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$38+ 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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Nov 19 — Nov 261
1 adult
Tue 11/19
Tue 11/26
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The best prices from Chicago to Clearwater Beach are usually found in September or April, booked 23 days in advance, depart on a Tuesday or Wednesday and return on a Saturday

Cheap flight deals from Chicago to Clearwater Beach

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Clearwater Beach (CW9). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 14, 2024.

Popular in

March

Cheapest in

September

Round-trip from

$104
(eDestinos)

One-way from

$38
(Cheapflightsfares)
High demand for flights, 26% potential price rise
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Best time to find cheap flights, 22% potential price drop
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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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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 November 14, 2024.

This eDestinos deal was found by Cheapflights users on 11/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1311:25 amORD - TPA
Nonstop2h 50mSpirit Airlines
Fri 12/205:49 amTPA - ORD
Nonstop2h 58mSpirit Airlines
Deal found 11/13$104
This Cheapflightsfares deal was found by Cheapflights users on 11/14. 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.
Tue 12/175:45 amORD - TPA
Nonstop2h 56mFrontier
Tue 12/248:56 amTPA - ORD
1 stop8h 32mFrontier
Deal found 11/14$109
This Cheapflightsfares deal was found by Cheapflights users on 11/13. 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 12/186:50 amMDW - TPA
Nonstop2h 46mFrontier
Wed 12/2511:31 amTPA - MDW
Nonstop2h 49mFrontier
Deal found 11/13$110
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Wed 12/1810:22 pmORD - TPA
1 stop8h 31mMultiple Airlines
Tue 12/315:49 amTPA - ORD
Nonstop2h 58mMultiple Airlines
Deal found 11/13$111
This Southwest deal was found by Cheapflights users on 11/14. 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.
Tue 12/39:25 amMDW - TPA
Nonstop2h 35mSouthwest
Sat 12/78:25 amTPA - MDW
Nonstop2h 45mSouthwest
Deal found 11/14$195
This Delta deal was found by Cheapflights users on 11/13. 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 12/111:30 pmMDW - TPA
1 stop6h 27mDelta
Mon 12/165:19 pmTPA - MDW
1 stop5h 47mDelta
Deal found 11/13$196
This Mytrip deal was found by Cheapflights users on 11/12. 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.
Fri 11/229:09 pmMDW - TPA
2 stops17h 03mMultiple Airlines
Sun 11/2410:25 amTPA - MDW
1 stop8h 36mMultiple Airlines
Deal found 11/12$284

Find flights from Chicago to Clearwater Beach within your budget

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 2,752,363 searches. Data last updated November 14, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Fri 12/13

11:25 am-3:15 pm

Nonstop2h 50m

Tampa

Fri 12/20

5:49 am-7:47 am

Nonstop2h 58m

$104

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Thu 1/16

3:56 pm-1:45 am

1 stop8h 49m

Tampa

Thu 1/23

3:20 pm-10:27 pm

1 stop8h 07m

$106

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 2/22

7:48 am-11:24 am

Nonstop2h 36m

Tampa

Sat 3/1

12:19 pm-2:02 pm

Nonstop2h 43m

$106

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Wed 12/18

10:22 pm-7:53 am

1 stop8h 31m

Tampa

Tue 12/31

5:49 am-7:47 am

Nonstop2h 58m

$111

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 1/30

7:40 am-11:20 am

Nonstop2h 40m

Tampa

Mon 2/3

2:30 pm-4:15 pm

Nonstop2h 45m

$179

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 2/11

12:44 pm-5:45 pm

1 stop4h 01m

Tampa

Sat 2/15

5:55 am-9:23 am

1 stop4h 28m

$196

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Wed 12/11

6:05 pm-9:57 pm

Nonstop2h 52m

Tampa

Wed 12/18

9:45 am-11:41 am

Nonstop2h 56m

$197

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Fri 1/17

7:00 am-3:44 pm

1 stop7h 44m

Tampa

Fri 1/24

11:25 am-5:18 pm

1 stop6h 53m

$226

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sun 2/9

8:45 am-12:31 pm

Nonstop2h 46m

$50

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Wed 1/1

10:22 pm-7:53 am

1 stop8h 31m

$52

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 23 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.

Travel insights for flights from Chicago to Clearwater Beach

Get recent, data-driven insights about flights from Chicago to Clearwater Beach including ideal travel times, pricing trends, and more.

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 8, 2024.

The best time to book flights from Chicago to Clearwater Beach is 23 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, December is the cheapest month in which you can book a flight from Chicago to Clearwater Beach (average of $203). Flying from Chicago to Clearwater Beach in November is currently the most expensive (average of $263). 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 November 14, 2024.

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 November 10, 2024.

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. 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 November 14, 2024.

The most flights from CHI to CW9 are scheduled on a Thursday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (34 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 November 14, 2024.
Read reviews from past customers who have flown Southwest, Frontier and Spirit Airlines from Chicago to Clearwater Beach. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,045 reviews

Entertainment

7.7

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

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
8.1
Very good
5,045 reviews
Southwest
8.1
Very good
5,045 reviews

Entertainment

7.7

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

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
8,788 reviews
Southwest
8.1
Very good
5,045 reviews

Entertainment

7.7

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

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.

Porter Airlines
7.7
Good
288 reviews
Southwest
8.1
Very good
5,045 reviews

Entertainment

7.7

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

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.

JetBlue
7.5
Good
3,447 reviews
Southwest
8.1
Very good
5,045 reviews

Entertainment

7.7

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

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.

Avelo Airlines
7.5
Good
74 reviews
Southwest
8.1
Very good
5,045 reviews

Entertainment

7.7

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

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 Frontier ($38), Spirit Airlines ($56), 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 Royal Jordanian (97%), Alaska Airlines (94%) and Spirit Airlines (94%).

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

    On average you can expect to pay $568 for a flight from Chicago to Clearwater Beach. The cheapest flight overall is $59 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, December is the cheapest month in which you can book a flight from Chicago to Clearwater Beach (average of $203). Flying from Chicago to Clearwater Beach in November is currently the most expensive (average of $263). 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 2,752,363 searches. Data last updated November 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$23Average$143FlexibilityNo cancel feeOn-time65%
FrontierCheapest$36Average$182FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$94Average$218FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$154Average$341FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$155Average$310FlexibilityNo cancel feeOn-time71%
DeltaCheapest$195Average$392FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$201Average$386FlexibilityNo cancel feeOn-time63%
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