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$43+ 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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Chicago to Clearwater are usually found in September or January, booked 75 days in advance, depart on a Tuesday or Wednesday 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$87
(Cheapflightsfares)

One-way from

$43
(Booking.com)

Popular in

March

Cheapest in

September

Average price

$229
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
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One-way flight from Chicago (CHI) to Clearwater
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Highest demand for flights based on searches. 5% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 3/57:25 amORD - TPA
Nonstop2h 48mFrontier
Wed 3/128:50 amTPA - ORD
Nonstop3h 07mFrontier
Deal found 2/20$87
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Mon 3/315:01 amORD - TPA
Nonstop2h 48mMultiple Airlines
Mon 4/75:00 amTPA - ORD
Nonstop3h 04mMultiple Airlines
Deal found 2/20$88
This Trip.com deal was found by Cheapflights users on 2/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/123:14 pmMDW - TPA
Nonstop2h 41mFrontier
Wed 3/267:55 pmTPA - MDW
Nonstop2h 56mFrontier
Deal found 2/20$89
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 3/2511:04 amORD - TPA
Nonstop2h 46mSpirit Airlines
Tue 4/83:55 pmTPA - ORD
Nonstop3h 10mSpirit Airlines
Deal found 2/20$90
This JetBlue deal was found by Cheapflights users on 2/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/301:24 pmORD - TPA
1 stop8h 46mJetBlue
Wed 4/910:30 amTPA - ORD
1 stop8h 37mJetBlue
Deal found 2/20$197
This Delta deal was found by Cheapflights users on 2/20. 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 3/265:00 pmORD - TPA
1 stop5h 09mDelta
Wed 4/92:21 pmTPA - ORD
1 stop4h 58mDelta
Deal found 2/20$209
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/16:00 amMDW - TPA
1 stop5h 28mDelta
Tue 4/156:00 amTPA - MDW
1 stop4h 07mDelta
Deal found 2/19$209
This Southwest deal was found by Cheapflights users on 2/19. 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 3/182:40 pmMDW - TPA
Nonstop2h 35mSouthwest
Tue 3/258:30 amTPA - MDW
Nonstop2h 45mSouthwest
Deal found 2/19$213

Find flights from Chicago to Clearwater within your budget

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 February 20, 2025.

Fly from

Chicago

Fly to

Clearwater

Route

Depart

Return

Price

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Wed 3/5

7:25 am-11:13 am

Nonstop2h 48m

Tampa

Wed 3/12

8:50 am-10:57 am

Nonstop3h 07m

$87

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Mon 3/31

5:01 am-8:49 am

Nonstop2h 48m

Tampa

Thu 4/10

9:26 pm-11:22 pm

Nonstop2h 56m

$88

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 3/12

3:14 pm-6:55 pm

Nonstop2h 41m

Tampa

Wed 3/26

7:55 pm-9:51 pm

Nonstop2h 56m

$89

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Tue 3/25

11:04 am-2:50 pm

Nonstop2h 46m

Tampa

Tue 4/8

3:55 pm-6:05 pm

Nonstop3h 10m

$90

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sun 3/30

1:24 pm-11:10 pm

1 stop8h 46m

Tampa

Wed 4/9

10:30 am-6:07 pm

1 stop8h 37m

$197

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Wed 3/26

5:00 pm-11:09 pm

1 stop5h 09m

Tampa

Wed 4/9

2:21 pm-6:19 pm

1 stop4h 58m

$209

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 4/1

6:00 am-12:28 pm

1 stop5h 28m

Tampa

Tue 4/15

6:00 am-9:07 am

1 stop4h 07m

$209

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 3/18

2:40 pm-6:15 pm

Nonstop2h 35m

Tampa

Tue 3/25

8:30 am-10:15 am

Nonstop2h 45m

$213

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sun 4/6

8:10 pm-11:59 pm

Nonstop2h 49m

$43

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 4/11

8:56 am-12:41 pm

Nonstop2h 45m

$45

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 20 results
1
2

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.

Travel insights for flights from Chicago to Clearwater

Get recent, data-driven insights about flights from Chicago to Clearwater including ideal travel times, pricing trends, and more.

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 February 14, 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 75 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 February 20, 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 February 16, 2025.

Travelers seeking maximum savings on their Chicago to Clearwater 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

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 February 20, 2025.

The most flights from CHI to CL9 are scheduled on a Thursday (63 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 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 February 20, 2025.
Read reviews from past customers who have flown Southwest, Delta and JetBlue from Chicago to Clearwater. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

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
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

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
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

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
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

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
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

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
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

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 ($43), Frontier ($43), and Southwest ($95).

  • 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 Azul (87%), Copa Airlines (84%) or Air Canada (83%) 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 $628, our data indicates the cheapest price to be $46. The most popular route (Chicago O'Hare Intl - Tampa), is priced around $56.

  • 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$175FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$161FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$97Average$208FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$128Average$352FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$155Average$328FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$178Average$408FlexibilityNo cancel feeOn-time63%
DeltaCheapest$195Average$375FlexibilityNo cancel feeOn-timeN/A
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