Cheap flights from Winter Haven from $29

When you book your flight with Orbitz, find fares as low as $43 to Chicago. Flight prices vary depending on what time of year and days of the week you fly. For one-way trips, typically the cheapest month to fly is in February, while January is typically the least expensive time to fly round-trip. To make sure you get the best deal, set your target price, destination, and travel dates, and we'll send you an alert if we find cheap flights from Winter Haven that meet or beat your target price.

Orbitz gives you all the tools you need to sort through the top deals and compare available offers, including multiple filters for airlines, flight times, cancellation policies, and a flexible date calendar. Just plug in your arrival city and dates in the search fields, then filter the results by number of stops, airlines, departure times, and price. Compare flights by airline, as well as by direct flights from Winter Haven, indirect flights, dates, and times.

When you need to book a quick weekend getaway or a last-minute business trip, Orbitz has deals on last-minute flights from Winter Haven. Whether you’d like to book a plane ticket today or one week from now, the more flexible your dates are, the more likely you’ll find a deal that fits your budget. Try searching for multiple departure and arrival dates to find the best offers.

Booking your domestic or international flight from Winter Haven with Orbitz will save you money, keeping more cash in your pocket for exploring your destination. Search our vast inventory of airline providers, airports, and prices that fit all budgets. Once you book a flight, you’ll get real-time updates — either by phone, email, or text — about gate or flight changes and other important alerts. Earn rewards every time you book your travel and get credited miles and points on every Orbitz flight if you’re a member of that airline’s frequent flier program. Sounds like a win–win to us!

We at Orbitz understand that plans change, so we offer flexible bookings and cancellations on flights from Winter Haven airport. Filter the search results by flexible change policies to make sure that you can change your flight if something comes up. Cancellations are typically allowed within 24 hours of booking your flight; check your flight’s rules and restrictions before you book. For further questions or assistance, visit our customer service portal.