
$45 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 $45 One Way, $88 Round Trip from Chicago to Winter Haven
Prices starting at $88 for return flights and $45 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

voco Sarasota by IHG
Aug 29 - Sep 2
Chicago (CHI) to Tampa (TPA)
Tampa (TPA) to Chicago (CHI)
Reviewed on Jun 30, 2024

Ocean Club Treasure Island Hotel
Sep 15 - Sep 19
Chicago (CHI) to Tampa (TPA)
Tampa (TPA) to Chicago (CHI)
Reviewed on Apr 29, 2025

The Avalon Club
Aug 29 - Sep 1
Chicago (CHI) to Tampa (TPA)
Reviewed on Jun 7, 2024
Winter Haven first class flight packages

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG
Sep 13 - Sep 17
Chicago (ORD) to Tampa (TPA)
Tampa (TPA) to Chicago (ORD)
Reviewed on Jul 13, 2025

TownePlace Suites Tampa Casino Area
Sep 13 - Sep 17
Chicago (ORD) to Tampa (TPA)
Tampa (TPA) to Chicago (ORD)
Reviewed on Jun 9, 2025

Fairfield Inn & Suites by Marriott Tampa Riverview
Sep 13 - Sep 17
Chicago (ORD) to Tampa (TPA)
Tampa (TPA) to Chicago (ORD)
Reviewed on Sep 15, 2023
More About Flying To Winter Haven from Chicago
Route Information for Flights from Chicago to Winter Haven
Origin Airport IATA Code | CHI |
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Destination Airport IATA Code | TPA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Winter Haven
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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.