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Clearwater Beach

$68+ 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 7/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Clearwater Beach are usually found in January or September, booked 75 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

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 June 18, 2025.

Round-trip from

$126
(Trip.com)

One-way from

$68
(FlightHub)

Popular in

March

Cheapest in

January

Average price

$261
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. 1% potential increase in price ($4 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 June 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 June 18, 2025.

This Trip.com deal was found by Cheapflights users on 6/17. 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.
Wed 7/98:50 amORD - TPA
Nonstop2h 47mSpirit Airlines
Sat 7/121:32 pmTPA - ORD
Nonstop3h 10mSpirit Airlines
Deal found 6/17$126
This Cheapflightsfares deal was found by Cheapflights users on 6/17. 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 8/45:30 pmORD - TPA
Nonstop2h 52mFrontier
Thu 8/2112:17 pmTPA - ORD
Nonstop3h 08mFrontier
Deal found 6/17$127
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:02 pmORD - TPA
Nonstop2h 50mAmerican Airlines
Wed 10/296:50 pmTPA - ORD
Nonstop3h 07mAmerican Airlines
Deal found 6/17$157
This Southwest deal was found by Cheapflights users on 6/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/135:30 pmMDW - TPA
Nonstop2h 35mSouthwest
Sat 9/207:20 amTPA - MDW
Nonstop2h 40mSouthwest
Deal found 6/15$157
This Cheapflightsfares deal was found by Cheapflights users on 6/15. 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.
Thu 7/103:58 pmMDW - TPA
Nonstop2h 41mFrontier
Sun 7/138:32 pmTPA - MDW
Nonstop2h 52mFrontier
Deal found 6/15$160
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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 8/85:28 pmORD - TPA
Nonstop2h 52mMultiple Airlines
Sat 8/168:13 amTPA - ORD
Nonstop2h 58mMultiple Airlines
Deal found 6/16$161
This United Airlines deal was found by Cheapflights users on 6/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/97:30 amORD - TPA
Nonstop2h 51mUnited Airlines
Sat 8/167:30 amTPA - ORD
Nonstop3h 04mUnited Airlines
Deal found 6/16$167
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:45 pmORD - TPA
1 stop5h 25mSouthwest
Mon 9/85:40 amTPA - ORD
1 stop6h 05mSouthwest
Deal found 6/16$177
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/26:15 pmORD - TPA
1 stop4h 59mDelta
Sat 8/96:00 amTPA - ORD
1 stop7h 50mDelta
Deal found 6/18$197
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/136:04 amMDW - TPA
1 stop4h 23mDelta
Wed 8/134:13 pmTPA - MDW
1 stop6h 36mDelta
Deal found 6/16$198

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 June 18, 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 7/9

8:50 am-12:37 pm

Nonstop2h 47m

Tampa

Sat 7/12

1:32 pm-3:42 pm

Nonstop3h 10m

$126

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Mon 8/4

5:30 pm-9:22 pm

Nonstop2h 52m

Tampa

Thu 8/21

12:17 pm-2:25 pm

Nonstop3h 08m

$127

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sat 8/30

6:10 pm-10:00 pm

Nonstop2h 50m

Tampa

Tue 9/2

7:00 am-9:06 am

Nonstop3h 06m

$157

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 9/13

5:30 pm-9:05 pm

Nonstop2h 35m

Tampa

Sat 9/20

7:20 am-9:00 am

Nonstop2h 40m

$157

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 7/10

3:58 pm-7:39 pm

Nonstop2h 41m

Tampa

Sun 7/13

8:32 pm-10:24 pm

Nonstop2h 52m

$160

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Fri 8/8

5:28 pm-9:20 pm

Nonstop2h 52m

Tampa

Mon 8/11

1:32 pm-3:42 pm

Nonstop3h 10m

$161

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sat 8/9

7:30 am-11:21 am

Nonstop2h 51m

Tampa

Sat 8/16

7:30 am-9:34 am

Nonstop3h 04m

$167

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Thu 9/4

5:45 pm-12:10 am

1 stop5h 25m

Tampa

Mon 9/8

5:40 am-10:45 am

1 stop6h 05m

$177

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sat 8/2

6:15 pm-12:14 am

1 stop4h 59m

Tampa

Sat 8/9

6:00 am-12:50 pm

1 stop7h 50m

$197

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 8/13

6:04 am-11:27 am

1 stop4h 23m

Tampa

Wed 8/13

4:13 pm-9:49 pm

1 stop6h 36m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

Showing 1-10 of 22 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 June 13, 2025.

The best time to book flights from Chicago to Clearwater Beach is 75 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 June 18, 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 June 15, 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 June 18, 2025.

The most flights from CHI to CW9 are scheduled on a Monday (71 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 on average).

Rainfall in Clearwater Beach by month

Plan your trip to Clearwater Beach by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Clearwater Beach ranges from 1.6 - 7.8 inches per month. August is typically the wettest month, when rainfall can reach 7.8 in. November is typically the driest time to visit Clearwater Beach when rainfall is around 1.6 in.

Temperature in Clearwater Beach by month

Plan your trip to Clearwater Beach by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Clearwater Beach, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 June 18, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Chicago to Clearwater Beach. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

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
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

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.
Delta
8.0
Very good
7,964 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

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
8,810 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

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
10,000 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

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.
Sun Country Air
6.9
Okay
345 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

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.

  • 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 Spirit Airlines ($68), United Airlines ($79), and Southwest ($79).

  • 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 (93%), Azul (89%) and United Airlines (87%).

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

    On average you can expect to pay $508 for a flight from Chicago to Clearwater Beach. The cheapest flight overall is $53 while the most popular route, (Chicago O'Hare Intl - Tampa) is currently priced at $118.

  • 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.

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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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$178FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$64Average$177FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$88Average$195FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$156Average$382FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$341FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$181Average$392FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$369FlexibilityNo cancel feeOn-timeN/A

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