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Clearwater Beach

$54+ Cheap flights from Chicago (CHI) to Clearwater Beach, FL

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jan 2 — Jan 91
Fri 1/2
Fri 1/9
1 adult, Economy
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Find cheap flights from Chicago to Clearwater Beach with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Clearwater Beach are usually found in January or September, booked 32 days in advance, depart on a Wednesday or Thursday and return on a Friday

Cheap flight deals from Chicago to Clearwater Beach

Cheapest flights from Chicago to Clearwater Beach
Explore the most affordable flight options available from Chicago to Clearwater Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/94:22 pmORD - TPA
1 stop6h 07mFrontier
Sun 1/111:15 pmTPA - ORD
Nonstop3h 13mFrontier
Deal found 12/1$105
This WAYA deal was found by Cheapflights users on 12/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/94:22 pmORD - TPA
1 stop6h 07mFrontier
Wed 12/105:45 amTPA - ORD
1 stop9h 46mFrontier
Deal found 12/2$107
This Expedia deal was found by Cheapflights users on 12/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:34 pmORD - TPA
Nonstop2h 43mSpirit Airlines
Wed 1/710:41 amTPA - ORD
Nonstop2h 58mSpirit Airlines
Deal found 12/2$108
This Kiwi.com deal was found by Cheapflights users on 12/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/94:22 pmORD - TPA
1 stop6h 07mFrontier
Wed 12/175:45 amTPA - ORD
1 stop9h 46mFrontier
Deal found 12/2$110
This CheapOair deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/231:34 pmORD - TPA
Nonstop2h 43mSpirit Airlines
Thu 1/82:57 pmTPA - ORD
Nonstop3h 01mSpirit Airlines
Deal found 12/3$111
This Kiwi.com deal was found by Cheapflights users on 12/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/148:45 amORD - TPA
Nonstop3h 04mFrontier
Sun 1/111:15 pmTPA - ORD
Nonstop3h 13mFrontier
Deal found 12/1$112
This Kiwi.com deal was found by Cheapflights users on 12/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1511:44 amORD - TPA
1 stop11h 32mFrontier
Thu 1/81:15 pmTPA - ORD
Nonstop3h 13mFrontier
Deal found 12/1$113
This Kiwi.com deal was found by Cheapflights users on 12/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/148:45 amORD - TPA
Nonstop3h 04mMultiple Airlines
Sat 1/102:57 pmTPA - ORD
Nonstop3h 01mMultiple Airlines
Deal found 12/1$114
This Kiwi.com deal was found by Cheapflights users on 12/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:34 pmORD - TPA
Nonstop2h 43mMultiple Airlines
Sat 12/2010:19 pmTPA - ORD
Nonstop3h 12mMultiple Airlines
Deal found 12/1$115
This Kiwi.com deal was found by Cheapflights users on 12/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:34 pmORD - TPA
Nonstop2h 43mMultiple Airlines
Wed 1/76:12 pmTPA - ORD
1 stop5h 27mMultiple Airlines
Deal found 12/1$118
This Mytrip deal was found by Cheapflights users on 11/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:25 pmORD - TPA
1 stop13h 39mMultiple Airlines
Mon 1/122:57 pmTPA - ORD
Nonstop3h 01mMultiple Airlines
Deal found 11/30$119
This Kiwi.com deal was found by Cheapflights users on 12/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/92:49 pmMDW - TPA
1 stop7h 40mFrontier
Thu 12/115:45 amTPA - MDW
1 stop13h 23mFrontier
Deal found 12/1$126

Find flight deals from Chicago to Clearwater Beach

Keep the following information in mind while searching for Chicago to Clearwater Beach flight deals. Data was last updated December 3, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$106
(American Airlines)

One-way from

$54
(WAYA)

Popular in

November

Cheapest in

January

Average price

$281
Provider with most accurate pricing for Chicago (CHI)-Tampa flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Tampa flights.
Search Deals
From Chicago (CHI) to Clearwater Beach
Search Deals
One-way flight from Chicago (CHI) to Clearwater Beach
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Clearwater Beach that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 3, 2025.
Use the filters below to find and compare flights from Chicago to Clearwater Beach that are best for you.

Fly from

Chicago

Fly to

Clearwater Beach

Route

Depart

Return

Price

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 1/10

5:35 pm-9:10 pm

Nonstop2h 35m

Tampa

Thu 1/15

6:40 am-8:25 am

Nonstop2h 45m

$132

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sun 1/25

6:10 pm-10:09 pm

Nonstop2h 59m

Tampa

Thu 1/29

12:25 pm-2:28 pm

Nonstop3h 03m

$149

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sun 2/1

10:56 am-2:55 pm

Nonstop2h 59m

Tampa

Thu 2/5

12:25 pm-2:28 pm

Nonstop3h 03m

$149

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Mon 2/2

5:40 pm-9:15 pm

Nonstop2h 35m

Tampa

Sat 2/7

4:50 pm-6:40 pm

Nonstop2h 50m

$155

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Fri 1/23

3:45 pm-7:38 pm

Nonstop2h 53m

Tampa

Sun 1/25

7:30 am-9:32 am

Nonstop3h 02m

$162

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 2/7

5:35 pm-9:10 pm

Nonstop2h 35m

Tampa

Mon 2/9

6:40 am-8:25 am

Nonstop2h 45m

$163

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 2/10

10:05 am-4:20 pm

1 stop5h 15m

Tampa

Sat 2/21

5:40 pm-7:25 pm

Nonstop2h 45m

$166

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sun 1/11

9:35 am-2:45 pm

1 stop4h 10m

Tampa

Thu 1/15

6:50 am-11:05 am

1 stop5h 15m

$169

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Fri 1/9

7:15 am-11:08 am

Nonstop2h 53m

Tampa

Mon 1/12

12:25 pm-2:28 pm

Nonstop3h 03m

$171

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 1/8

1:15 pm-7:45 pm

1 stop5h 30m

Tampa

Sat 1/24

4:50 pm-6:40 pm

Nonstop2h 50m

$173

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

Showing 1-10 of 45 results
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Best time to book a flight from Chicago to Clearwater Beach

Have a flexible travel schedule? Discover the best time to fly to Clearwater Beach from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Clearwater Beach

How far ahead should I book a flight from Chicago to Clearwater Beach?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Clearwater Beach. Price data was last updated on November 28, 2025.

The best time to book flights from Chicago to Clearwater Beach is 32 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Clearwater Beach?

Currently, March is the cheapest month in which you can book a flight from Chicago to Clearwater Beach (average of $44). Flying from Chicago to Clearwater Beach in October is currently the most expensive (average of $83). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to CW9?

Find hourly flight availability from Chicago to Clearwater Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 3, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 28% on flights from Chicago to Clearwater Beach by exploring options for tickets in the afternoon.

What is the cheapest day to fly from Chicago to Clearwater Beach?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Clearwater Beach. Price data was last updated on November 29, 2025.

Travelers seeking maximum savings on their Chicago to Clearwater Beach flight should consider departing on Tuesday evenings when fares are most often at their lowest. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Clearwater Beach

Explore weekly flight availability from Chicago to Clearwater Beach. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 3, 2025.

The most flights from CHI to CW9 are scheduled on a Wednesday (58 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).

How much does it cost to fly round-trip from Chicago to Clearwater Beach?

Reviews of airlines servicing Clearwater Beach

Get insights into the airlines that provide service to Clearwater Beach. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Clearwater Beach. Reviews last updated December 3, 2025.
Read through reviews of airlines operating flights from Chicago to Clearwater Beach, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
9,065 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.2
Good
11,044 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Spirit Airlines
6.3
Okay
8,161 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.8
Fair
3,092 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Clearwater Beach. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Clearwater Beach?

    There are many flights that can get you from Chicago to Clearwater Beach in 2h 35m. Fly via Southwest, United Airlines, or JetBlue to get the fastest option. Airlines will cover a distance of 998 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to Clearwater Beach one-way?

    The cheapest airlines for a one-way flight from Chicago to Clearwater Beach are Frontier ($38), Spirit Airlines ($43), and Southwest ($68).

  • What are the most reliable airlines from Chicago to Clearwater Beach?

    The top 3 most reliable airlines when flying from Chicago to Clearwater Beach are Copa Airlines (87%), United Airlines (83%) and Azul (82%).

  • What are the cheapest flights from Chicago to Clearwater Beach?

    On average you can expect to pay $455 for a flight from Chicago to Clearwater Beach. The cheapest flight overall is $42 while the most popular route, (Chicago O'Hare Intl - Tampa) is currently priced at $50.

  • Can I find deals for flights from Chicago to Clearwater Beach that include hotel bookings?

    Yes. In addition to deals on Chicago to Clearwater Beach flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Clearwater Beach?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Clearwater Beach.

  • Can I find deals for business class flights from Chicago to Clearwater Beach?

    Yes. Cheapflights offers flight deals from Chicago to Clearwater Beach by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Clearwater Beach?

    Currently, March is the cheapest month in which you can book a flight from Chicago to Clearwater Beach (average of $44). Flying from Chicago to Clearwater Beach in October is currently the most expensive (average of $83). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 8 airlines flying from Chicago to Clearwater Beach

Discover the top 8 airlines that operate flights from Chicago to Clearwater Beach. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$198FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$178FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$96Average$192FlexibilityNo cancel feeOn-time88%
DeltaCheapest$149Average$383FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$153Average$360FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$156Average$317FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$157Average$373FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$195Average$296FlexibilityNo cancel feeOn-time62%

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