Search Cheap Flights to
Highland Park

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Highland Park Flights as Low as $148

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

Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Sun Country Airlines
Delta
American Airlines
Bargain Flight
Alaska Airlines
JetBlue Airways
Sun Country Airlines
Sun Country Airlines
Sun Country Airlines

Cheap Flights to Highland Park

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

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

Frequently Asked Questions About flights to Highland Park

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Highland Park 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 Highland Park?

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 Highland Park are in February, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Highland Park?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Highland Park.

What airport is best to fly into Highland Park?

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

How much are flights to Highland Park?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Highland Park on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $148, 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 Highland Park?

The trick to saving a stack of cash on your flight to Highland Park? 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 $148 right now, why wait?

Highland Park Flight Information
Destination airport
Tampa Intl.
Destination airport IATA code
TPA
Roundtrip price
$55

Last Minute Hotel Deals in Highland Park

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
200 Cypress Gardens Boulevard Winter Haven FL
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,003 reviews)
Yes they were

Reviewed on Jan 18, 2026

Holiday Inn Winter Haven by IHG
Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG

2.5 out of 5
2953 Ridge Way Lake Wales FL
Book a stay at this business-friendly hotel in Lake Wales. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,003 reviews)
Clean

Reviewed on Jan 20, 2026

Holiday Inn Express Lake Wales N-Winter Haven by IHG
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. ...
7/10 Good! (1,005 reviews)
Excellent service and location. Quiet and clean.

Reviewed on Jan 20, 2026

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! (62 reviews)
loved the hotel and all the Lego extras maybe update the landscape.

Reviewed on Jan 12, 2026

Legoland Florida Hotel
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
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 ...
9.4/10 Exceptional! (1,131 reviews)
I had a wonderful stay at this hotel. It was very spacious, extremely clean, and felt comfortable and welcoming throughout my visit.

Reviewed on Jan 20, 2026

Best Western Plus Winter Haven Inn & Suites 
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! (153 reviews)
Everything was great!

Reviewed on Jan 21, 2026

LEGOLAND Beach Retreat
Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven

3 out of 5
6015 Cypress Gardens Blvd Winter Haven FL
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Peppa ...
9.4/10 Exceptional! (291 reviews)
First note- Samantha at check in is the best person I’ve met for check in! Very informative and knowledgeable of the area! Rooms are beautiful, spacious & very very clean. Well taken care of property and always see the staff cleaning inside and outside especially in the morning time. Perfect hotel, ...

Reviewed on Jan 19, 2026

Home2 Suites By Hilton Winter Haven
Hampton Inn Winter Haven

Hampton Inn Winter Haven

2.5 out of 5
202 Cypress Gardens Blvd Winter Haven FL
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! (1,007 reviews)
Room was clean, but cold…Air was still on.,however the Temperature dropped outside! Staff were friendly and professional. The deadbolt lock was loose on door and sadly, the bathroom smelled like smoke and the shower water took exceptionally long to get warm! Otherwise it was a good stay!

Reviewed on Jan 22, 2026

Hampton Inn 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.