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Winter Haven

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Winter Haven Flights as Low as $119

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

Frontier Airlines
Sat, Apr 25 - Mon, May 4
ORD
O'Hare Intl.
TPA
Tampa Intl.
$119 Roundtrip, found 4 hours ago
$119
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Apr 25 from O'Hare Intl. to Tampa Intl., returning Mon, May 4, priced at $119 found 4 hours ago
Spirit Airlines
Mon, Mar 23 - Sun, Mar 29
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$125 Roundtrip, just found
$125
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Mar 23 from Detroit Metropolitan Wayne County to Tampa Intl., returning Sun, Mar 29, priced at $125 just found
Frontier Airlines
Sat, Apr 25 - Mon, May 4
ORD
O'Hare Intl.
TPA
Tampa Intl.
$126 Roundtrip, found 4 hours ago
$126
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Apr 25 from O'Hare Intl. to Tampa Intl., returning Mon, May 4, priced at $126 found 4 hours ago
Spirit Airlines
Sat, Apr 25 - Mon, May 4
ORD
O'Hare Intl.
TPA
Tampa Intl.
$131 Roundtrip, found 4 hours ago
$131
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, Apr 25 from O'Hare Intl. to Tampa Intl., returning Mon, May 4, priced at $131 found 4 hours ago
Frontier Airlines
Sun, Apr 5 - Fri, Apr 24
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$131 Roundtrip, found 2 days ago
$131
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Apr 5 from Detroit Metropolitan Wayne County to Tampa Intl., returning Fri, Apr 24, priced at $131 found 2 days ago
Spirit Airlines
Wed, Apr 8 - Tue, Apr 14
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$133 Roundtrip, found 2 days ago
$133
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Apr 8 from Detroit Metropolitan Wayne County to Tampa Intl., returning Tue, Apr 14, priced at $133 found 2 days ago
Spirit Airlines
Sat, Apr 25 - Mon, May 4
ORD
O'Hare Intl.
TPA
Tampa Intl.
$135 Roundtrip, found 4 hours ago
$135
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, Apr 25 from O'Hare Intl. to Tampa Intl., returning Mon, May 4, priced at $135 found 4 hours ago
Spirit Airlines
Tue, Apr 7 - Tue, Apr 14
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$135 Roundtrip, found 6 hours ago
$135
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Tue, Apr 7 from Detroit Metropolitan Wayne County to Tampa Intl., returning Tue, Apr 14, priced at $135 found 6 hours ago
Frontier Airlines
Sun, May 10 - Sat, May 16
MSP
Minneapolis - St. Paul Intl.
TPA
Tampa Intl.
$166 Roundtrip, found 6 hours ago
$166
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sun, May 10 from Minneapolis - St. Paul Intl. to Tampa Intl., returning Sat, May 16, priced at $166 found 6 hours ago
Sun Country Airlines
Sun, May 10 - Fri, May 15
MSP
Minneapolis - St. Paul Intl.
TPA
Tampa Intl.
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Sun, May 10 from Minneapolis - St. Paul Intl. to Tampa Intl., returning Fri, May 15, priced at $193 found 1 day ago
Sun Country Airlines
Mon, Apr 13 - Thu, Apr 23
MSP
Minneapolis - St. Paul Intl.
PIE
St. Petersburg-Clearwater Intl.
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Sun Country Airlines flight, departing Mon, Apr 13 from Minneapolis - St. Paul Intl. to St. Petersburg-Clearwater Intl., returning Thu, Apr 23, priced at $197 found 4 days ago
Delta
Sat, Aug 29 - Sat, Sep 12
MSP
Minneapolis - St. Paul Intl.
TPA
Tampa Intl.
$219 Roundtrip, found 5 hours ago
$219
Roundtrip
found 5 hours ago
Select Delta flight, departing Sat, Aug 29 from Minneapolis - St. Paul Intl. to Tampa Intl., returning Sat, Sep 12, priced at $219 found 5 hours ago
United
Wed, May 6 - Sat, May 9
ORD
O'Hare Intl.
TPA
Tampa Intl.
$226 Roundtrip, found 21 hours ago
$226
Roundtrip
found 21 hours ago
Select United flight, departing Wed, May 6 from O'Hare Intl. to Tampa Intl., returning Sat, May 9, priced at $226 found 21 hours ago
American Airlines
Wed, May 6 - Sat, May 9
ORD
O'Hare Intl.
TPA
Tampa Intl.
$226 Roundtrip, found 21 hours ago
$226
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Wed, May 6 from O'Hare Intl. to Tampa Intl., returning Sat, May 9, priced at $226 found 21 hours ago
JetBlue Airways
Tue, Jun 2 - Mon, Jun 8
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$257 Roundtrip, found 6 hours ago
$257
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Tue, Jun 2 from Detroit Metropolitan Wayne County to Tampa Intl., returning Mon, Jun 8, priced at $257 found 6 hours ago
Alaska Airlines
Sat, May 9 - Fri, May 15
ORD
O'Hare Intl.
TPA
Tampa Intl.
$551 Roundtrip, found 1 day ago
$551
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sat, May 9 from O'Hare Intl. to Tampa Intl., returning Fri, May 15, priced at $551 found 1 day ago

Cheap Flights to Winter Haven

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

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

Frequently Asked Questions About flights to Winter Haven

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

What is the cheapest month to fly to Winter Haven?

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 Haven are in April, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winter Haven?

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 Haven.

What airport is best to fly into Winter Haven?

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

How much are flights to Winter Haven?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winter Haven on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $119, 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 Haven?

The trick to saving a stack of cash on your flight to Winter Haven? 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 $119 right now, why wait?

Winter Haven Flight Information
Destination airport
Tampa Intl.
Destination airport IATA code
TPA
Roundtrip price
$118

Last Minute Hotel Deals in Winter Haven

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Winter Haven FL
Stay at this motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.2/10 Good! (1,000 reviews)
I have been staying here the past couple of years but not anymore. The staff has been friendly and accommodating in the past, but no more. I made a special request of where I wanted my room and it's always been provided, the young man running the front desk seem to have a problem with this request. ...

Reviewed on Mar 20, 2026

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Howard Johnson by Wyndham Winter Haven FL
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
Stay at this hotel in Winter Haven. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions LEGOLAND® Florida and Peppa Pig Theme Park Florida ...
8.8/10 Excellent! (89 reviews)
Overall, we liked our stay. We enjoyed everything Lego and we made great memories. There are a few things that need serious improvement though, starting with the Bricks restaurant. For starters, we are extremely upset that we paid $100 for buffet style food that was clearly sitting there all day. ...

Reviewed on Mar 16, 2026

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Legoland Florida Hotel
LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

3 out of 5
100 Legoland Way SE Winter Haven FL
Stay at this hotel in Winter Haven. Enjoy free breakfast, parking (surcharge), and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Peppa Pig ...
9/10 Wonderful! (181 reviews)
Everything was nice and clean

Reviewed on Mar 17, 2026

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LEGOLAND Beach Retreat
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
8/10 Very Good! (9,208 reviews)
Clean and Staff

Reviewed on Mar 21, 2026

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The Grove Resort & Water Park Orlando
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Stay at this resort in Kissimmee. Enjoy free breakfast, free WiFi, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World ...
9.4/10 Exceptional! (3,186 reviews)
I’m

Reviewed on Mar 21, 2026

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Kompose Boutique Resort at Theme Parks
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

3 out of 5
2975 Arabian Nights Blvd Kissimmee FL
Book a stay at this family-friendly condo in Kissimmee. Enjoy free WiFi, 7 outdoor pools, and 7 hot tubs. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (3,683 reviews)
The resort is nice, practically new, it offers various pools and fully equipped and comfortable apartments. Unfortunately the check in was extremely slow the line was huge and took us around 40 mins to finally get to the check in counter. The line was huge and all guest had the same expression. Once ...

Reviewed on Mar 21, 2026

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Vacation Village Orlando, Celebration
Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

3 out of 5
7470 W. Irlo Bronson Memorial Hwy. Kissimmee FL
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff ...
8/10 Very Good! (3,895 reviews)
The room smelled moldy; housekeeping sprayed deodorizer. On the other hand, Mulligans was AWFUL. We walked in there in the evening on our first night for quick dinner and drinks. The waiter/bartender ignored us as we sat there for 15-20 minutes. Horrible customer service!! Missed out on a good tab ...

Reviewed on Mar 21, 2026

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Ramada by Wyndham Kissimmee Gateway
Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

3.5 out of 5
3011 Maingate Ln Kissimmee FL
Book a stay at this family-friendly hotel in Kissimmee. Enjoy free parking, 2 outdoor pools, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,423 reviews)
Didnt use the facilities

Reviewed on Mar 21, 2026

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Holiday Inn Resort Kissimmee by the Parks by IHG
See all 39,091 properties in Winter Haven
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.