$80 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.
MDW
Midway Intl.
TPA
Tampa Intl.
$266 Roundtrip, just found
$266
Roundtrip
just found
ORD
O'Hare Intl.
TPA
Tampa Intl.
$322 Roundtrip, just found
$322
Roundtrip
just found
RFD
Greater Rockford
TPA
Tampa Intl.
$406 Roundtrip, found 6 hours ago
$406
Roundtrip
found 6 hours ago
Airfares from $80 One Way, $150 Round Trip from Chicago to Clearwater
Prices starting at $150 for return flights and $80 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.
ORD
Chicago
TPA
Tampa
$150 Roundtrip, found 15 hours ago
$150
Roundtrip
found 15 hours ago
ORD
Chicago
TPA
Tampa
$155 Roundtrip, found 5 days ago
$155
Roundtrip
found 5 days ago
ORD
Chicago
TPA
Tampa
$160 Roundtrip, found 2 hours ago
$160
Roundtrip
found 2 hours ago
MDW
Chicago
TPA
Tampa
$175 Roundtrip, found 4 hours ago
$175
Roundtrip
found 4 hours ago
ORD
Chicago
TPA
Tampa
$175 Roundtrip, found 4 hours ago
$175
Roundtrip
found 4 hours ago
Clearwater economy flight packages
Price found within the past 48 hours. Click for updated prices.
2.5-star property
Pelican Pointe Clearwater Beach Hotel
9/10 Wonderful! (1,004 reviews)
Jul 10 - Jul 17
7 night stay
Chicago (CHI) to Tampa (TPA)
Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,105, price is now $749 per person
$749
per person
found 1 day ago
Every thing of the above was good
Reviewed on Nov 26, 2025
2.0-star property
ChartHouse Clearwater Beach Marina Hotel
9.6/10 Exceptional! (1,034 reviews)
Jul 10 - Jul 17
7 night stay
Chicago (CHI) to Tampa (TPA)
Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,365, price is now $842 per person
$842
per person
found 1 day ago
Clean , nice location near beach
Reviewed on May 14, 2026
4.0-star property
The Avalon Club
9.4/10 Exceptional! (538 reviews)
Jul 10 - Jul 17
7 night stay
Chicago (CHI) to Tampa (TPA)
Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,398, price is now $2,181 per person
$2,181
per person
found 1 day ago
A lot of attention to detail, high quality space with quality things like bedsheets, mattress and pillows. Above all.. incredible staff! Very friendly and thoughtful.
Reviewed on Mar 28, 2026
Clearwater business class flight packages
Price found within the past 48 hours. Click for updated prices.
2.0-star property
ChartHouse Clearwater Beach Marina Hotel
9.6/10 Exceptional! (1,034 reviews)
Jul 10 - Jul 17
7 night stay
Chicago (CHI) to Tampa (TPA)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,591, price is now $1,130 per person
$1,130
per person
found 1 day ago
Clean , nice location near beach
Reviewed on May 14, 2026
4.0-star property
Ocean Club Treasure Island Hotel
9.6/10 Exceptional! (950 reviews)
Jul 10 - Jul 17
7 night stay
Chicago (CHI) to Tampa (TPA)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $2,563, price is now $1,634 per person
$1,634
per person
found 1 day ago
This place is gorgeous and I highly recommend. I gave 4 stars because the guy working the desk was not very smart. He overcharged us by $200. He gave me the wrong WiFi password.
I hope I get my money back.
Otherwise it was a beautiful stay.
Reviewed on May 12, 2026
3.5-star property
FUSION Resort Waterfront Suites
9.2/10 Wonderful! (1,174 reviews)
Jul 10 - Jul 17
7 night stay
Chicago (CHI) to Tampa (TPA)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,605, price is now $1,220 per person
$1,220
per person
found 1 day ago
Room wasn’t ready when we arrived, we had to wait 45 minutes. The front desk lady didn’t have a name tag so I couldn’t addressed her properly. She didn’t have good communication skills. Richard was awesome he had to take over and helped her. Other than that was a great clean place to stay.
Reviewed on Jul 2, 2024
Clearwater first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
The Residences at Siesta Key Beach by Hyatt Vacation Club
9.8/10 Exceptional! (347 reviews)
Jul 10 - Jul 17
7 night stay
Chicago (CHI) to Tampa (TPA)
Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,577, price is now $3,037 per person
$3,037
per person
found 1 day ago
More hotel, less resort feel, and on-site food options were limited but good. Gym was basic.
Reviewed on May 14, 2026
3.0-star property
Cedar Cove Resort and Cottages
9.2/10 Wonderful! (515 reviews)
Jul 10 - Jul 17
7 night stay
Chicago (CHI) to Tampa (TPA)
Delta • Non-stop roundtrip • FirstClass
Price was $2,437, price is now $1,632 per person
$1,632
per person
found 1 day ago
Extremely clean. Friendly, helpful staff that went above and beyond. I traveled with my teenage daughter and her friend and we never once felt unsafe. I was fine using the free trolley transportation up and down the island, but the girls talked me into renting a golf cart. That did provide more freedom for our short time there. The resort has golf carts for rent. We will definitely be back!
Reviewed on Aug 10, 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
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- Hotels near Sand Key Park
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- 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.