HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Clearwater Beach

$49+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Clearwater Beach with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 21, 2025.

Round-trip from

$90
(Priceline)

One-way from

$49
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$187
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. 5% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2025
Search Deals

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 January 21, 2025.

This Priceline deal was found by Cheapflights users on 1/21. 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.
Sat 3/13:25 pmORD - TPA
Nonstop2h 48mMultiple Airlines
Thu 3/66:55 amTPA - ORD
Nonstop3h 05mMultiple Airlines
Deal found 1/21$90
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/27:00 amORD - TPA
Nonstop2h 48mFrontier
Thu 2/63:20 pmTPA - ORD
1 stop8h 07mFrontier
Deal found 1/21$91
This Frontier deal was found by Cheapflights users on 1/19. 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.
Mon 2/242:41 pmMDW - TPA
Nonstop2h 42mFrontier
Sat 3/18:57 pmTPA - MDW
Nonstop2h 54mFrontier
Deal found 1/19$91
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/210:29 amORD - TPA
Nonstop2h 49mSpirit Airlines
Wed 2/512:16 pmTPA - ORD
Nonstop3h 07mSpirit Airlines
Deal found 1/21$92
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/164:56 pmORD - TPA
1 stop5h 26mDelta
Tue 4/226:15 amTPA - ORD
1 stop7h 24mDelta
Deal found 1/21$197
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/186:00 amMDW - TPA
1 stop7h 06mDelta
Tue 2/254:44 pmTPA - MDW
1 stop6h 36mDelta
Deal found 1/21$197
This Southwest deal was found by Cheapflights users on 1/19. 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 2/185:25 amMDW - TPA
Nonstop2h 40mSouthwest
Fri 2/218:25 pmTPA - MDW
Nonstop2h 40mSouthwest
Deal found 1/19$203
This Southwest deal was found by Cheapflights users on 1/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/204:00 pmORD - TPA
1 stop6h 35mSouthwest
Thu 2/275:35 amTPA - ORD
2 stops9h 25mSouthwest
Deal found 1/21$238

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 2,558,603 searches. Data last updated January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sat 3/1

3:25 pm-7:13 pm

Nonstop2h 48m

Tampa

Thu 3/6

6:55 am-9:00 am

Nonstop3h 05m

$90

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sun 2/2

7:00 am-10:48 am

Nonstop2h 48m

Tampa

Thu 2/6

3:20 pm-10:27 pm

1 stop8h 07m

$91

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Mon 2/24

2:41 pm-6:23 pm

Nonstop2h 42m

Tampa

Sat 3/1

8:57 pm-10:51 pm

Nonstop2h 54m

$91

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sun 2/2

7:26 am-11:11 am

Nonstop2h 45m

Tampa

Sat 2/8

12:16 pm-2:23 pm

Nonstop3h 07m

$93

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Wed 2/26

5:45 am-2:06 pm

1 stop7h 21m

Tampa

Tue 3/4

5:47 pm-11:49 pm

1 stop7h 02m

$197

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 2/18

12:44 pm-8:21 pm

1 stop6h 37m

Tampa

Thu 2/27

8:30 am-1:05 pm

1 stop5h 35m

$197

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 2/18

5:25 am-9:05 am

Nonstop2h 40m

Tampa

Fri 2/21

8:25 pm-10:05 pm

Nonstop2h 40m

$203

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Thu 2/20

7:30 am-6:50 pm

1 stop10h 20m

Tampa

Sat 2/22

6:10 am-4:45 pm

2 stops11h 35m

$212

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Tue 2/11

7:26 am-11:11 am

Nonstop2h 45m

$49

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Tue 2/18

6:20 am-10:08 am

Nonstop2h 48m

$52

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 20 results
1
2

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 January 17, 2025.

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, 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 January 21, 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 January 21, 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. Monday 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 January 21, 2025.

The most flights from CHI to CW9 are scheduled on a Monday (69 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 January 21, 2025.
Read reviews from past customers who have flown Frontier, Southwest and Delta 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
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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
7.4
Good
3,201 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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.

United Airlines
7.4
Good
8,985 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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.

Sun Country Air
7.0
Good
386 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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 Spirit Airlines ($49), Frontier ($52), and Southwest ($89).

  • 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 Azul (89%), Southwest (89%) and Brussels Airlines (84%).

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

    On average you can expect to pay $535 for a flight from Chicago to Clearwater Beach. The cheapest flight overall is $55 while the most popular route, (Chicago O'Hare Intl - Tampa) is currently priced at $75.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Clearwater Beach

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
O'Hare Intl to Tampa flights
Midway to Orlando flights
O'Hare Intl to Fort Myers flights
Midway to Miami flights
O'Hare Intl to West Palm Beach flights
Midway to Tampa flights
O'Hare Intl to Sarasota flights
Midway to Fort Myers flights
O'Hare Intl to Key West flights
Midway to Fort Lauderdale flights
O'Hare Intl to Jacksonville flights
St. Louis to Orlando flights
O'Hare Intl to Pensacola flights
Midway to West Palm Beach flights
St. Louis to Miami flights
O'Hare Intl to Panama City flights
St. Louis to Fort Myers flights
Midway to Key West flights
St. Louis to Fort Lauderdale flights
St. Louis to Tampa flights
Midway to Sarasota flights
Moline to Fort Myers flights
Moline to Orlando flights
O'Hare Intl to Daytona Beach flights
St. Louis to Sarasota flights
Midway to Panama City flights
O'Hare Intl to Melbourne flights
St. Louis to Key West flights
O'Hare Intl to Valparaiso flights
Peoria to Fort Myers flights
Midway to Jacksonville flights
Midway to Pensacola flights
St. Louis to Panama City flights
Rockford to St Petersburg flights
St. Louis to West Palm Beach flights
Peoria to Fort Lauderdale flights
Moline to Miami flights
Moline to Tampa flights
Rockford to Orlando Sanford Intl flights
St. Louis to Jacksonville flights
Peoria to Orlando flights
St. Louis to Pensacola flights
O'Hare Intl to St Petersburg flights
Midway to Daytona Beach flights
Moline to Fort Lauderdale flights
Moline to Pensacola flights
O'Hare Intl to Tallahassee flights

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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$42Average$177FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$165FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$103Average$206FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$146Average$325FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$158Average$362FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$171Average$416FlexibilityNo cancel feeOn-time63%
DeltaCheapest$195Average$392FlexibilityNo cancel feeOn-timeN/A
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.