Cheap Flights to Winter Haven from $30
Wander Wisely with exceptional service, 24/7 supportOpens in a new window
Feel at ease with free flight cancellations within 24 hours of booking
Change your flight without a fee on select flights
How Much Does it Cost To Fly To Winter Haven?
The cheapest prices found with in the last 7 days for return flights were $58 and $30 for one-way flights to Winter Haven for the period specified. Prices and availability are subject to change. Additional terms apply
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$58 Roundtrip, found 3 hours ago
$58
Roundtrip
found 3 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| PHL | Tampa | January 25 to January 29 | $59 |
| ORD | Tampa | January 31 to February 5 | $61 |
| ORD | Tampa | January 31 to February 5 | $61 |
| CLE | Tampa | February 18 to February 25 | $68 |
| DTW | Tampa | February 8 to February 10 | $69 |
| BOS | Tampa | January 24 to January 28 | $87 |
| LGA | Tampa | January 31 to February 7 | $87 |
| MSP | Tampa | January 31 to February 7 | $130 |
| EWR | Tampa | March 3 to March 7 | $137 |
| YYZ | Tampa | April 8 to April 13 | $154 |
| MSP | St. Petersburg - Clearwater | April 5 to April 9 | $167 |
| ORD | St. Petersburg - Clearwater | March 8 to March 14 | $1,396 |
| ORD | St. Petersburg - Clearwater | March 8 to March 14 | $1,396 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| CLE | Tampa | January 18 to January 23 | $94 |
| LGA | Tampa | January 18 to January 28 | $125 |
| PHL | Tampa | January 18 to January 24 | $132 |
| DTW | Tampa | January 17 to January 18 | $146 |
| EWR | Tampa | January 17 to January 24 | $159 |
| ORD | Tampa | January 17 to January 22 | $192 |
| ORD | Tampa | January 17 to January 22 | $192 |
| BOS | Tampa | January 18 to January 23 | $207 |
| YYZ | Tampa | January 18 to January 26 | $221 |
| MSP | Tampa | January 18 to January 21 | $304 |
Winter Haven Flight Information
Traveling to | Winter Haven |
|---|---|
Lowest Price | $58 |
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
$85 nightly
The price is $95 total per night from Jan 12 to Jan 13
$95 total
Jan 12 - Jan 13
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. ...
7/10 Good! (1,009 reviews)
Good
Reviewed on Jan 5, 2026
Budget Inn Winter Haven
401 6th Street HWY 17N Winter Haven FL
$83 nightly
The price is $93 total per night from Jan 13 to Jan 14
$93 total
Jan 13 - Jan 14
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 ...
6.6/10 (273 reviews)
Good
Reviewed on Dec 21, 2025
Rodeway Inn & Suites Winter Haven Chain Of Lakes
1911 Cypress Gardens Blvd Winter Haven FL
$95 nightly
The price is $106 total per night from Jan 11 to Jan 12
$106 total
Jan 11 - Jan 12
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 Peppa ...
5.2/10 (254 reviews)
Great night
Reviewed on Nov 27, 2025
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 ...
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
$85 nightly
The price is $95 total per night from Jan 12 to Jan 13
$95 total
Jan 12 - Jan 13
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. ...
7/10 Good! (1,009 reviews)
Good
Reviewed on Jan 5, 2026
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$100 nightly
The price is $113 total per night from Jan 13 to Jan 14
$113 total
Jan 13 - Jan 14
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 ...
6.8/10 (994 reviews)
Everything was good. Not sure what the message from the hotel was about having a pet. We didn't have a pet with us and no one said anything to us when we checked out.
Reviewed on Jan 3, 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
$85 nightly
The price is $95 total per night from Jan 12 to Jan 13
$95 total
Jan 12 - Jan 13
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. ...
7/10 Good! (1,009 reviews)
Good
Reviewed on Jan 5, 2026
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$100 nightly
The price is $113 total per night from Jan 13 to Jan 14
$113 total
Jan 13 - Jan 14
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 ...
6.8/10 (994 reviews)
Everything was good. Not sure what the message from the hotel was about having a pet. We didn't have a pet with us and no one said anything to us when we checked out.
Reviewed on Jan 3, 2026
Hampton Inn Winter Haven
202 Cypress Gardens Blvd Winter Haven FL
$130 nightly
The price is $146 total per night from Jan 18 to Jan 19
$146 total
Jan 18 - Jan 19
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 ...
8.8/10 Excellent! (1,000 reviews)
Clean hotel with a good breakfast. Staff was very friendly!!
Reviewed on Jan 2, 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
$95 nightly
The price is $106 total per night from Jan 11 to Jan 12
$106 total
Jan 11 - Jan 12
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 Peppa ...
5.2/10 (254 reviews)
Great night
Reviewed on Nov 27, 2025
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.
Don't see what you're looking for?
See all available trips from Chicago to Winter Haven
View all tripsWinter Haven flight + hotel packages - first class flights
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Midsize
Tampa, Florida, USA
$1
$2 total
found 3 days ago
Special
Tampa, Florida, USA
$1
$2 total
found 3 days ago
Compact
Tampa, Florida, USA
$1
$2 total
found 3 days ago
Economy
Tampa, Florida, USA
$1
$2 total
found 3 days ago
Lowest prices found within the past 3 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
Find the perfect hotel after your flight
Winter Haven Vacation Rentals
Great Deals on alternative accommodations
Winter Haven Car Rentals
Affordable cars to get you around town
Winter Haven Vacations
Save more by combining flights, hotels and cars
Things to do in Winter Haven
Activities, attractions and tours
Explore More Ways to Travel with Travelocity
- Orlando Hotels
- B&B in Eloise
- Cabins in Eloise
- Condos in Eloise
- Eloise Hotels
- Motels in Eloise
- Hotels near Inman Park
- Hotels near LEGOLAND® Florida
- Hotels near Indigo's Billiards
- Hotels near Rotary Park
- Motels in Winter Haven Station
- Hotels near Northgate Shopping Center
- Hotels near Theatre Winter Haven
- Hotels near Chain Of Wakes
- Holiday Park Resorts in Cypress Gardens
- Cheap Hotels in Cypress Gardens
- Pet Friendly Hotels in Cypress Gardens
- Lodges in Cypress Gardens
- Motels in Cypress Gardens
- Resorts in Cypress Gardens
- Hotels near Baytree Golf Club
- Hotels near Winter Haven Municipal
- Hotels near Sertoma Park
- Jan Phyl Village Hotels
- Cabins in Auburndale
- Condos in Auburndale
- Cottages in Auburndale
- Extended Stay Hotels in Auburndale
- Guest Houses in Auburndale
- Hostels in Auburndale
- Cheap Hotels in Auburndale
- Pet Friendly Hotels in Auburndale
- Auburndale Hotels
- Houseboats in Auburndale
- Motels in Auburndale
- Vacation Homes in Auburndale
- Villas in Auburndale
- 5 Star Hotels in Eagle Lake
- Apartments in Eagle Lake
- B&B in Eagle Lake
- Cabins in Eagle Lake
- Condos in Eagle Lake
- Cottages in Eagle Lake
- Eagle Lake Hotels
- Houseboats in Eagle Lake
- Vacation Homes in Eagle Lake
- Rv Parks in Eagle Lake
- Resorts in Eagle Lake
- Hotels near Willowbrook Golf Course
- Flights to Orlando
- Flights to Tampa
- Flights to Celebration
- Flights to Lithia
- Flights to Lakeland - Winter Haven
- Flights to Lakeland
- Flights to Crystal Springs
- Flights to Avon Park
- Flights to Zephyrhills
- Flights to Lake Buena Vista
- Flights to Haines City
- Flights to Lake Wales
- Flights to Dover
- Flights to Waverly
- Flights to Valrico
- Flights to Fort Meade
- Flights to Lake Alfred
- Flights to Frostproof
- Flights to Kissimmee
- Flights from Winter Haven Municipal
- Flights to Lake Buena Vista North
- Flights to Plant City
- Flights to Champions Gate
- Flights to Four Corners
- Flights to Poinciana
- Flights to Florida
- Flights to Central Florida
- Flights to Bartow
- Flights to Auburndale
- Flights to Davenport