, priced at $103 found 8 hours ago
Sat, Nov 1 - Thu, Nov 6
CLE
Cleveland
MCO
Orlando
$149 Roundtrip, found 8 hours ago
$149
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Sat, Nov 1 from Cleveland to Orlando, returning Thu, Nov 6, priced at $149 found 8 hours ago

Winter Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
3.0-star property

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

8/10 Very Good! (122 reviews)

Nov 1 - Nov 4

3 night stay

Cleveland (CLE) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Cleveland (CLE)

Southwest Airlines • Coach
Save 100% on your flight
Price was $503, price is now $301 per person
$301
per person
found 1 day ago
The staff were super nice especially the lady at the front desk and the lady around the cocktail area. The hotel was nice and clean with a nice view it was walkable to Icon park and restaurants. Will stay there again.

Reviewed on Jul 31, 2025

Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8/10 Very Good! (1,360 reviews)

Nov 3 - Nov 10

7 night stay

Cleveland (CLE) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $882, price is now $490 per person
$490
per person
found 1 day ago
We took our 3 year old nephew here and he had a BLAST! There is so much to do, we didn’t leave for 2 of the 3 days that we stayed. He’s about 42 inches which got him on most of the slides but not all. Keep size in mind when booking for little ones because if they’re under 40in they’re limited to the slides. He was a little bummed that he couldn’t do the pirates plunge (biggest slide) but there were enough distractions that it didn’t matter. Also, the lazy river is great! Just be careful with the big kids, they tend to knock the little ones over or into the wall because they’re just running through it. The water park is an extra fee FYI There’s “ice” skating, swan paddle boats, water park, mini golf, a train trolly, restaurants, arcade, jungle gym, multiple pools. Definitely a good spot if you don’t want to do the parks every day that you’re there! Highly recommend.

Reviewed on Apr 6, 2025

Casa Monica Resort & Spa, Autograph Collection
4.0-star property

Casa Monica Resort & Spa, Autograph Collection

9/10 Wonderful! (1,006 reviews)

Nov 6 - Nov 10

4 night stay

Cleveland (CLE) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,075, price is now $675 per person
$675
per person
found 1 day ago
Indifferent front staff.

Reviewed on Dec 25, 2024

Don't see what you're looking for?
See all available trips from Cleveland to Winter Park
View all trips

Winter Park packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel
3.0-star property

Palazzo Lakeside Hotel

8.2/10 Very Good! (5,176 reviews)

Nov 21 - Nov 23

2 night stay

Cleveland (CLE) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $640, price is now $558 per person
$558
per person
found 24 hours ago
The property itself was nice. The surrounding area was quite busy.

Reviewed on Jul 19, 2025

Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

8.2/10 Very Good! (5,346 reviews)

Nov 21 - Nov 23

2 night stay

Cleveland (CLE) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $806, price is now $634 per person
$634
per person
found 24 hours ago
It was ok for the price

Reviewed on Sep 27, 2025

DoubleTree by Hilton Orlando Airport
4.0-star property

DoubleTree by Hilton Orlando Airport

8.6/10 Excellent! (1,752 reviews)

Nov 21 - Nov 23

2 night stay

Cleveland (CLE) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $738, price is now $635 per person
$635
per person
found 24 hours ago
Our first room smelled like mold and front desk was extremely helpful and switched us right away!

Reviewed on Sep 28, 2025

Don't see what you're looking for?
See all available trips from Cleveland to Winter Park
View all trips

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

If you are looking to find the best deals on Cleveland to Winter Park flights, look no further than Orbitz. Orbitz offers guaranteed low prices as well as cutting-edge mobile tools to help you book cheap flights from Cleveland to Winter Park.

Mobile Apps Make Life Easier

Our mobile apps for Android and iPhone phones as well as tablets and iPads let you find the cheapest flights from Cleveland to Winter Park—whether you are at home or running errands. Use the apps to also keep track of delays to your Cleveland to Winter Park flights and baggage claim information.

Get Miles for Your Flights From Cleveland to Winter Park

It’s easy to earn points or miles for your frequent flyer or airline loyalty program on qualifying Cleveland to Winter Park flights with Orbitz. You can add your frequent flyer number to your online flight booking, and even store your numbers in your Orbitz account profile so they automatically get added the next time you book a flight.

Stay Informed While You Travel

Orbitz keeps you updated on information that’s relevant to your flights from Cleveland to Winter Park. We can send you and six of your personal contacts free travel alerts via SMS text, voicemail, or email, so you instantly know about flight delays or changes.

Keep More Money in Your Pocket With Discount Flights

Orbitz looks for the best deals on Cleveland to Winter Park flights for you. Mix and match airlines for your departing and return flights to fit your travel schedule and budget.

More Destinations

More Destinations

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.