$81 Cheap flight deals from Chicago (CHI) to Clearwater Beach (TPA)

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.

Fri, Oct 2 - Wed, Oct 7
RFD
Greater Rockford
PIE
St. Petersburg-Clearwater Intl.
$242 Roundtrip, found 3 days ago
$242
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Fri, Oct 2 from Greater Rockford to St. Petersburg-Clearwater Intl., returning Wed, Oct 7, priced at $242 found 3 days ago
Fri, Oct 2 - Wed, Oct 7
RFD
Greater Rockford
PIE
St. Petersburg-Clearwater Intl.
$242 Roundtrip, found 3 days ago
$242
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Fri, Oct 2 from Greater Rockford to St. Petersburg-Clearwater Intl., returning Wed, Oct 7, priced at $242 found 3 days ago
Sat, Oct 3 - Tue, Oct 6
ORD
O'Hare Intl.
TPA
Tampa Intl.
$294 Roundtrip, found 19 hours ago
$294
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, Oct 3 from O'Hare Intl. to Tampa Intl., returning Tue, Oct 6, priced at $294 found 19 hours ago
Sat, Oct 3 - Sat, Oct 10
MDW
Midway Intl.
TPA
Tampa Intl.
$294 Roundtrip, found 3 hours ago
$294
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Oct 3 from Midway Intl. to Tampa Intl., returning Sat, Oct 10, priced at $294 found 3 hours ago

Airfares from $81 One Way, $116 Round Trip from Chicago to Clearwater Beach

Prices starting at $116 for return flights and $81 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.

Mon, Feb 22 - Thu, Feb 25
ORD
Chicago
TPA
Tampa
$116 Roundtrip, found 3 days ago
$116
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Feb 22 from Chicago to Tampa, returning Thu, Feb 25, priced at $116 found 3 days ago
Mon, Jan 11 - Fri, Jan 15
RFD
Rockford
PIE
St. Petersburg
$125 Roundtrip, found 3 days ago
$125
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Mon, Jan 11 from Rockford to St. Petersburg, returning Fri, Jan 15, priced at $125 found 3 days ago
Tue, Feb 2 - Sat, Feb 6
MDW
Chicago
TPA
Tampa
$195 Roundtrip, found 3 hours ago
$195
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Tue, Feb 2 from Chicago to Tampa, returning Sat, Feb 6, priced at $195 found 3 hours ago
Tue, Feb 2 - Sat, Feb 6
MDW
Chicago
TPA
Tampa
$277 Roundtrip, found 3 hours ago
$277
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Tue, Feb 2 from Chicago to Tampa, returning Sat, Feb 6, priced at $277 found 3 hours ago
Sat, Oct 17 - Tue, Oct 20
ORD
Chicago
TPA
Tampa
$277 Roundtrip, found 1 hour ago
$277
Roundtrip
found 1 hour ago
Select United flight, departing Sat, Oct 17 from Chicago to Tampa, returning Tue, Oct 20, priced at $277 found 1 hour ago

Clearwater Beach economy flight packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Tampa North by IHG
3.0-star property

Holiday Inn Tampa North by IHG

8.6/10 Excellent! (896 reviews)

Nov 7 - Nov 15

8 night stay

Chicago (CHI) to Tampa (TPA)

American Airlines • Coach

Tampa (TPA) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $924, price is now $655 per person
$655
per person
found 12 hours ago
We checked in early because we were going to Howl-o-Screams at Busch Gardens. Staff was great. Hotel location was on the way to park. Rooms were really nice. Will use the again in the future.

Reviewed on Sep 25, 2026

Cedar Cove Resort and Cottages
3.0-star property

Cedar Cove Resort and Cottages

9.2/10 Wonderful! (591 reviews)

Nov 12 - Nov 15

3 night stay

Chicago (ORD) to Tampa (TPA)

American Airlines • Coach

Tampa (TPA) to Chicago (ORD)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,209, price is now $833 per person
$833
per person
found 1 day ago

Saddlebrook Resort
4.0-star property

Saddlebrook Resort

8/10 Very Good! (158 reviews)

Nov 7 - Nov 15

8 night stay

Chicago (CHI) to Tampa (TPA)

American Airlines • Coach

Tampa (TPA) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,022, price is now $723 per person
$723
per person
found 20 hours ago

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