Cheap Flights from Kissimmee (ISM) to Winter Haven (GIF)

Popular airlines from Kissimmee, FL (ISM-Kissimmee Gateway) to Winter Haven, FL (GIF-Winter Haven Municipal)

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Frequently asked questions

How much does a flight from Kissimmee Gateway Airport (ISM) to Winter Haven, FL (GIF-Winter Haven Municipal) cost?
Snag a cheap one-way flight or cheap return flight from Kissimmee Gateway Airport (ISM) to Winter Haven, FL (GIF-Winter Haven Municipal) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Kissimmee Gateway Airport (ISM) to Winter Haven, FL (GIF-Winter Haven Municipal)?
is the cheapest month to fly from ISM to GIF. Planning your trip for the off-season is often the key to finding better deals on flights.
What is the cheapest airline that flies from Kissimmee Gateway Airport (ISM) to Winter Haven, FL (GIF-Winter Haven Municipal)?
To find the cheapest airline that'll fly you from ISM to GIF, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Kissimmee Gateway Airport (ISM) to Winter Haven, FL (GIF-Winter Haven Municipal)?
You'll have to book a flight with a layover if you're traveling from Kissimmee Gateway Airport (ISM) to Winter Haven, FL (GIF-Winter Haven Municipal). There are no daily direct flights on this route. However, just filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from ISM to GIF?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Kissimmee Gateway Airport (ISM) to Winter Haven, FL (GIF-Winter Haven Municipal)?
To reach Winter Haven, FL (GIF-Winter Haven Municipal) on schedule, select a flight that leaves from Kissimmee Gateway Airport (ISM) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Kissimmee Gateway Airport (ISM) to Winter Haven, FL (GIF-Winter Haven Municipal) last-minute?
Last-minute bookings from ISM to GIF are usually more expensive. For the lowest prices, start looking for flights as early as possible. That being said, if your travel plans are flexible, you may land a cheap ticket right before your trip.
Is it cheaper to book an ISM to GIF flight and hotel package?
Compared with arranging flights and hotels separately, booking an ISM to GIF flight and hotel package with Expedia could result in significant savings. Better yet, managing everything in one place will take the stress out of travel planning. Just pick your flights and choose from our wide range of hotels, then tailor your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Kissimmee Gateway Airport (ISM) to Winter Haven, FL (GIF-Winter Haven Municipal)?
In most instances, you're able to cancel or reschedule your ISM to GIF flight. However, there may be additional charges, especially if you made your booking more than 24 hours ago. Check your itinerary for the airline's rules and fees on flight changes, or if you need more details, visit our Customer Service portal.

Travel information

Origin airport
Kissimmee Gateway
Destination airport
Winter Haven Municipal
Distance
25 mi

Book with confidence

Kissimmee to Winter Haven Flights

The cheapest times to fly from Kissimmee to Winter Haven

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Kissimmee to Winter Haven are during the month of . You can find some of the cheapest flights from Kissimmee to Winter Haven with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Kissimmee to Winter Haven

Sunday is one of the best days to book for cheap flights from Kissimmee to Winter Haven: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Kissimmee to Winter Haven

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Kissimmee to Winter Haven in 2026. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Kissimmee to Winter Haven flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Kissimmee to Winter Haven airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Kissimmee to Winter Haven Flights

Explore a world of travel with Expedia

*Available to One Key members.