$80 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 $80 One Way, $163 Round Trip from Chicago to Winter Haven
Prices starting at $163 for return flights and $80 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
Pelican Pointe Clearwater Beach Hotel
Jun 20 - Jun 27
Chicago (CHI) to Tampa (TPA)
Reviewed on Nov 26, 2025
Cedar Cove Resort and Cottages
Jun 26 - Jun 30
Chicago (ORD) to Tampa (TPA)
Tampa (TPA) to Chicago (ORD)
Reviewed on Aug 10, 2025
Plaza Beach Hotel Beachfront Resort
Jun 16 - Jun 24
Chicago (ORD) to Tampa (TPA)
Tampa (TPA) to Chicago (ORD)
Reviewed on Jul 21, 2024
Winter Haven packages with premium economy flights
Captiva Beach Resort
Jun 12 - Jun 19
Chicago (ORD) to Tampa (TPA)
Tampa (TPA) to Chicago (ORD)
Reviewed on Jan 11, 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club
Jun 12 - Jun 19
Chicago (ORD) to Tampa (TPA)
Tampa (TPA) to Chicago (ORD)
Reviewed on May 7, 2026
Legacy Hotel at IMG Academy
Jun 12 - Jun 19
Chicago (ORD) to Tampa (TPA)
Tampa (TPA) to Chicago (ORD)
Reviewed on Aug 14, 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
When you’re ready to take your next trip, get the most affordable prices on flights from Chicago to Winter Haven with Orbitz! The guaranteed low prices and cutting-edge mobile tools on Orbits make it easy for you to plan your next great vacation.
Keep Up With Sudden Flight Changes
As any traveler knows, air travel can suddenly be temporarily halted due to service disruptions. Along with offering the best fares for flights from Chicago to Winter Haven, Orbitz also offers free mobile phone and email alerts that help you keep up with sudden changes to your flight plans. Choose from email, text, or voice message alerts.
Get Great Prices for Chicago to Winter Haven Flights
Orbitz features both an Android app and an iPhone app to give you the lowest prices for Chicago to Winter Haven flights. Use these mobile apps to get updates on your flight, the details of your itinerary, and to learn about available hotel deals in the area.
Fly for Less and Earn Miles
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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.