$28 Cheap flight deals from Hagerstown (DCA) 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 Hagerstown 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, Jan 25 - Mon, Jan 26
IAD
Washington Dulles Intl.
MCO
Orlando Intl.
$136 Roundtrip, just found
$136
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Jan 25 from Washington Dulles Intl. to Orlando Intl., returning Mon, Jan 26, priced at $136 just found
Sun, Jan 25 - Mon, Jan 26
BWI
Baltimore Washington Intl. Thurgood Marshall
MCO
Orlando Intl.
$223 Roundtrip, just found
$223
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Jan 25 from Baltimore Washington Intl. Thurgood Marshall to Orlando Intl., returning Mon, Jan 26, priced at $223 just found
Sat, Jan 24 - Thu, Jan 29
DCA
Ronald Reagan Washington National
MCO
Orlando Intl.
$245 Roundtrip, found 1 hour ago
$245
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jan 24 from Ronald Reagan Washington National to Orlando Intl., returning Thu, Jan 29, priced at $245 found 1 hour ago

Airfares from $28 One Way, $56 Round Trip from Hagerstown to Winter Park

Prices starting at $56 for return flights and $28 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.

Sun, Feb 1 - Fri, Feb 6
IAD
Washington
MCO
Orlando
$56 Roundtrip, found 1 hour ago
$56
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Feb 1 from Washington to Orlando, returning Fri, Feb 6, priced at $56 found 1 hour ago
Tue, Mar 3 - Wed, Mar 4
BWI
Baltimore
MCO
Orlando
$66 Roundtrip, found 4 days ago
$66
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Mar 3 from Baltimore to Orlando, returning Wed, Mar 4, priced at $66 found 4 days ago
Sat, Feb 28 - Wed, Mar 4
BWI
Baltimore
MCO
Orlando
$73 Roundtrip, found 6 hours ago
$73
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Sat, Feb 28 from Baltimore to Orlando, returning Wed, Mar 4, priced at $73 found 6 hours ago
Mon, Feb 23 - Fri, Mar 6
IAD
Washington
MCO
Orlando
$80 Roundtrip, found 13 hours ago
$80
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Mon, Feb 23 from Washington to Orlando, returning Fri, Mar 6, priced at $80 found 13 hours ago
Sat, Mar 21 - Sat, Mar 28
DCA
Washington
MCO
Orlando
$116 Roundtrip, found 2 hours ago
$116
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sat, Mar 21 from Washington to Orlando, returning Sat, Mar 28, priced at $116 found 2 hours 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)

Mar 14 - Mar 19

5 night stay

Baltimore (BWI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $495, price is now $278 per person
$278
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

Palazzo Lakeside Hotel
3.0-star property

Palazzo Lakeside Hotel

8.2/10 Very Good! (5,145 reviews)

Mar 14 - Mar 19

5 night stay

Baltimore (BWI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Price was $1,105, price is now $302 per person
$302
per person
found 1 day ago
Henry, front desk clerk, was exceptional with checking us in.

Reviewed on Dec 27, 2025

CoCo Key Hotel and Water Resort 
3.5-star property

CoCo Key Hotel and Water Resort 

8/10 Very Good! (3,666 reviews)

Mar 14 - Mar 19

5 night stay

Baltimore (BWI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $529, price is now $292 per person
$292
per person
found 1 day ago
My wife didn't really care for the place! Pool area was the best part about this place.

Reviewed on Dec 2, 2025

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

Winter Park packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Lake Buena Vista Resort Village & Spa
4.0-star property

Lake Buena Vista Resort Village & Spa

8.4/10 Very Good! (9,283 reviews)

Mar 8 - Mar 14

6 night stay

Washington (WAS) to Orlando (MCO)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,341, price is now $901 per person
$901
per person
found 1 day ago
So we had a good vacation, and the room was spacious, however, there were roaches. I told the front desk and they said oh my gosh, we will clean it, but didn’t offer to move me. We did have a good vacation, but I was a little worried when I went to sleep that roaches would get in my stuff

Reviewed on Dec 15, 2025

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

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

9.2/10 Wonderful! (1,001 reviews)

Mar 8 - Mar 14

6 night stay

Washington (WAS) to Orlando (MCO)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,973, price is now $1,423 per person
$1,423
per person
found 1 day ago
We were very displeased with the cleanliness of our cottage upon arrival. I found multiple hairs on the ground and furniture, so vacuumed Before I even unpacked my suitcase. At the end of the night, our feet were so filthy dirty, we had to wash them before we could get into bed because the floors werent clean. The pool was gross, even had a used band aid in it. The kitchen barely had enough dishes and they left nothing to help with cooking coffee or anything. We've had many vrbo properties in the past, and this was one of the least desirable that we've stayed at.

Reviewed on Oct 7, 2024

Evermore Orlando Resort
4.0-star property

Evermore Orlando Resort

9.6/10 Exceptional! (489 reviews)

Mar 8 - Mar 14

6 night stay

Washington (WAS) to Orlando (MCO)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,527, price is now $2,625 per person
$2,625
per person
found 1 day ago
Amazing for families visting Orlando.

Reviewed on Oct 24, 2025

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

Winter Park first class flight packages

Price found within the past 48 hours. Click for updated prices.
Lake Buena Vista Resort Village & Spa
4.0-star property

Lake Buena Vista Resort Village & Spa

8.4/10 Very Good! (9,283 reviews)

Mar 8 - Mar 15

7 night stay

Baltimore (BWI) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,081, price is now $1,557 per person
$1,557
per person
found 1 day ago
So we had a good vacation, and the room was spacious, however, there were roaches. I told the front desk and they said oh my gosh, we will clean it, but didn’t offer to move me. We did have a good vacation, but I was a little worried when I went to sleep that roaches would get in my stuff

Reviewed on Dec 15, 2025

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

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

9.2/10 Wonderful! (1,001 reviews)

Mar 8 - Mar 15

7 night stay

Baltimore (BWI) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,870, price is now $2,195 per person
$2,195
per person
found 1 day ago
We were very displeased with the cleanliness of our cottage upon arrival. I found multiple hairs on the ground and furniture, so vacuumed Before I even unpacked my suitcase. At the end of the night, our feet were so filthy dirty, we had to wash them before we could get into bed because the floors werent clean. The pool was gross, even had a used band aid in it. The kitchen barely had enough dishes and they left nothing to help with cooking coffee or anything. We've had many vrbo properties in the past, and this was one of the least desirable that we've stayed at.

Reviewed on Oct 7, 2024

Evermore Orlando Resort
4.0-star property

Evermore Orlando Resort

9.6/10 Exceptional! (489 reviews)

Mar 8 - Mar 15

7 night stay

Baltimore (BWI) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,591, price is now $3,539 per person
$3,539
per person
found 1 day ago
Amazing for families visting Orlando.

Reviewed on Oct 24, 2025

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

More About Flying To Winter Park from Hagerstown

Route Information for Flights from Hagerstown to Winter Park

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

Hagerstown to Winter Park

Orbitz is the number one travel site for finding guaranteed low prices on Hagerstown to Winter Park flights. Not only do we have discount tickets on domestic and international tickets but our cutting-edge mobile tools keep you informed on the go.

Find Low Prices in One Place

Booking a trip from Hagerstown to Winter Park has never been easier. Not only will you find great deals on flights, we offer bargains on cruises, car rentals, top-notch hotels, and more. You can also research and add local activities in Winter Park to your flight or hotel reservation to keep the kids happy and active.

Flight Booking, Alerts, and More on Your Mobile Device

Use our mobile app for your iPhone, iPad, or Android phone—or our mobile website m.orbitz.com—to find bargains on flights from Hagerstown to Winter Park wherever you are. Book your cheap Hagerstown to Winter Park flights and a hotel room too—even at the last minute. Orbitz also makes your life easier with free alerts that are sent to your mobile phone or email about delays to your upcoming flights from Hagerstown to Winter Park.

Don’t Miss out on Miles

Accumulate frequent flyer miles or points on your Hagerstown to Winter Park flights. It’s as simple as entering your frequent flyer number when you’re making your flight reservation on Orbitz to rack up miles on qualified flights from Hagerstown to Winter Park. You can save your frequent flyer numbers in your Orbitz account to save time during your next flight booking.

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.