Search Cheap Flights to
Winter Garden

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Winter Garden Flights as Low as $89

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

Breeze Airways
Sun, Aug 31 - Fri, Sep 12
BDL
Bradley Intl.
MCO
Orlando Intl.
$89 Roundtrip, found 1 day ago
$89
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Aug 31 from Bradley Intl. to Orlando Intl., returning Fri, Sep 12, priced at $89 found 1 day ago
Spirit Airlines
Sat, Aug 30 - Thu, Sep 4
BDL
Bradley Intl.
MCO
Orlando Intl.
$89 Roundtrip, found 15 hours ago
$89
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Sat, Aug 30 from Bradley Intl. to Orlando Intl., returning Thu, Sep 4, priced at $89 found 15 hours ago
Breeze Airways
Sun, Aug 31 - Fri, Sep 12
BDL
Bradley Intl.
MCO
Orlando Intl.
$94 Roundtrip, found 1 day ago
$94
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Aug 31 from Bradley Intl. to Orlando Intl., returning Fri, Sep 12, priced at $94 found 1 day ago
Spirit Airlines
Tue, Aug 19 - Wed, Sep 3
LGA
LaGuardia
MCO
Orlando Intl.
$94 Roundtrip, found 7 hours ago
$94
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Tue, Aug 19 from LaGuardia to Orlando Intl., returning Wed, Sep 3, priced at $94 found 7 hours ago
Breeze Airways
Sat, Aug 30 - Thu, Sep 4
BDL
Bradley Intl.
MCO
Orlando Intl.
$95 Roundtrip, found 15 hours ago
$95
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Sat, Aug 30 from Bradley Intl. to Orlando Intl., returning Thu, Sep 4, priced at $95 found 15 hours ago
Spirit Airlines
Sun, Aug 31 - Fri, Sep 12
BDL
Bradley Intl.
MCO
Orlando Intl.
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Aug 31 from Bradley Intl. to Orlando Intl., returning Fri, Sep 12, priced at $97 found 1 day ago
Breeze Airways
Sun, Aug 31 - Fri, Sep 12
BDL
Bradley Intl.
MCO
Orlando Intl.
$99 Roundtrip, found 1 day ago
$99
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Aug 31 from Bradley Intl. to Orlando Intl., returning Fri, Sep 12, priced at $99 found 1 day ago
Frontier Airlines
Sun, Sep 7 - Mon, Sep 8
BDL
Bradley Intl.
MCO
Orlando Intl.
$102 Roundtrip, found 5 days ago
$102
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Sep 7 from Bradley Intl. to Orlando Intl., returning Mon, Sep 8, priced at $102 found 5 days ago
Frontier Airlines
Tue, Sep 16 - Sat, Sep 20
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Sep 16 from John F. Kennedy Intl. to Orlando Intl., returning Sat, Sep 20, priced at $108 found 1 day ago
Breeze Airways
Sat, Aug 9 - Sat, Aug 16
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$118 Roundtrip, found 6 days ago
$118
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Aug 9 from Portsmouth Intl. to Orlando Intl., returning Sat, Aug 16, priced at $118 found 6 days ago
Spirit Airlines
Tue, Oct 28 - Tue, Oct 28
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$124 Roundtrip, just found
$124
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Oct 28 from Newark Liberty Intl. Airport to Orlando Intl., returning Tue, Oct 28, priced at $124 just found
Spirit Airlines
Thu, Sep 18 - Sun, Sep 21
BOS
Logan Intl.
MCO
Orlando Intl.
$130 Roundtrip, found 9 hours ago
$130
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Thu, Sep 18 from Logan Intl. to Orlando Intl., returning Sun, Sep 21, priced at $130 found 9 hours ago
United
Tue, Oct 28 - Tue, Oct 28
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$132 Roundtrip, just found
$132
Roundtrip
just found
Select United flight, departing Tue, Oct 28 from Newark Liberty Intl. Airport to Orlando Intl., returning Tue, Oct 28, priced at $132 just found
Delta
Sat, Sep 6 - Sat, Sep 6
LGA
LaGuardia
MCO
Orlando Intl.
$132 Roundtrip, found 14 hours ago
$132
Roundtrip
found 14 hours ago
Select Delta flight, departing Sat, Sep 6 from LaGuardia to Orlando Intl., returning Sat, Sep 6, priced at $132 found 14 hours ago
American Airlines
Sat, Sep 6 - Sat, Sep 6
LGA
LaGuardia
MCO
Orlando Intl.
$132 Roundtrip, found 14 hours ago
$132
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sat, Sep 6 from LaGuardia to Orlando Intl., returning Sat, Sep 6, priced at $132 found 14 hours ago
JetBlue Airways
Tue, Nov 11 - Sat, Nov 15
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$137 Roundtrip, found 2 hours ago
$137
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, Nov 11 from John F. Kennedy Intl. to Orlando Intl., returning Sat, Nov 15, priced at $137 found 2 hours ago

Cheap Flights to Winter Garden

Fall in love at first flight with your vacation to Winter Garden 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 Garden on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Winter Garden

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winter Garden 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 Garden?

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 Garden are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winter Garden?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Winter Garden.

What airport is best to fly into Winter Garden?

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

How much are flights to Winter Garden?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winter Garden on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $89, 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 Garden?

The trick to saving a stack of cash on your flight to Winter Garden? 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 $89 right now, why wait?

Winter Garden Flight Information
Destination airport
Orlando Intl.
Destination airport IATA code
MCO
Roundtrip price
$88

Last Minute Hotel Deals in Winter Garden

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
341 Flagler Ave, Winter Garden, FL
Stay at this 3-star business-friendly hotel in Winter Garden. Enjoy free breakfast, a free theme park shuttle, and a 24-hour fitness center. Our guests praise ...
9.2/10 Wonderful! (4,361 reviews)
"This is a great place to stay with family. I have also stayed by myself and have felt very safe. The property is wonderful, breakfast is great and the pool is really nice."

Reviewed on Jul 28, 2025

Get rates
Home2 Suites by Hilton Orlando at Flamingo Crossings
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Stay at this 4-star family-friendly resort in Four Corners. Enjoy 6 outdoor pools, 3 restaurants, and 2 hot tubs. Our guests praise the pool and the helpful ...
7.8/10 Good! (8,237 reviews)
"Beautiful and very clean resort! My kids had a great time lots of fun pool activities and slides for summer. We didn’t even need to leave the resort to have fun. The restaurant was great, and we loved the golf cart shuttles. Staff was super friendly and helpful. No complaints at all. I’d definitely ..."

Reviewed on Jul 28, 2025

Get rates
The Grove Resort & Water Park Orlando
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

2.5 out of 5
631 FLAGLER AVE, Winter Garden, FL
Book a stay at this business-friendly hotel in Winter Garden. Enjoy free breakfast, free WiFi, and a free theme park shuttle. Our guests praise the breakfast ...
9.4/10 Exceptional! (3,546 reviews)
"Great"

Reviewed on Jul 28, 2025

Get rates
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
411 Flagler Ave, Winter Garden, FL
Stay at this 3-star hotel in Winter Garden. Enjoy free breakfast, 2 bars/lounges, and a free theme park shuttle. Our guests praise the breakfast and the pool ...
9.4/10 Exceptional! (1,826 reviews)
"Felt like a very welcoming environment. Staff was great."

Reviewed on Jul 28, 2025

Get rates
Homewood Suites by Hilton Orlando at Flamingo Crossings
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

3 out of 5
2111 FLAGLER AVE, Winter Garden, FL
Stay at this 3-star business-friendly hotel in Winter Garden. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Our guests praise the breakfast and the pool ...
9.6/10 Exceptional! (1,701 reviews)
"Same food options for breakfast every morning. Front desk was absolutely amazing except for this one guy that told me I had to wait until housekeeping arrives before I could get toilet tissue. Overall, my family and I enjoyed our stay."

Reviewed on Jul 29, 2025

Get rates
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

4 out of 5
17777 Bali Blvd, Winter Garden, FL
Stay at this 4-star family-friendly hotel in Four Corners. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff ...
8.8/10 Excellent! (3,975 reviews)
"This was a short vacation - 3 nights with kids. The kids loved it! The water park was wonderful. They have a great bar and restaurant and ice-cream is available near the pool. Staff was extremely friendly and welcoming. They have a text message system which was great - If I needed something or had ..."

Reviewed on Jul 28, 2025

Get rates
Hilton Vacation Club Aqua Sol Orlando West
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
Stay at this 4-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.2/10 Very Good! (6,542 reviews)
"They have a number of food options, pillow beds for great comfort, and right across from universal!"

Reviewed on Jul 29, 2025

Get rates
DoubleTree by Hilton at the Entrance to Universal Orlando
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard, Orlando, FL
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
9.4/10 Exceptional! (3,419 reviews)
"Our stay at this hotel exceeded all expectations. From the moment we arrived, we were impressed by the elegant design and spacious layout of the property. The atmosphere feels upscale yet very welcoming, with beautifully maintained common areas that make it easy to relax and unwind. The location ..."

Reviewed on Jul 30, 2025

Get rates
Hyatt Regency Orlando International Airport
See all 53,879 properties in Winter Garden
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.