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Clearwater Beach

$53+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Oct 24 — Oct 311
Fri 10/24
Fri 10/31
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Clearwater Beach are usually found in January or April, booked 61 days in advance, depart on a Wednesday or Thursday and return on a Friday

Cheap 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 September 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$100
(CheapOair)

One-way from

$53
(Vakatrip)

Popular in

March

Cheapest in

January

Average price

$197
Provider with most accurate pricing for Chicago (CHI)-Tampa flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Tampa flights.
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From Chicago (CHI) to Clearwater Beach
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One-way flight from Chicago (CHI) to Clearwater Beach
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Highest demand for flights based on searches. 0% potential increase in price ($0 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 24, 2025.

This CheapOair deal was found by Cheapflights users on 9/21. 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.
Mon 10/209:45 amMDW - TPA
Nonstop2h 37mFrontier
Mon 10/272:22 pmTPA - MDW
Nonstop2h 47mFrontier
Deal found 9/21$100
This CheapOair deal was found by Cheapflights users on 9/21. 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.
Fri 10/317:50 amMDW - TPA
Nonstop2h 34mFrontier
Sun 11/210:41 pmTPA - MDW
Nonstop2h 49mFrontier
Deal found 9/21$102
This Trip.com deal was found by Cheapflights users on 9/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:06 pmMDW - TPA
Nonstop2h 35mFrontier
Fri 11/143:11 pmTPA - MDW
Nonstop2h 46mFrontier
Deal found 9/22$104
This Priceline deal was found by Cheapflights users on 9/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:00 pmORD - TPA
Nonstop2h 39mMultiple Airlines
Sat 10/181:45 pmTPA - ORD
Nonstop3h 00mMultiple Airlines
Deal found 9/24$105
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:21 amMDW - TPA
Nonstop2h 36mFrontier
Mon 10/202:22 pmTPA - MDW
Nonstop2h 47mFrontier
Deal found 9/24$105
This Priceline deal was found by Cheapflights users on 9/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:21 amMDW - TPA
Nonstop2h 36mFrontier
Fri 10/172:22 pmTPA - MDW
Nonstop2h 47mFrontier
Deal found 9/21$106
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:00 pmORD - TPA
Nonstop2h 39mSpirit Airlines
Sat 10/188:19 amTPA - ORD
Nonstop2h 55mSpirit Airlines
Deal found 9/23$107
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/153:12 pmORD - TPA
1 stop7h 32mFrontier
Sat 10/181:45 pmTPA - ORD
Nonstop3h 00mFrontier
Deal found 9/24$108
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:25 pmORD - TPA
Nonstop2h 37mSpirit Airlines
Sun 11/211:26 amTPA - ORD
Nonstop2h 53mSpirit Airlines
Deal found 9/24$109
This Frontier deal was found by Cheapflights users on 9/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/188:40 amORD - TPA
Nonstop2h 55mFrontier
Wed 10/227:30 amTPA - ORD
1 stop10h 10mFrontier
Deal found 9/24$110
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 10/125:50 amORD - TPA
Nonstop2h 55mMultiple Airlines
Tue 10/218:13 amTPA - ORD
Nonstop2h 55mMultiple Airlines
Deal found 9/24$111
This Trip.com deal was found by Cheapflights users on 9/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/179:45 amMDW - TPA
Nonstop2h 37mFrontier
Mon 10/202:22 pmTPA - MDW
Nonstop2h 47mFrontier
Deal found 9/23$111

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 September 24, 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

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Wed 10/15

11:00 am-7:32 pm

1 stop7h 32m

Tampa

Sat 10/18

1:45 pm-3:45 pm

Nonstop3h 00m

$108

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Thu 10/2

8:05 am-12:05 pm

Nonstop3h 00m

Tampa

Sun 10/5

5:01 am-7:10 am

Nonstop3h 09m

$114

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Thu 11/6

7:05 am-10:49 am

Nonstop2h 44m

Tampa

Sun 11/9

6:00 am-10:38 am

1 stop5h 38m

$121

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Thu 10/23

5:50 pm-11:36 pm

1 stop4h 46m

Tampa

Thu 10/30

6:10 am-10:41 am

1 stop5h 31m

$141

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Thu 10/30

11:11 am-7:56 pm

1 stop7h 45m

Tampa

Tue 11/11

7:50 am-3:39 pm

1 stop8h 49m

$143

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Mon 12/15

7:10 am-10:45 am

Nonstop2h 35m

Tampa

Wed 12/17

7:15 pm-9:00 pm

Nonstop2h 45m

$147

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sat 11/8

11:15 am-3:08 pm

Nonstop2h 53m

Tampa

Tue 11/11

7:30 am-9:29 am

Nonstop2h 59m

$147

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 12/16

7:10 am-10:45 am

Nonstop2h 35m

Tampa

Thu 12/18

9:40 am-11:25 am

Nonstop2h 45m

$147

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Tue 11/11

2:15 pm-10:35 pm

1 stop7h 20m

Tampa

Tue 11/18

12:45 pm-2:45 pm

Nonstop3h 00m

$147

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 12/3

2:55 pm-6:30 pm

Nonstop2h 35m

Tampa

Thu 12/4

1:05 pm-5:35 pm

1 stop5h 30m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/23

Showing 1-10 of 42 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 September 19, 2025.

The best time to book flights from Chicago to Clearwater Beach is 61 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, May is the cheapest month in which you can book a flight from Chicago to Clearwater Beach (average of $206). Flying from Chicago to Clearwater Beach in November is currently the most expensive (average of $289). 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 September 24, 2025.

When flying from Chicago to Clearwater Beach, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 21, 2025.

Travelers seeking maximum savings on their Chicago to Clearwater Beach flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday 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 September 24, 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 (18 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 September 24, 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
4,244 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

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
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

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
8,928 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

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
8,042 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

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
3,163 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

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 Frontier or Southwest 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 most reliable airlines from Chicago to Clearwater Beach?

    The top 3 most reliable airlines when flying from Chicago to Clearwater Beach are Copa Airlines (84%), Spirit Airlines (82%) and Air Canada (78%).

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

    On average you can expect to pay $466 for a flight from Chicago to Clearwater Beach. The cheapest flight overall is $49 while the most popular route, (Chicago O'Hare Intl - Tampa) is currently priced at $91.

  • 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, May is the cheapest month in which you can book a flight from Chicago to Clearwater Beach (average of $206). Flying from Chicago to Clearwater Beach in November is currently the most expensive (average of $289). 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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Alternative routes for Chicago to Clearwater Beach

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Chicago to Clearwater Beach

Discover the top 7 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 September 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$202FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$177FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$89Average$184FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$157Average$372FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$159Average$341FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$161Average$376FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$363FlexibilityNo cancel feeOn-timeN/A

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