$20 Cheap flight deals from Houston (HOU) to Winter Park (ORL)

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This Weekend's Flight Deals from Houston 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 4 - Tue, Oct 6
IAH
George Bush Intercontinental
MCO
Orlando Intl.
$403 Roundtrip, found 2 hours ago
$403
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Oct 4 from George Bush Intercontinental to Orlando Intl., returning Tue, Oct 6, priced at $403 found 2 hours ago
Sun, Oct 4 - Tue, Oct 6
IAH
George Bush Intercontinental
MCO
Orlando Intl.
$403 Roundtrip, found 2 hours ago
$403
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Oct 4 from George Bush Intercontinental to Orlando Intl., returning Tue, Oct 6, priced at $403 found 2 hours ago

Airfares from $20 One Way, $39 Round Trip from Houston to Winter Park

Prices starting at $39 for return flights and $20 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, Nov 16 - Sat, Nov 21
IAH
Houston
MCO
Orlando
$39 Roundtrip, found 6 hours ago
$39
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, Nov 16 from Houston to Orlando, returning Sat, Nov 21, priced at $39 found 6 hours ago
Sun, Nov 8 - Wed, Nov 11
IAH
Houston
MCO
Orlando
$52 Roundtrip, found 5 hours ago
$52
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sun, Nov 8 from Houston to Orlando, returning Wed, Nov 11, priced at $52 found 5 hours ago
Sat, Oct 24 - Sat, Oct 31
IAH
Houston
MCO
Orlando
$53 Roundtrip, found 1 hour ago
$53
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Oct 24 from Houston to Orlando, returning Sat, Oct 31, priced at $53 found 1 hour ago
Tue, Oct 27 - Wed, Oct 28
HOU
Houston
MCO
Orlando
$159 Roundtrip, found 5 days ago
$159
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Oct 27 from Houston to Orlando, returning Wed, Oct 28, priced at $159 found 5 days ago
Tue, Nov 3 - Sat, Nov 7
IAH
Houston
MCO
Orlando
$159 Roundtrip, found 18 hours ago
$159
Roundtrip
found 18 hours ago
Select United flight, departing Tue, Nov 3 from Houston to Orlando, returning Sat, Nov 7, priced at $159 found 18 hours ago

Winter Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Disney's Animal Kingdom Lodge
4.5-star property

Disney's Animal Kingdom Lodge

9/10 Wonderful! (1,003 reviews)

Nov 27 - Nov 29

2 night stay

Houston (HOU) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,283, price is now $746 per person
$746
per person
found 3 hours ago

Westgate Cocoa Beach Resort
4.0-star property

Westgate Cocoa Beach Resort

8.6/10 Excellent! (562 reviews)

Nov 7 - Nov 12

5 night stay

Houston (IAH) to Orlando (MCO)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,522, price is now $843 per person
$843
per person
found 1 day ago

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Winter Park first class flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

8.4/10 Very Good! (7,107 reviews)

Nov 23 - Nov 28

5 night stay

Houston (HOU) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,848, price is now $1,415 per person
$1,415
per person
found 3 hours ago

Margaritaville Cottages Orlando by Vstays with H2O Waterpark
4.0-star property

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

9.2/10 Wonderful! (1,003 reviews)

Nov 23 - Nov 28

5 night stay

Houston (HOU) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,536, price is now $1,773 per person
$1,773
per person
found 3 hours ago
We stayed in one of the cottages and it was just perfect. The fully equipped kitchen downstairs with a master suite was perfect for my parents. I appreciated having the laundry upstairs with the other bedrooms. The staff at the main building were so helpful with our packages and printing documents for us. Unfortunately we had a very busy week and could not enjoy the wonderful amenities of the resort. Overall, a great selection and would start again!

Reviewed on Sep 25, 2026

The Delaney Hotel
3.5-star property

The Delaney Hotel

9.6/10 Exceptional! (1,214 reviews)

Nov 23 - Nov 28

5 night stay

Houston (HOU) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,830, price is now $1,441 per person
$1,441
per person
found 3 hours ago

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More About Flying To Winter Park from Houston

Route Information for Flights from Houston to Winter Park

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

Houston 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.