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$69+ 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 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Clearwater Beach are usually found in September or October, booked 32 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 January 15, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$109
(Cheapflightsfares)

One-way from

$69
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$190
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. 14% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 15, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/14. 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.
Sun 2/110:07 am
ORD
-
TPA
Nonstop2h 47m
Spirit Airlines
Sat 2/72:57 pm
TPA
-
ORD
Nonstop3h 01m
Spirit Airlines
Deal found 1/14$109
This Expedia deal was found by Cheapflights users on 1/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2110:19 am
ORD
-
TPA
Nonstop2h 47m
Spirit Airlines
Wed 2/253:01 pm
TPA
-
ORD
Nonstop3h 02m
Spirit Airlines
Deal found 1/14$110
This Cheapflightsfares deal was found by Cheapflights users on 1/14. 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.
Mon 2/2310:19 am
ORD
-
TPA
Nonstop2h 47m
Spirit Airlines
Thu 2/263:01 pm
TPA
-
ORD
Nonstop3h 02m
Spirit Airlines
Deal found 1/14$111
This Expedia deal was found by Cheapflights users on 1/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/106:07 pm
ORD
-
TPA
1 stop5h 18m
Multiple Airlines
Sat 2/143:01 pm
TPA
-
ORD
Nonstop3h 02m
Multiple Airlines
Deal found 1/14$112
This Cheapflightsfares deal was found by Cheapflights users on 1/14. 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.
Sat 1/317:20 am
ORD
-
TPA
1 stop9h 13m
Spirit Airlines
Thu 2/52:57 pm
TPA
-
ORD
Nonstop3h 01m
Spirit Airlines
Deal found 1/14$113
This Mytrip deal was found by Cheapflights users on 1/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:17 am
ORD
-
TPA
Nonstop2h 47m
Spirit Airlines
Sat 5/233:09 pm
TPA
-
ORD
Nonstop3h 01m
Spirit Airlines
Deal found 1/14$114
This Kiwi.com deal was found by Cheapflights users on 1/13. 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.
Tue 2/2410:19 am
ORD
-
TPA
Nonstop2h 47m
Multiple Airlines
Wed 3/46:15 am
TPA
-
ORD
1 stop5h 36m
Multiple Airlines
Deal found 1/13$115
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/176:00 am
MDW
-
TPA
1 stop17h 25m
Frontier
Tue 2/246:15 am
TPA
-
MDW
1 stop13h 52m
Frontier
Deal found 1/14$116
This CheapOair deal was found by Cheapflights users on 1/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/38:10 am
ORD
-
TPA
1 stop10h 51m
Frontier
Thu 2/59:12 pm
TPA
-
ORD
Nonstop3h 04m
Frontier
Deal found 1/13$116
This Cheapflightsfares deal was found by Cheapflights users on 1/13. 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.
Thu 1/295:15 am
ORD
-
TPA
1 stop11h 18m
Spirit Airlines
Fri 2/62:57 pm
TPA
-
ORD
Nonstop3h 01m
Spirit Airlines
Deal found 1/13$117
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:22 pm
MDW
-
TPA
1 stop11h 03m
Frontier
Wed 2/254:12 pm
TPA
-
MDW
1 stop25h 04m
Frontier
Deal found 1/14$118
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:25 am
ORD
-
TPA
Nonstop2h 48m
Multiple Airlines
Wed 4/153:09 pm
TPA
-
ORD
Nonstop3h 01m
Multiple Airlines
Deal found 1/15$118

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 January 15, 2026.
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 3/7

5:00 am-8:35 am

Nonstop2h 35m

Tampa

Tue 3/10

3:00 pm-8:00 pm

1 stop6h 00m

$167

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sun 2/15

10:00 am-7:00 pm

1 stop8h 00m

Tampa

Sat 2/21

2:35 pm-11:21 pm

1 stop9h 46m

$179

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 2/3

2:10 pm-9:55 pm

1 stop6h 45m

Tampa

Wed 2/4

12:50 pm-6:35 pm

2 stops6h 45m

$182

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 2/11

8:20 am-4:10 pm

1 stop6h 50m

Tampa

Sat 2/14

6:00 am-11:55 am

1 stop6h 55m

$195

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 3/12

7:00 pm-12:10 am

1 stop4h 10m

Tampa

Tue 3/17

12:50 pm-5:05 pm

1 stop5h 15m

$195

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Mon 2/23

3:40 pm-10:40 pm

1 stop6h 00m

Tampa

Thu 2/26

6:40 am-8:25 am

Nonstop2h 45m

$196

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 3/24

6:25 am-1:52 pm

1 stop6h 27m

Tampa

Tue 3/31

6:05 am-12:29 pm

1 stop7h 24m

$197

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 4/1

6:25 am-2:46 pm

1 stop7h 21m

Tampa

Wed 4/8

6:05 am-12:29 pm

1 stop7h 24m

$197

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sun 2/22

6:45 am-2:48 pm

1 stop7h 03m

Tampa

Sat 3/7

6:55 pm-11:56 pm

1 stop6h 01m

$198

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Tue 3/17

11:10 am-5:50 pm

1 stop5h 40m

Tampa

Mon 3/23

6:59 pm-11:59 pm

1 stop6h 00m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Showing 1-10 of 40 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 January 9, 2026.

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, January is the cheapest month in which you can book a flight from Chicago to Clearwater Beach (average of $48). Flying from Chicago to Clearwater Beach in December is currently the most expensive (average of $89). 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 15, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 18% 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 January 10, 2026.

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 January 15, 2026.

The most flights from CHI to CW9 are scheduled on a Thursday (66 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 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 January 15, 2026.
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
4,258 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

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
4,258 reviews
Southwest
8.0
Very good
4,258 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

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
9,164 reviews
Southwest
8.0
Very good
4,258 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

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
11,136 reviews
Southwest
8.0
Very good
4,258 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

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
8,322 reviews
Southwest
8.0
Very good
4,258 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

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
5.7
Fair
3,057 reviews
Southwest
8.0
Very good
4,258 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

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 Southwest, JetBlue, or Delta 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 (79%), Volaris (78%) and Azul (78%).

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

    On average you can expect to pay $603 for a flight from Chicago to Clearwater Beach. The cheapest flight overall is $39 while the most popular route, (Chicago O'Hare Intl - Tampa) is currently priced at $85.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Clearwater Beach (average of $48). Flying from Chicago to Clearwater Beach in December is currently the most expensive (average of $89). 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 January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$35Average$175FlexibilityNo cancel feeOn-time65%
FrontierCheapest$37Average$185FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$92Average$212FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$401FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$146Average$365FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$151Average$357FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$156Average$341FlexibilityNo cancel feeOn-time71%

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