Cheap Flights to Winter Haven from $52
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How Much Does it Cost To Fly To Winter Haven?
The cheapest prices found with in the last 7 days for return flights were $61 and $52 for one-way flights to Winter Haven for the period specified. Prices and availability are subject to change. Additional terms apply
CVG
Cincinnati - Northern Kentucky Intl.
TPA
Tampa Intl.
$61 Roundtrip, found 2 days ago
$61
Roundtrip
found 2 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| PHL | Tampa | December 6 to December 15 | $74 |
| CLE | Tampa | October 24 to October 31 | $78 |
| PHL | St. Petersburg - Clearwater | October 2 to October 5 | $78 |
| DTW | Tampa | December 2 to December 6 | $102 |
| ORD | Tampa | December 4 to December 6 | $144 |
| ORD | Tampa | December 4 to December 6 | $144 |
| RFD | St. Petersburg - Clearwater | October 30 to November 2 | $151 |
| SWF | Tampa | September 30 to October 3 | $153 |
| MSP | Tampa | November 14 to November 18 | $161 |
| DTW | Lakeland | December 7 to December 14 | $164 |
| SWF | St. Petersburg - Clearwater | December 3 to December 6 | $164 |
| YYZ | Tampa | November 22 to November 30 | $179 |
| BOS | Tampa | November 3 to November 7 | $179 |
| EWR | Tampa | October 27 to November 3 | $249 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| SWF | Tampa | September 19 to September 26 | $246 |
| SWF | St. Petersburg - Clearwater | September 20 to September 27 | $264 |
| YYZ | Tampa | September 19 to November 22 | $279 |
| PHL | Tampa | September 20 to October 4 | $280 |
| MDW | Tampa | September 19 to September 26 | $328 |
| EWR | Tampa | September 19 to September 22 | $357 |
| CLE | Tampa | September 20 to September 23 | $364 |
| ORD | Tampa | September 18 to September 20 | $385 |
| DTW | Tampa | September 18 to September 20 | $385 |
| RFD | St. Petersburg - Clearwater | September 18 to September 21 | $395 |
| MSP | Tampa | September 19 to September 22 | $420 |
| BOS | Tampa | September 19 to September 23 | $536 |
Winter Haven Flight Information
Traveling to | Winter Haven |
|---|---|
Lowest Price | $61 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing Winter Haven Accommodation Deals
Howard Johnson by Wyndham Winter Haven FL
1300 3rd St Winter Haven FL
$77 nightly
The price is $86 total per night from Sep 18 to Sep 19
$86 total
Sep 18 - Sep 19
Total with taxes and fees
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. ...
Budget Inn Winter Haven
401 6th Street HWY 17N Winter Haven FL
$81 nightly
The price is $90 total per night from Oct 12 to Oct 13
$90 total
Oct 12 - Oct 13
Total with taxes and fees
Stay at this motel in Winter Haven. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Winter Haven Public Library ...
Rodeway Inn & Suites Winter Haven Chain Of Lakes
1911 Cypress Gardens Blvd Winter Haven FL
$81 nightly
The price is $90 total per night from Sep 16 to Sep 17
$90 total
Sep 16 - Sep 17
Total with taxes and fees
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Lake ...
5.4/10 (289 reviews)
"Ok yo stay one night, the receptionist veo helpful and friendly. No breakfast offered, even we paid for"
Reviewed on Sep 7, 2026
Save an average of 15% on thousands of hotels when you're signed in
Winter Haven Gardens Inn
1150 3rd Street SW Winter Haven FL
Stay at this hotel in Winter Haven. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Indigo's Family Fun Center ...
5.8/10 (1,000 reviews)
Booked a hotel that was permanently closed
"Didn't stay. Got here and sign on door saying permanent closed. Had to find somewhere else to stay at last minute. Good thing other family members had extra room and allowed us to stay with them."
Reviewed on Dec 18, 2022
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.
Luxury Hotels in Winter Haven
Howard Johnson by Wyndham Winter Haven FL
1300 3rd St Winter Haven FL
$77 nightly
The price is $86 total per night from Sep 18 to Sep 19
$86 total
Sep 18 - Sep 19
Total with taxes and fees
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. ...
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$88 nightly
The price is $99 total per night from Sep 14 to Sep 15
$99 total
Sep 14 - Sep 15
Total with taxes and fees
Book a stay at this beach hotel in Winter Haven. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
7/10 Good! (1,000 reviews)
"My wife and her sister stayed the first night which was fine, so I booked a second night ,the breakfast are free but you have to paid a 50.00 to use the utensils nonrefundable so breakfast isn't free however please take note that you are responsible for washing the dishware that you have chosen to ..."
Reviewed on Aug 26, 2026
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.
Family Friendly Hotels in Winter Haven
Howard Johnson by Wyndham Winter Haven FL
1300 3rd St Winter Haven FL
$77 nightly
The price is $86 total per night from Sep 18 to Sep 19
$86 total
Sep 18 - Sep 19
Total with taxes and fees
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. ...
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$88 nightly
The price is $99 total per night from Sep 14 to Sep 15
$99 total
Sep 14 - Sep 15
Total with taxes and fees
Book a stay at this beach hotel in Winter Haven. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
7/10 Good! (1,000 reviews)
"My wife and her sister stayed the first night which was fine, so I booked a second night ,the breakfast are free but you have to paid a 50.00 to use the utensils nonrefundable so breakfast isn't free however please take note that you are responsible for washing the dishware that you have chosen to ..."
Reviewed on Aug 26, 2026
Hampton Inn Winter Haven
202 Cypress Gardens Blvd Winter Haven FL
$114 nightly
The price is $128 total per night from Sep 20 to Sep 21
$128 total
Sep 20 - Sep 21
Total with taxes and fees
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,002 reviews)
"I didn’t like that I couldn’t control the room temperature. The room was very hot all through out the night to the point that my mate and I were both were sweating in our sleep. I didn’t pay $155 dollars to come to a hotel room to sweat all night. The breakfast was very satisfying and delicious. ..."
Reviewed on Sep 13, 2026
Save an average of 15% on thousands of hotels when you're signed in
Rodeway Inn & Suites Winter Haven Chain Of Lakes
1911 Cypress Gardens Blvd Winter Haven FL
$81 nightly
The price is $90 total per night from Sep 16 to Sep 17
$90 total
Sep 16 - Sep 17
Total with taxes and fees
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Lake ...
5.4/10 (289 reviews)
"Ok yo stay one night, the receptionist veo helpful and friendly. No breakfast offered, even we paid for"
Reviewed on Sep 7, 2026
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.
Best Winter Haven Flight and Hotel Packages
Winter Haven flight + hotel packages - economy flights
Price found within the past 48 hours. Click for updated prices.
Winter Haven flight + hotel packages - premium economy flights
Price found within the past 48 hours. Click for updated prices.
Winter Haven flight + hotel packages - first class flights
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Chicago to Winter Haven
View all tripsNeed a Car For After Your Flight?
Standard
Tampa, USA
$5
$10 total
found 4 days ago
Midsize
Tampa, USA
$6
$11 total
found 4 days ago
Compact SUV
Tampa, USA
$7
$13 total
found 4 days ago
Economy
Tampa, USA
$7
$13 total
found 1 day ago
Lowest prices found within the past 4 days. Prices and availability subject to change. Additional terms may apply.
Flights To Winter Haven
Situated within striking range of both Orlando and Tampa, Winter Haven is a popular spot within Central Florida, as the combo of amusement parks, picturesque natural areas, excellent water skiing spots, and laid-back atmosphere make it a place where you can have fun without feeling in a rush. Hence, it's a true Florida town. If you plan on getting here via air, you're in luck too, as you can choose to land at either Orlando International Airport (MCO) or Tampa International Airport (TPA).
Transportation from TPA and MCO
If you've found some great deals for Winter Haven flights landing at Tampa International Airport, know you'll be roughly 57 miles from the city when you arrive. Thus, your best option is to rent a car in the baggage claim area, though you could catch a taxi outside the baggage claim level, or book a shuttle van. If you've discovered some good flights to Winter Haven that land at Orlando International Airport, know you'll be roughly 48 miles from the city when you arrive. Hence, your most convenient option is to also get a rental vehicle, which can be arranged on the ground transportation level of any terminal at MCO. It is possible to take a public bus from MCO to Winter Haven, but there are numerous transfers, and it's very time consuming. After all, you'll want to drop your bags off at your choice of Winter Haven hotels and go explore as quick as possible.
Experience Winter Haven
Enjoy the rides at Legoland Florida, and fish at Lake Hamilton while in Winter Haven. If you want to find discount plane tickets and hotel rooms for Winter Haven, look no further than Travelocity. We offer a price match guarantee, which means that if you find cheaper airfare to Winter Haven or lower cost packages to Winter Haven elsewhere, we'll match that price and refund the difference.
More Ways To Wander
Winter Haven Hotels
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Winter Haven Vacation Rentals
Great Deals on alternative accommodations
Winter Haven Car Rentals
Affordable cars to get you around town
Winter Haven Vacations
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Things to do in Winter Haven
Activities, attractions and tours
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