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$67+ Cheap flights from Chicago (CHI) to Clearwater, 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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Clearwater are usually found in January or September, booked 32 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap flight deals from Chicago to Clearwater

Keep the following information in mind while searching for Chicago to Clearwater flight deals. Data was last updated June 12, 2025.

Round-trip from

$123
(Cheapflightsfares)

One-way from

$67
(FlightHub)

Popular in

March

Cheapest in

January

Average price

$263
From Chicago (CHI) to Clearwater
Search Deals
One-way flight from Chicago (CHI) to Clearwater
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($4 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 June 2025
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Find flight deals from Chicago to Clearwater

Cheapest flights from Chicago to Clearwater
Explore the most affordable flight options available from Chicago to Clearwater. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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 7/98:50 amORD - TPA
Nonstop2h 47mSpirit Airlines
Wed 7/301:32 pmTPA - ORD
Nonstop3h 10mSpirit Airlines
Deal found 6/10$123
This SmartFares deal was found by Cheapflights users on 6/12. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/45:30 pmORD - TPA
Nonstop2h 52mFrontier
Mon 8/1810:17 pmTPA - ORD
Nonstop3h 08mFrontier
Deal found 6/12$124
This Priceline deal was found by Cheapflights users on 6/11. 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.
Mon 9/156:21 amMDW - TPA
Nonstop2h 39mFrontier
Mon 9/2210:55 amTPA - MDW
Nonstop2h 49mFrontier
Deal found 6/11$128
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 7/17:27 amORD - TPA
Nonstop2h 44mMultiple Airlines
Mon 7/710:17 pmTPA - ORD
Nonstop3h 08mMultiple Airlines
Deal found 6/10$145
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/306:10 pmORD - TPA
Nonstop2h 50mAmerican Airlines
Mon 9/17:00 amTPA - ORD
Nonstop3h 06mAmerican Airlines
Deal found 6/11$157
This Southwest deal was found by Cheapflights users on 6/10. 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 8/78:05 pmMDW - TPA
Nonstop2h 35mSouthwest
Mon 8/116:55 amTPA - MDW
Nonstop2h 40mSouthwest
Deal found 6/10$157
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/75:45 pmORD - TPA
1 stop5h 25mSouthwest
Mon 8/115:40 amTPA - ORD
1 stop6h 05mSouthwest
Deal found 6/12$177
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1711:12 amORD - TPA
Nonstop2h 50mUnited Airlines
Wed 8/67:30 amTPA - ORD
Nonstop3h 04mUnited Airlines
Deal found 6/10$187
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 7/125:20 pmORD - TPA
1 stop5h 09mDelta
Wed 7/166:00 amTPA - ORD
1 stop5h 16mDelta
Deal found 6/11$197
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 7/264:22 pmMDW - TPA
1 stop6h 52mDelta
Tue 7/297:50 amTPA - MDW
1 stop5h 08mDelta
Deal found 6/11$197
This Sun Country Air deal was found by Cheapflights users on 6/10. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/146:21 pmORD - TPA
1 stop15h 29mSun Country Air
Mon 7/2111:47 amTPA - ORD
1 stop6h 40mSun Country Air
Deal found 6/10$275

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Clearwater 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 June 12, 2025.
Use the filters below to find and compare flights from Chicago to Clearwater that are best for you.

Fly from

Chicago

Fly to

Clearwater

Route

Depart

Return

Price

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Wed 7/9

8:50 am-12:37 pm

Nonstop2h 47m

Tampa

Wed 7/30

1:32 pm-3:42 pm

Nonstop3h 10m

$123

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Mon 8/4

5:30 pm-9:22 pm

Nonstop2h 52m

Tampa

Mon 8/18

10:17 pm-12:25 am

Nonstop3h 08m

$124

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Tue 7/1

7:27 am-11:11 am

Nonstop2h 44m

Tampa

Mon 7/7

10:17 pm-12:25 am

Nonstop3h 08m

$145

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 8/12

11:39 am-11:05 pm

1 stop10h 26m

Tampa

Thu 8/14

8:32 pm-10:24 pm

Nonstop2h 52m

$151

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sat 8/30

6:10 pm-10:00 pm

Nonstop2h 50m

Tampa

Mon 9/1

7:00 am-9:06 am

Nonstop3h 06m

$157

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 8/7

8:05 pm-11:40 pm

Nonstop2h 35m

Tampa

Mon 8/11

6:55 am-8:35 am

Nonstop2h 40m

$157

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Thu 8/7

5:45 pm-12:10 am

1 stop5h 25m

Tampa

Mon 8/11

5:40 am-10:45 am

1 stop6h 05m

$177

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Thu 7/17

11:12 am-3:02 pm

Nonstop2h 50m

Tampa

Wed 8/6

7:30 am-9:34 am

Nonstop3h 04m

$187

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sat 7/12

5:20 pm-11:29 pm

1 stop5h 09m

Tampa

Wed 7/16

6:00 am-10:16 am

1 stop5h 16m

$197

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 7/19

4:22 pm-11:19 pm

1 stop5h 57m

Tampa

Sat 7/26

5:20 am-9:45 am

1 stop5h 25m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 24 results
1
2
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Best time to book a flight from Chicago to Clearwater

Have a flexible travel schedule? Discover the best time to fly to Clearwater 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

How far ahead should I book a flight from Chicago to Clearwater?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Clearwater. Price data was last updated on June 9, 2025.

The price you pay for your flight from Chicago to Clearwater may vary depending on when you book. For the best chance of a lower fare, look to book 32 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Clearwater?

Currently, May is the cheapest month in which you can book a flight from Chicago to Clearwater (average of $206). Flying from Chicago to Clearwater 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 CL9?

Find hourly flight availability from Chicago to Clearwater. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.

When flying from Chicago to Clearwater, 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?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Clearwater. Price data was last updated on June 8, 2025.

Travelers seeking maximum savings on their Chicago to Clearwater 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

Explore weekly flight availability from Chicago to Clearwater. 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 June 12, 2025.

The most flights from CHI to CL9 are scheduled on a Thursday (72 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 on average).

Rainfall in Clearwater by month

Plan your trip to Clearwater by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Clearwater 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 when rainfall is around 1.6 in.

Temperature in Clearwater by month

Plan your trip to Clearwater by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Clearwater, 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

Get insights into the airlines that provide service to Clearwater. 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. Reviews last updated June 12, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Chicago to Clearwater. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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.
JetBlue
7.3
Good
2,925 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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. 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 one-way?

    The cheapest airlines for a one-way flight from Chicago to Clearwater are Spirit Airlines ($67), United Airlines ($79), and Southwest ($79).

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

    No one likes to see their flight delayed. When booking a flight from Chicago to Clearwater consider choosing Copa Airlines (92%), United Airlines (89%) or Azul (88%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Clearwater?

    Looking for the cheapest flight from Chicago to Clearwater? While on average our users pay $538, our data indicates the cheapest price to be $49. The most popular route (Chicago O'Hare Intl - Tampa), is priced around $123.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Clearwater 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?

    Currently, May is the cheapest month in which you can book a flight from Chicago to Clearwater (average of $206). Flying from Chicago to Clearwater 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

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Top 7 airlines flying from Chicago to Clearwater

Discover the top 7 airlines that operate flights from Chicago to Clearwater. 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$178FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$64Average$177FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$88Average$193FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$155Average$382FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$341FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$181Average$396FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$374FlexibilityNo cancel feeOn-timeN/A

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