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Winter Park

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Winter Park Flights as Low as $102

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Allegiant Air
Thu, Jan 21 - Thu, Jan 28
PSM
Portsmouth Intl.
SFB
Orlando Sanford Intl.
$102 Roundtrip, found 5 hours ago
$102
Roundtrip
found 5 hours ago
Select Allegiant Air flight, departing Thu, Jan 21 from Portsmouth Intl. to Orlando Sanford Intl., returning Thu, Jan 28, priced at $102 found 5 hours ago
Allegiant Air
Thu, Jan 21 - Thu, Jan 28
PSM
Portsmouth Intl.
SFB
Orlando Sanford Intl.
$110 Roundtrip, found 1 hour ago
$110
Roundtrip
found 1 hour ago
Select Allegiant Air flight, departing Thu, Jan 21 from Portsmouth Intl. to Orlando Sanford Intl., returning Thu, Jan 28, priced at $110 found 1 hour ago
Allegiant Air
Tue, Jan 5 - Thu, Jan 14
GRR
Gerald R. Ford Intl.
SFB
Orlando Sanford Intl.
$114 Roundtrip, found 6 hours ago
$114
Roundtrip
found 6 hours ago
Select Allegiant Air flight, departing Tue, Jan 5 from Gerald R. Ford Intl. to Orlando Sanford Intl., returning Thu, Jan 14, priced at $114 found 6 hours ago
Allegiant Air
Fri, Dec 4 - Mon, Dec 7
CHA
Chattanooga Metropolitan
SFB
Orlando Sanford Intl.
$124 Roundtrip, found 1 day ago
$124
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Fri, Dec 4 from Chattanooga Metropolitan to Orlando Sanford Intl., returning Mon, Dec 7, priced at $124 found 1 day ago
Frontier Airlines
Thu, Nov 26 - Thu, Dec 3
GRR
Gerald R. Ford Intl.
MCO
Orlando Intl.
$145 Roundtrip, found 6 hours ago
$145
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, Nov 26 from Gerald R. Ford Intl. to Orlando Intl., returning Thu, Dec 3, priced at $145 found 6 hours ago
Allegiant Air
Sun, Dec 6 - Thu, Dec 10
BLV
MidAmerica-St. Louis
SFB
Orlando Sanford Intl.
$148 Roundtrip, found 19 hours ago
$148
Roundtrip
found 19 hours ago
Select Allegiant Air flight, departing Sun, Dec 6 from MidAmerica-St. Louis to Orlando Sanford Intl., returning Thu, Dec 10, priced at $148 found 19 hours ago
Breeze Airways
Thu, Jan 7 - Thu, Jan 14
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$184 Roundtrip, just found
$184
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Jan 7 from Portsmouth Intl. to Orlando Intl., returning Thu, Jan 14, priced at $184 just found
Arajet
Sun, Jun 6 - Sun, Jun 13
PUJ
Punta Cana Intl.
SFB
Orlando Sanford Intl.
$298 Roundtrip, found 1 day ago
$298
Roundtrip
found 1 day ago
Select Arajet flight, departing Sun, Jun 6 from Punta Cana Intl. to Orlando Sanford Intl., returning Sun, Jun 13, priced at $298 found 1 day ago
Bargain Flight
Wed, Jan 13 - Sat, Jan 16
GRR
Gerald R. Ford Intl.
MCO
Orlando Intl.
$308 Roundtrip, found 5 hours ago
$308
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Wed, Jan 13 from Gerald R. Ford Intl. to Orlando Intl., returning Sat, Jan 16, priced at $308 found 5 hours ago
Delta
Wed, Jan 13 - Wed, Jan 13
GRR
Gerald R. Ford Intl.
MCO
Orlando Intl.
$369 Roundtrip, found 6 hours ago
$369
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed, Jan 13 from Gerald R. Ford Intl. to Orlando Intl., returning Wed, Jan 13, priced at $369 found 6 hours ago
Southwest Airlines
Wed, Jan 13 - Sat, Jan 16
GRR
Gerald R. Ford Intl.
MCO
Orlando Intl.
$369 Roundtrip, found 5 hours ago
$369
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Jan 13 from Gerald R. Ford Intl. to Orlando Intl., returning Sat, Jan 16, priced at $369 found 5 hours ago
United
Thu, Dec 31 - Wed, Jan 6
CHA
Chattanooga Metropolitan
MCO
Orlando Intl.
$379 Roundtrip, found 6 hours ago
$379
Roundtrip
found 6 hours ago
Select United flight, departing Thu, Dec 31 from Chattanooga Metropolitan to Orlando Intl., returning Wed, Jan 6, priced at $379 found 6 hours ago
Frontier Airlines
Fri, Jan 22 - Tue, Jan 26
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$390 Roundtrip, found 5 hours ago
$390
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Jan 22 from Punta Cana Intl. to Orlando Intl., returning Tue, Jan 26, priced at $390 found 5 hours ago
American Airlines
Wed, Jan 13 - Sat, Jan 16
GRR
Gerald R. Ford Intl.
MCO
Orlando Intl.
$499 Roundtrip, found 5 hours ago
$499
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, Jan 13 from Gerald R. Ford Intl. to Orlando Intl., returning Sat, Jan 16, priced at $499 found 5 hours ago
JetBlue Airways
Sat, Dec 19 - Sat, Jan 2
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$550 Roundtrip, just found
$550
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Dec 19 from Punta Cana Intl. to Orlando Intl., returning Sat, Jan 2, priced at $550 just found
Copa
Sun, Dec 6 - Thu, Dec 24
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$642 Roundtrip, found 1 day ago
$642
Roundtrip
found 1 day ago
Select Copa flight, departing Sun, Dec 6 from Punta Cana Intl. to Orlando Intl., returning Thu, Dec 24, priced at $642 found 1 day ago

Cheap Flights to Winter Park

Fall in love at first flight with your vacation to Winter Park by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Winter Park on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Winter Park, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Winter Park

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winter Park with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the ORL airport.

What is the cheapest month to fly to Winter Park?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Winter Park are in January, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winter Park?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Winter Park.

What airport is best to fly into Winter Park?

When you’re planning your trip to Winter Park, convenience is the name of the game. Luckily, Winter Park Orlando Intl. Airport is nearby so you can deplane and get going on checking off everything on your Winter Park must-do list.

How much are flights to Winter Park?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winter Park on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $102, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Winter Park?

The trick to saving a stack of cash on your flight to Winter Park? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $102 right now, why wait?

Winter Park Flight Information
Destination airport
Orlando Intl.
Destination airport IATA code
MCO
Roundtrip price
$38

Last Minute Hotel Deals in Winter Park

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard Orlando FL
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
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Hyatt Regency Orlando International Airport
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (7,340 reviews)
"The value for the stay for our Disney trip was excellent. We really loved everything about the room and the facilities. The room was huge and amazing for the price. Had plenty of amenities. Having two separate rooms for the kids and a full size living space was clutch with all the stuff we had for ..."

Reviewed on Nov 15, 2026

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Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista Orlando FL
Book a stay at this spa aparthotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (5,458 reviews)
"Everything was perfect!!"

Reviewed on Nov 15, 2026

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Marriott's Grande Vista
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd Orlando FL
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.6/10 Excellent! (7,213 reviews)
"Fabulous staff"

Reviewed on Nov 15, 2026

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DoubleTree by Hilton at the Entrance to Universal Orlando
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
9500 Turkey Lake Rd Orlando FL
Book a stay at this spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.4/10 Very Good! (7,333 reviews)
"I will never stay at a westgate again between the roach I found in my bathroom to the excessively over charge of amenities that we didn't use because they charge for amenities an charge to access the amenities also the faa grounded flights out an had to extend my stay they still charged me an additional ..."

Reviewed on Nov 15, 2026

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Westgate Lakes Resort & Spa Universal Studios Area
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

4 out of 5
12401 International Dr Orlando FL
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
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Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way Orlando FL
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (7,878 reviews)
"All in all, I would classify this as a decent day. I wish that I was notified prior to that one of the parks was going to be closed for winter and they would be doing repairs, as I was woken up very early in the morning by construction. Other than that, I completely love the hotel and would recommend ..."

Reviewed on Nov 15, 2026

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Universal's Cabana Bay Beach Resort
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

4 out of 5
2000 Hotel Plaza Boulevard Lake Buena Vista FL
Book a stay at this business-friendly hotel in Lake Buena Vista. Enjoy free breakfast, free WiFi, and 3 restaurants. Our guests praise the breakfast and the ...
9.8/10 Exceptional! (6,259 reviews)
"The staff were super nice and beyond friendly. From maintenance to front desk to the shuttle drivers. They seemed genuinely nice and naturally friendly. The view from the room we had of the fireworks was a 10 out of 10. The buffet food for breakfast and kickback was very decent that I was surprised. ..."

Reviewed on Nov 15, 2026

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Drury Plaza Hotel Orlando - Disney Springs Area
See all 16,807 properties in Winter Park
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.