$34 Cheap flight deals from Chicago (CHI) to Winter Haven (TPA)
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This Weekend's Flight Deals from Chicago to Winter Haven
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $34 One Way, $58 Round Trip from Chicago to Winter Haven
Prices starting at $58 for return flights and $34 for one-way flights to Winter Haven were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Winter Haven economy flight packages
ChartHouse Clearwater Beach Marina Hotel
Apr 3 - Apr 8
Chicago (CHI) to Tampa (TPA)
Reviewed on Oct 24, 2025
Kompose Boutique Hotel
Mar 15 - Mar 19
Chicago (CHI) to Tampa (TPA)
Reviewed on Dec 15, 2025
More About Flying To Winter Haven from Chicago
Route Information for Flights from Chicago to Winter Haven
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | TPA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Winter Haven
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We do not only get the best bargains on flights from Chicago to Winter Haven, but we can tell you what to do once you get there. Whether it is a music festival, hotel recommendation or list of local attractions, Orbitz can help make your travel plan more exciting.
Combine Car Rental With Your Discount Flight For Even More Savings
Not only can we get bargain deals on flights from Chicago to Winter Haven but we can book your transport as well. By combining car rental with Chicago to Winter Haven flights, you can be sure to save money and start moving as soon as you hit the ground.
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.