Cheap Flight Deals to Winter Haven FL from CA $40
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How to find cheap flights to Winter Haven?
The cheapest prices found with in the last 7 days for return flights were CA $80 and CA $40 for one-way flights to Winter Haven for the period specified. Prices and availability are subject to change. Additional terms apply
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| DTW | Tampa | January 21 to January 23 | CA $91 |
| ORD | Tampa | February 1 to February 7 | CA $139 |
| LGA | Tampa | February 21 to February 25 | CA $139 |
| ORD | Tampa | February 1 to February 7 | CA $139 |
| PHL | Tampa | January 12 to January 15 | CA $153 |
| EWR | Tampa | February 21 to February 25 | CA $178 |
| BOS | Tampa | January 15 to January 22 | CA $187 |
| YYZ | Tampa | February 9 to February 16 | CA $251 |
| CLE | Tampa | January 2 to January 7 | CA $272 |
| MSP | Tampa | March 9 to March 19 | CA $366 |
| MSP | St. Petersburg - Clearwater | March 9 to March 19 | CA $489 |
Your guide to flights to Winter Haven, FL
Spirit Airlines, Porter Airlines fly to Winter Haven, so use Travelocity to search, find, and compare some truly tempting deals from the 4 airlines—that way you can be sure you’ve found the best deal for you. A flight to Winter Haven FL currently costs between CA $80 and CA $489. Prices vary, but for the best fares, travel in January when prices are at their lowest.
Top tips for finding cheap flights to Winter Haven
The cheapest flight for a round trip to Winter Haven is currently CA $80. When you search for flights to Winter Haven, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Winter Haven for nearby days. The cheapest month to travel to Winter Haven is January from our list of deals available.
But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.
How to cancel flights to Winter Haven
We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.
Why you should book your flight to Winter Haven with Travelocity
We have top deals on plane tickets even for last minute flights to Winter Haven, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Winter Haven for less.
Find The Perfect Hotel For After Your Flight
Amazing Place to Stay After Flight to Winter Haven
Howard Johnson by Wyndham Winter Haven FL
A very curious staff! Which was very nice! We had a good time! The hotel was nice!Will definitely use them again!
Reviewed on Dec 14, 2025
Budget Inn Winter Haven
Good
Reviewed on Dec 21, 2025
Rodeway Inn & Suites Winter Haven Chain Of Lakes
Great night
Reviewed on Nov 27, 2025
Winter Haven Gardens Inn
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
Luxury Hotels in Winter Haven
Howard Johnson by Wyndham Winter Haven FL
A very curious staff! Which was very nice! We had a good time! The hotel was nice!Will definitely use them again!
Reviewed on Dec 14, 2025
Lake Roy Beach Inn
The property is perfect if you are looking for an alternative to the high prices of Legoland hotels that are nearby. It is very outdated but has a lovely view of lake. We did not use the pool while it looked quite clean.
Reviewed on Dec 15, 2025
Family Friendly Hotels in Winter Haven
Howard Johnson by Wyndham Winter Haven FL
A very curious staff! Which was very nice! We had a good time! The hotel was nice!Will definitely use them again!
Reviewed on Dec 14, 2025
Lake Roy Beach Inn
The property is perfect if you are looking for an alternative to the high prices of Legoland hotels that are nearby. It is very outdated but has a lovely view of lake. We did not use the pool while it looked quite clean.
Reviewed on Dec 15, 2025
Hampton Inn Winter Haven
Had a wonderful stay! The room was clean, the bed was incredibly comfortable, and the staff were welcoming from the moment I arrived. Perfect location for exploring the area. I’d definitely stay here again!"
Reviewed on Dec 22, 2025
Rodeway Inn & Suites Winter Haven Chain Of Lakes
Great night
Reviewed on Nov 27, 2025
Best Winter Haven Flight and Hotel Packages
Winter Haven flight + hotel packages - economy flights
Winter Haven flight + hotel packages - business class flights
Winter Haven flight + hotel packages - first class flights
Need a car after flight to Winter Haven?
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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.