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

The cheapest airlines for a one-way flight from Clearwater to Chicago are Frontier ($48), Southwest ($78), and JetBlue ($88).

Weekly flight availability from Clearwater to Chicago

The most flights from CL9 to CHI are scheduled on a Sunday (75 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the most popular routes from Clearwater to Chicago?

Most travelers choose Tampa - Chicago O'Hare Intl, Tampa - Chicago Midway or Tampa - Chicago Greater Rockford when deciding on the best route from Clearwater to Chicago.

What are the cheapest flights from Clearwater to Chicago?

Looking at all options, your cheapest flight can be booked for $99. While the most popular route (Tampa - Chicago O'Hare Intl) can be booked for $84 on average, our data indicates $741 when flying from Clearwater to Chicago.

What are the most reliable airlines from Clearwater to Chicago?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Clearwater to Chicago on time: Azul (100%), Porter Airlines (100%), Japan Airlines (90%).

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

When booking a flight from Clearwater to Chicago, you may want to consider flying on United Airlines, American Airlines or Southwest as they are the most popular for this route.

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

Yes. In addition to deals on Clearwater to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Clearwater to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Clearwater to Chicago.

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

Yes. Cheapflights offers flight deals from Clearwater to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

Find Cheap Flights from Clearwater to Chicago

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

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Most accurate provider	FlightHub 3 stars
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Popular in	July
Cheapest in	January
Average price	$288

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

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Highest demand for flights based on searches. 15% potential increase in price ($53 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).

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Average for round-trip flights in November 2026

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

Prices

Airlines

What is the cheapest time of day to fly from CL9 to CHI?

When flying from Clearwater to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 24% versus a flight at noon.

What is the cheapest day to fly from Clearwater to Chicago?

Travelers seeking maximum savings on their Clearwater to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Southwest,United Airlines, andJetBlue from Clearwater to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,219 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Southwest

8.0

Very good

4,219 reviews

Southwest

8.0

Very good

4,219 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

United Airlines

7.3

Good

10,462 reviews

Southwest

8.0

Very good

4,219 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

JetBlue

7.1

Good

3,068 reviews

Southwest

8.0

Very good

4,219 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

American Airlines

7.0

Good

12,212 reviews

Southwest

8.0

Very good

4,219 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Frontier

5.5

Fair

2,510 reviews

Southwest

8.0

Very good

4,219 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

What are the cheapest airlines to fly from Clearwater to Chicago one-way?
The cheapest airlines for a one-way flight from Clearwater to Chicago are Frontier ($48), Southwest ($78), and JetBlue ($88).
What are the most popular routes from Clearwater to Chicago?
Most travelers choose Tampa - Chicago O'Hare Intl, Tampa - Chicago Midway or Tampa - Chicago Greater Rockford when deciding on the best route from Clearwater to Chicago.
What are the most reliable airlines from Clearwater to Chicago?
Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Clearwater to Chicago on time: Azul (100%), Porter Airlines (100%), Japan Airlines (90%).
What are the cheapest flights from Clearwater to Chicago?
Looking at all options, your cheapest flight can be booked for $99. While the most popular route (Tampa - Chicago O'Hare Intl) can be booked for $84 on average, our data indicates $741 when flying from Clearwater to Chicago.
Can I find deals for flights from Clearwater to Chicago that include hotel bookings?
Yes. In addition to deals on Clearwater to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Clearwater to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Clearwater to Chicago.
Can I find deals for business class flights from Clearwater to Chicago?
Yes. Cheapflights offers flight deals from Clearwater to Chicago 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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Top 7 airlines flying from Clearwater to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$58	Average$228	FlexibilityNo cancel fee	On-time62%
Allegiant Air	Cheapest$96	Average$200	FlexibilityNo cancel fee	On-time88%
Delta	Cheapest$98	Average$306	FlexibilityNo cancel fee	On-timeN/A
JetBlue	Cheapest$146	Average$329	FlexibilityNo cancel fee	On-time62%
Southwest	Cheapest$157	Average$366	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$177	Average$399	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$179	Average$363	FlexibilityNo cancel fee	On-time71%

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Cheap flights from Clearwater, FL to Chicago (CHI)

Find cheap flights from Clearwater to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Find flight deals from Clearwater to Chicago

Most accurate provider

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Popular in

Cheapest in

Average price

Cheapflights Insights

What is the cheapest time of day to fly from CL9 to CHI?

When flying from Clearwater to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 24% versus a flight at noon.

What is the cheapest day to fly from Clearwater to Chicago?

Travelers seeking maximum savings on their Clearwater to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Clearwater to Chicago

The most flights from CL9 to CHI are scheduled on a Sunday (75 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Southwest,United Airlines, andJetBlue from Clearwater to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

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

What are the most popular routes from Clearwater to Chicago?

What are the most reliable airlines from Clearwater to Chicago?

What are the cheapest flights from Clearwater to Chicago?

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

How can I find direct flights from Clearwater to Chicago?

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

Traveling to a place near Chicago?

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Alternative routes for Clearwater to Chicago

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Other flights to Chicago

Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 3, 2026.

Complete your trip

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Search flights from Clearwater to Chicago by cabin class

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