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Winter Haven

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Winter Haven Flights as Low as $87

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

Spirit Airlines
Tue, May 6 - Tue, May 13
ORD
O'Hare Intl.
TPA
Tampa Intl.
$87 Roundtrip, found 1 hour ago
$87
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, May 6 from O'Hare Intl. to Tampa Intl., returning Tue, May 13, priced at $87 found 1 hour ago
Frontier Airlines
Mon, May 12 - Sat, May 17
ORD
O'Hare Intl.
TPA
Tampa Intl.
$90 Roundtrip, found 1 day ago
$90
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, May 12 from O'Hare Intl. to Tampa Intl., returning Sat, May 17, priced at $90 found 1 day ago
Spirit Airlines
Mon, May 19 - Thu, May 22
IAH
George Bush Intercontinental
TPA
Tampa Intl.
$92 Roundtrip, found 19 hours ago
$92
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Mon, May 19 from George Bush Intercontinental to Tampa Intl., returning Thu, May 22, priced at $92 found 19 hours ago
Spirit Airlines
Tue, May 6 - Tue, May 13
ORD
O'Hare Intl.
TPA
Tampa Intl.
$94 Roundtrip, found 1 hour ago
$94
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, May 6 from O'Hare Intl. to Tampa Intl., returning Tue, May 13, priced at $94 found 1 hour ago
Spirit Airlines
Tue, May 6 - Tue, May 13
ORD
O'Hare Intl.
TPA
Tampa Intl.
$97 Roundtrip, found 1 hour ago
$97
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, May 6 from O'Hare Intl. to Tampa Intl., returning Tue, May 13, priced at $97 found 1 hour ago
Spirit Airlines
Thu, Sep 4 - Thu, Sep 11
SAT
San Antonio Intl.
TPA
Tampa Intl.
$98 Roundtrip, found 4 days ago
$98
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, Sep 4 from San Antonio Intl. to Tampa Intl., returning Thu, Sep 11, priced at $98 found 4 days ago
Spirit Airlines
Sun, May 11 - Tue, May 13
SAT
San Antonio Intl.
TPA
Tampa Intl.
$99 Roundtrip, found 6 days ago
$99
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Sun, May 11 from San Antonio Intl. to Tampa Intl., returning Tue, May 13, priced at $99 found 6 days ago
Spirit Airlines
Fri, May 30 - Mon, Jun 2
IAH
George Bush Intercontinental
TPA
Tampa Intl.
$103 Roundtrip, found 1 day ago
$103
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, May 30 from George Bush Intercontinental to Tampa Intl., returning Mon, Jun 2, priced at $103 found 1 day ago
Frontier Airlines
Mon, May 26 - Mon, Jun 2
IAH
George Bush Intercontinental
TPA
Tampa Intl.
$103 Roundtrip, found 1 day ago
$103
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, May 26 from George Bush Intercontinental to Tampa Intl., returning Mon, Jun 2, priced at $103 found 1 day ago
Frontier Airlines
Sat, May 3 - Thu, May 8
IAH
George Bush Intercontinental
TPA
Tampa Intl.
$103 Roundtrip, found 3 days ago
$103
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, May 3 from George Bush Intercontinental to Tampa Intl., returning Thu, May 8, priced at $103 found 3 days ago
Spirit Airlines
Mon, May 19 - Fri, May 23
IAH
George Bush Intercontinental
TPA
Tampa Intl.
$104 Roundtrip, found 19 hours ago
$104
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Mon, May 19 from George Bush Intercontinental to Tampa Intl., returning Fri, May 23, priced at $104 found 19 hours ago
Frontier Airlines
Mon, May 12 - Sat, May 17
ORD
O'Hare Intl.
TPA
Tampa Intl.
$106 Roundtrip, found 1 day ago
$106
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, May 12 from O'Hare Intl. to Tampa Intl., returning Sat, May 17, priced at $106 found 1 day ago
American Airlines
Sat, May 17 - Sat, May 17
DCA
Ronald Reagan Washington National
TPA
Tampa Intl.
$172 Roundtrip, found 3 hours ago
$172
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Sat, May 17 from Ronald Reagan Washington National to Tampa Intl., returning Sat, May 17, priced at $172 found 3 hours ago
United
Sat, May 3 - Tue, May 6
IAH
George Bush Intercontinental
TPA
Tampa Intl.
$173 Roundtrip, found 3 days ago
$173
Roundtrip
found 3 days ago
Select United flight, departing Sat, May 3 from George Bush Intercontinental to Tampa Intl., returning Tue, May 6, priced at $173 found 3 days ago
Delta
Tue, May 13 - Sun, May 18
ORD
O'Hare Intl.
TPA
Tampa Intl.
$181 Roundtrip, found 5 days ago
$181
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, May 13 from O'Hare Intl. to Tampa Intl., returning Sun, May 18, priced at $181 found 5 days ago
JetBlue Airways
Fri, May 2 - Tue, May 13
ORD
O'Hare Intl.
TPA
Tampa Intl.
$217 Roundtrip, found 6 days ago
$217
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Fri, May 2 from O'Hare Intl. to Tampa Intl., returning Tue, May 13, priced at $217 found 6 days 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 May, 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 $87, 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 $87 right now, why wait?

Winter Haven Flight Information
Destination airport
Tampa Intl.
Destination airport IATA code
TPA
Roundtrip price
$87

Last Minute Hotel Deals in Winter Haven

Best Western Plus Winter Haven Inn & Suites 
Best Western Plus Winter Haven Inn & Suites 
3.5 out of 5
5801 Roosevelt Dr, Winter Haven, FL
The price is $153 per night from May 4 to May 5
$153
includes taxes & fees
May 4 - May 5
Stay at this 3.5-star business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (772 reviews)
"Nice and quiet. Professional staffs."

Reviewed on Apr 7, 2025

Best Western Plus Winter Haven Inn & Suites 
Howard Johnson by Wyndham Winter Haven FL
Howard Johnson by Wyndham Winter Haven FL
2 out of 5
1300 3rd St, SW, Winter Haven, FL
The price is $114 per night from Apr 17 to Apr 18
$114
includes taxes & fees
Apr 17 - Apr 18
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. ...
6.8/10 (1,002 reviews)
"The rooms are very clean, nice rooms. Bed are ok,"

Reviewed on Apr 6, 2025

Howard Johnson by Wyndham Winter Haven FL
Home2 Suites By Hilton Winter Haven
Home2 Suites By Hilton Winter Haven
3 out of 5
6015 Cypress Gardens Blvd, Winter Haven, FL
The price is $142 per night from May 4 to May 5
$142
includes taxes & fees
May 4 - May 5
Stay at this 3-star business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Chain ...
9/10 Wonderful! (74 reviews)
"Good size rooms and very clean. Nice front desk!"

Reviewed on Apr 14, 2025

Home2 Suites By Hilton Winter Haven
The Grove Resort & Water Park Orlando
The Grove Resort & Water Park Orlando
4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
The price is $269 per night from Apr 27 to Apr 28
$269
includes taxes & fees
Apr 27 - Apr 28
Stay at this 4-star family-friendly resort in Winter Garden. Enjoy free WiFi, 5 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful ...
8/10 Very Good! (7,427 reviews)
"Quite and clean"

Reviewed on Apr 14, 2025

The Grove Resort & Water Park Orlando
Vacation Village at Parkway
Vacation Village at Parkway
3 out of 5
2975 Arabian Nights Blvd, Kissimmee, FL
The price is $118 per night from Apr 17 to Apr 18
$118
includes taxes & fees
Apr 17 - Apr 18
Stay at this 3-star 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 ...
8.4/10 Very Good! (1,924 reviews)
"I've been going to VV for years now. Spacious units. Always clean. Nice pool area. Convenient location. Great shuttle service. Lots of parking."

Reviewed on Apr 11, 2025

Vacation Village at Parkway
Ramada by Wyndham Kissimmee Gateway
Ramada by Wyndham Kissimmee Gateway
3 out of 5
7470 W. Irlo Bronson Memorial Hwy., Kissimmee, FL
The price is $79 per night from Apr 29 to Apr 30
$79
includes taxes & fees
Apr 29 - Apr 30
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 ...
7.8/10 Good! (4,164 reviews)
"Everything was awesome. But pool was a little dirty. We grabbed the screener and cleaned ourselves"

Reviewed on Apr 12, 2025

Ramada by Wyndham Kissimmee Gateway
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Holiday Inn Club Vacations at Orange Lake Resort by IHG
4 out of 5
8505 W Irlo Bronson Memorial Hwy, Kissimmee, FL
The price is $199 per night from May 14 to May 15
$199
includes taxes & fees
May 14 - May 15
Stay at this 4-star golf resort in Kissimmee. Enjoy free parking, 7 outdoor pools, and 8 restaurants. Our guests praise the pool and the helpful staff in our ...
8.6/10 Excellent! (1,900 reviews)
"We had a great time!"

Reviewed on Apr 13, 2025

Holiday Inn Club Vacations at Orange Lake Resort by IHG
Hilton Vacation Club Aqua Sol Orlando West
Hilton Vacation Club Aqua Sol Orlando West
4 out of 5
17777 Bali Blvd, Winter Garden, FL
The price is $148 per night from Apr 22 to Apr 23
$148
includes taxes & fees
Apr 22 - Apr 23
Stay at this 4-star family-friendly hotel in Winter Garden. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff ...
8.8/10 Excellent! (3,726 reviews)
"We have stayed here a few times and we enjoy it! Perfect waterpark and pools for our 6 year old. We will be back!"

Reviewed on Apr 14, 2025

Hilton Vacation Club Aqua Sol Orlando West
See all 37,803 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.