
$29 Cheap flight deals from Chicago (CHI) to Clearwater (TPA)
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This Weekend's Flight Deals from Chicago to Clearwater
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 $29 One Way, $59 Round Trip from Chicago to Clearwater
Prices starting at $59 for return flights and $29 for one-way flights to Clearwater were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Clearwater economy flight packages


Holiday Inn Express Lake Wales N-Winter Haven by IHG
Feb 4 - Feb 8
Chicago (CHI) to Tampa (TPA)
Reviewed on Jul 18, 2023

Plaza Beach Hotel Beachfront Resort
Jan 24 - Jan 31
Chicago (CHI) to Tampa (TPA)
Reviewed on Jul 21, 2024
Clearwater packages with premium economy flights

Hilton Clearwater Beach Resort & Spa
Feb 1 - Feb 5
Chicago (CHI) to Tampa (TPA)
Reviewed on Dec 21, 2025

Innisbrook Resort
Feb 1 - Feb 5
Chicago (CHI) to Tampa (TPA)
Reviewed on Aug 9, 2025

More About Flying To Clearwater from Chicago
Route Information for Flights from Chicago to Clearwater
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | TPA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Clearwater
Orbitz has your discount air ticket deals for flights from Chicago to Clearwater. The guaranteed low prices from flights and hotels to car rentals and vacation packages make Orbitz the perfect travel website for budget trip planning.
Use Orbitz to Earn Frequent Flyer Miles
You know you can find great fares with Orbitz—but did you know you don’t have to give up earning miles or points towards your frequent flyer program? If you’re a member of a frequent flyer program, you can use Orbitz to find bargain prices for flights from Chicago to Clearwater and still earn points or miles. All you have to do is add your frequent flyer account number as you book your tickets online. After you complete your travel plans, you can choose to keep your account number in your personal account profile so that you can automatically add it to your next Orbitz reservation.
Orbitz Keeps You Up-to-Date With Instant Flight Alerts
While Orbitz gives you access to cheap tickets for Chicago to Clearwater flights, the travel site also offers free email, voice, or text message alerts to keep you informed of any abrupt changes or delays that affect your travel. You can even choose to have the alerts sent to up to six of your mobile or email contacts to keep your friends in the loop.
Bargain Chicago to Clearwater Flights With Mobile Apps
Download the cutting-edge Orbitz app for either Android or iPhone, and use it to check on the status of your upcoming flights from Chicago to Clearwater at any time. These apps also make it easy for you to book discount hotel rates in your destination city and check for deals on future Chicago to Clearwater flights.
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- Visit Sand Key Park
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- Beach Hotels in Clearwater Beach
- Hotels near Sand Key Park
- Hotels in Clearwater Beach
- Car rentals at Tampa Airport (TPA)
- Condos in Clearwater Beach
- Flights to Tampa
- Hotel Wedding Venues in Clearwater Beach
- Flights to Clearwater Beach
- Hotels near Pier 60 Park
- Family Hotels in Clearwater Beach
- Cheap Hotels in Clearwater Beach
- Pet-friendly Hotels in Clearwater Beach
- Cottages in Clearwater Beach
- Motels in Clearwater Beach
- Oceanfront Hotels in Clearwater Beach
- Visit Beach Walk
- Clearwater Beach vacation rentals
- Clearwater Beach vacations
- Visit Sand Key Park
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.



