$39 Cheap flight deals from Chicago (CHI) to Clearwater Beach (TPA)

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This Weekend's Flight Deals from Chicago to Clearwater Beach

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.

Sat, Nov 30 - Fri, Dec 6
MDW
Midway Intl.
TPA
Tampa Intl.
$215 Roundtrip, found 3 days ago
$215
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Nov 30 from Midway Intl. to Tampa Intl., returning Fri, Dec 6, priced at $215 found 3 days ago
Sun, Dec 1 - Mon, Dec 9
ORD
O'Hare Intl.
TPA
Tampa Intl.
$277 Roundtrip, found 3 hours ago
$277
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sun, Dec 1 from O'Hare Intl. to Tampa Intl., returning Mon, Dec 9, priced at $277 found 3 hours ago

Airfares from $39 One Way, $88 Round Trip from Chicago to Clearwater Beach

Prices starting at $88 for return flights and $39 for one-way flights to Clearwater Beach were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Feb 5 - Fri, Feb 7
MDW
Chicago
TPA
Tampa
$88 Roundtrip, found 7 hours ago
$88
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Wed, Feb 5 from Chicago to Tampa, returning Fri, Feb 7, priced at $88 found 7 hours ago
Tue, Dec 17 - Fri, Dec 20
ORD
Chicago
TPA
Tampa
$97 Roundtrip, found 3 hours ago
$97
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Tue, Dec 17 from Chicago to Tampa, returning Fri, Dec 20, priced at $97 found 3 hours ago
Sat, Jan 18 - Sat, Jan 25
ORD
Chicago
TPA
Tampa
$157 Roundtrip, found 3 hours ago
$157
Roundtrip
found 3 hours ago
Select United flight, departing Sat, Jan 18 from Chicago to Tampa, returning Sat, Jan 25, priced at $157 found 3 hours ago
Sat, Jan 18 - Sat, Jan 25
ORD
Chicago
TPA
Tampa
$157 Roundtrip, found 3 hours ago
$157
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Sat, Jan 18 from Chicago to Tampa, returning Sat, Jan 25, priced at $157 found 3 hours ago
Mon, Jan 6 - Mon, Jan 13
ORD
Chicago
TPA
Tampa
$196 Roundtrip, found 3 hours ago
$196
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Mon, Jan 6 from Chicago to Tampa, returning Mon, Jan 13, priced at $196 found 3 hours ago

Clearwater Beach economy flight packages

Price found within the past 48 hours. Click for updated prices.
Legacy Vacation Resorts - Indian Shores
3.0-star property

Legacy Vacation Resorts - Indian Shores

9.2/10 Wonderful! (858 reviews)

Jan 16 - Jan 21

5 night stay

Chicago (CHI) to Tampa (TPA)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 5 hours ago
Mable at the office front desk was knowledgeable and helpful. We like the area; the beach has great sand, and there are a variety of restaurants with good food. We will stay there again.

Reviewed on Feb 20, 2021

Ocean Club Treasure Island Hotel
4.0-star property

Ocean Club Treasure Island Hotel

9.4/10 Exceptional! (207 reviews)

Jan 1 - Jan 5

4 night stay

Chicago (CHI) to Tampa (TPA)

Spirit Airlines • Coach

Tampa (TPA) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Great place. Clean and beautiful. Incredible views.

Reviewed on Nov 12, 2024

Home2 Suites by Hilton Tampa Downtown Channel District
3.0-star property

Home2 Suites by Hilton Tampa Downtown Channel District

9.4/10 Exceptional! (659 reviews)

Dec 30 - Jan 4

5 night stay

Chicago (CHI) to Tampa (TPA)

Frontier Airlines • Coach

Tampa (TPA) to Chicago (CHI)

Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Awesome location for the cruise terminals

Reviewed on Aug 28, 2024

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Clearwater Beach packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
4.0-star property

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

8.8/10 Excellent! (1,097 reviews)

Jan 10 - Jan 13

3 night stay

Chicago (MDW) to Tampa (TPA)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 4 hours ago
Nice property the room was the best.

Reviewed on Oct 28, 2024

Sheraton Sand Key Resort
4.0-star property

Sheraton Sand Key Resort

8.4/10 Very Good! (1,002 reviews)

Jan 10 - Jan 13

3 night stay

Chicago (MDW) to Tampa (TPA)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 4 hours ago
I have stayed here several times and have always enjoyed it. It’s a beautiful property with plenty to do and outside the traffic Clearwater. My only complaint was that this time my wife and I had checked in later in the evening and when we walked in, a huge roach was running through the room. I know it’s Florida, it happens, but after I got rid of this thing, I went into the bathroom to flush it, and another even bigger one was there, with a baby right next to it. My wife freaked. I killed it, flushed them all, looked around and after I calmed her down we had a great time.

Reviewed on Jul 27, 2024

Element Tampa Midtown
3.0-star property

Element Tampa Midtown

8.6/10 Excellent! (269 reviews)

Jan 10 - Jan 13

3 night stay

Chicago (MDW) to Tampa (TPA)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 4 hours ago
Extra towels never made it

Reviewed on Feb 13, 2024

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Clearwater Beach first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
4.0-star property

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

8.8/10 Excellent! (1,097 reviews)

Dec 27 - Dec 29

2 night stay

Chicago (MDW) to Tampa (TPA)

Delta • Non-stop roundtrip • FirstClass
per person
found 1 day ago
Nice property the room was the best.

Reviewed on Oct 28, 2024

The Barrymore Hotel Tampa Riverwalk
3.0-star property

The Barrymore Hotel Tampa Riverwalk

8/10 Very Good! (1,410 reviews)

Dec 27 - Dec 29

2 night stay

Chicago (MDW) to Tampa (TPA)

Delta • Non-stop roundtrip • FirstClass
per person
found 1 day ago
Overall, the hotel was clean & quiet. I was in town to attend an event at the Straz center across the street so the location was perfect. While I did not encounter an staff that was rude, I didn't find them to be overly helpful. I asked for the front desk staff to schedule a cab pickup for me. Based on my experiences at hotels similar to this, I thought it would be provided here as well. Wrong; "you have to call them yourself; we don't do that." Nor did they recommend a cab company to use. The restaurant in the hotel is fair at best. Staffed with one waitress & a man who appeared to have the job of bringing the menu to the table & pouring water. He was not intetested in taking drink orders for soda pop. That job fell to the waitress. There was only 1 waitress working on a Sunday mo

Reviewed on Nov 4, 2024

Marriott Tampa Westshore
3.5-star property

Marriott Tampa Westshore

8.8/10 Excellent! (1,001 reviews)

Dec 27 - Dec 29

2 night stay

Chicago (MDW) to Tampa (TPA)

Delta • Non-stop roundtrip • FirstClass
per person
found 1 day ago
Beautiful property. Beautiful staff. Expensive wifi. 8/10 Would highly recommend.

Reviewed on Aug 2, 2024

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More About Flying To Clearwater Beach from Chicago

Route Information for Flights from Chicago to Clearwater Beach

Origin Airport IATA Code
CHI
Destination Airport IATA Code
TPA
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Clearwater Beach

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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.