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 ($43), Southwest ($82), and American Airlines ($83).

Weekly flight availability from Chicago to Clearwater Beach

The most flights from CHI to CW9 are scheduled on a Tuesday (66 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (18 on average).

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.

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).

What are the cheapest flights from Chicago to Clearwater Beach?

On average you can expect to pay $496 for a flight from Chicago to Clearwater Beach. The cheapest flight overall is $88 while the most popular route, (Chicago O'Hare Intl - Tampa) is currently priced at $172.

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 Sun Country Air (100%), Copa Airlines (87%) and Azul (80%).

What are the most popular airlines that fly from Chicago to Clearwater Beach?

Before booking your flight from Chicago to Clearwater Beach check out the most popular airlines for this route: United Airlines, American Airlines or Frontier.

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.

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Cheapflights Tip: The best prices from Chicago to Clearwater Beach are usually found in January or October, booked 89 days in advance, depart on a Wednesday or Saturday and return on a Thursday

Find flight deals from Chicago to Clearwater Beach

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Popular in	June
Cheapest in	January
Average price	$320

Provider with most accurate pricing for Chicago (CHI)-Tampa flight deals.

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Highest demand for flights based on searches. 9% potential increase in price ($31 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 2026

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Everything you need to know about your flight from Chicago to Clearwater Beach

Prices

Airlines

What is the cheapest time of day to fly from CHI to CW9?

Unlike in the evening, when flights are generally more expensive, you can save up to 16% 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?

Travelers seeking maximum savings on their Chicago to Clearwater Beach flight should consider departing on Wednesday afternoons 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.

Reviews of airlines servicing Clearwater Beach

Read through reviews of airlines operating flights from Chicago to Clearwater Beach, such as Southwest,United Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,196 reviews

Reviews

1 / 20

6.0

Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Southwest

8.0

Very good

4,196 reviews

Southwest

8.0

Very good

4,196 reviews

Reviews

1 / 20

6.0

Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

United Airlines

7.4

Good

10,228 reviews

Southwest

8.0

Very good

4,196 reviews

Reviews

1 / 20

6.0

Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

JetBlue

7.1

Good

3,037 reviews

Southwest

8.0

Very good

4,196 reviews

Reviews

1 / 20

6.0

Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

American Airlines

7.0

Good

12,075 reviews

Southwest

8.0

Very good

4,196 reviews

Reviews

1 / 20

6.0

Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Frontier

5.6

Fair

2,579 reviews

Southwest

8.0

Very good

4,196 reviews

Reviews

1 / 20

6.0

Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Related info for your journey

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 ($43), Southwest ($82), and American Airlines ($83).
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 Sun Country Air (100%), Copa Airlines (87%) and Azul (80%).
What are the cheapest flights from Chicago to Clearwater Beach?
On average you can expect to pay $496 for a flight from Chicago to Clearwater Beach. The cheapest flight overall is $88 while the most popular route, (Chicago O'Hare Intl - Tampa) is currently priced at $172.
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.

See more FAQs

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Top 7 airlines flying from Chicago to Clearwater Beach

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$48	Average$234	FlexibilityNo cancel fee	On-time62%
Allegiant Air	Cheapest$87	Average$220	FlexibilityNo cancel fee	On-time88%
Delta	Cheapest$109	Average$329	FlexibilityNo cancel fee	On-timeN/A
JetBlue	Cheapest$147	Average$288	FlexibilityNo cancel fee	On-time62%
American Airlines	Cheapest$156	Average$377	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$166	Average$374	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$168	Average$371	FlexibilityNo cancel fee	On-time63%

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Cheap flights from Chicago (CHI) to Clearwater Beach, FL

Find cheap flights from Chicago to Clearwater Beach with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Find flight deals from Chicago to Clearwater Beach

Most accurate provider

Most trusted provider

Popular in

Cheapest in

Average price

Cheapflights Insights

What is the cheapest time of day to fly from CHI to CW9?

Unlike in the evening, when flights are generally more expensive, you can save up to 16% 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?

Travelers seeking maximum savings on their Chicago to Clearwater Beach flight should consider departing on Wednesday afternoons 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

The most flights from CHI to CW9 are scheduled on a Tuesday (66 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (18 on average).

Reviews of airlines servicing Clearwater Beach

Read through reviews of airlines operating flights from Chicago to Clearwater Beach, such as Southwest,United Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

What are the cheapest airlines to fly from Chicago to Clearwater Beach one-way?

What are the most reliable airlines from Chicago to Clearwater Beach?

What are the cheapest flights from Chicago to Clearwater Beach?

Can I find deals for flights from Chicago to Clearwater Beach that include hotel bookings?

How can I find direct flights from Chicago to Clearwater Beach?

Can I find deals for business class flights from Chicago to Clearwater Beach?

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.

Complete your trip

Complete your trip to Clearwater Beach by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Chicago to Clearwater Beach by cabin class

Find flights from Chicago to Clearwater Beach, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Chicago and Clearwater Beach flights

Browse other Chicago and Clearwater Beach flight options. Last updated on September 23, 2026.

Other flights from Chicago

Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 23, 2026.

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Top 7 airlines flying from Chicago to Clearwater Beach

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