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$61+ 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 7/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Clearwater Beach are usually found in September or January, booked 75 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

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 July 3, 2025.

Round-trip from

$129
(Frontier)

One-way from

$61
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$209
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. 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 July 2025
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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 July 3, 2025.

This Frontier deal was found by Cheapflights users on 7/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/73:58 pmMDW - TPA
Nonstop2h 41mFrontier
Sun 8/108:32 pmTPA - MDW
Nonstop2h 52mFrontier
Deal found 7/1$129
This Priceline deal was found by Cheapflights users on 7/2. 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.
Sat 8/99:55 amORD - TPA
1 stop7h 09mFrontier
Mon 8/117:26 pmTPA - ORD
1 stop5h 56mFrontier
Deal found 7/2$134
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Fri 8/155:28 pmORD - TPA
Nonstop2h 52mMultiple Airlines
Wed 8/208:28 amTPA - ORD
Nonstop2h 58mMultiple Airlines
Deal found 7/2$137
This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/168:50 amORD - TPA
Nonstop2h 47mSpirit Airlines
Wed 7/231:32 pmTPA - ORD
Nonstop3h 10mSpirit Airlines
Deal found 7/2$142
This American Airlines deal was found by Cheapflights users on 7/3. 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 10/186:10 pmORD - TPA
Nonstop2h 49mAmerican Airlines
Wed 10/297:01 amTPA - ORD
Nonstop3h 03mAmerican Airlines
Deal found 7/3$157
This Southwest deal was found by Cheapflights users on 7/3. 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.
Sat 8/165:30 pmMDW - TPA
Nonstop2h 35mSouthwest
Mon 8/189:05 pmTPA - MDW
Nonstop2h 40mSouthwest
Deal found 7/3$157
This Southwest deal was found by Cheapflights users on 7/3. 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 10/3012:40 pmORD - TPA
1 stop9h 55mSouthwest
Tue 11/1112:45 pmTPA - ORD
Nonstop3h 00mSouthwest
Deal found 7/3$167

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 July 3, 2025.
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

Thu 8/7

3:58 pm-7:39 pm

Nonstop2h 41m

Tampa

Sun 8/10

8:32 pm-10:24 pm

Nonstop2h 52m

$129

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sat 8/9

9:55 am-6:04 pm

1 stop7h 09m

Tampa

Mon 8/11

7:26 pm-12:22 am

1 stop5h 56m

$134

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Fri 8/15

5:28 pm-9:20 pm

Nonstop2h 52m

Tampa

Wed 8/20

8:28 am-10:26 am

Nonstop2h 58m

$137

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Wed 7/16

8:50 am-12:37 pm

Nonstop2h 47m

Tampa

Wed 7/23

1:32 pm-3:42 pm

Nonstop3h 10m

$142

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sat 10/18

6:10 pm-9:59 pm

Nonstop2h 49m

Tampa

Wed 10/29

7:01 am-9:04 am

Nonstop3h 03m

$157

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 8/16

5:30 pm-9:05 pm

Nonstop2h 35m

Tampa

Mon 8/18

9:05 pm-10:45 pm

Nonstop2h 40m

$157

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Thu 10/30

12:40 pm-11:35 pm

1 stop9h 55m

Tampa

Tue 11/11

12:45 pm-2:45 pm

Nonstop3h 00m

$167

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sun 7/27

3:58 pm-7:39 pm

Nonstop2h 41m

$61

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sat 7/12

12:20 pm-4:12 pm

Nonstop2h 52m

$62

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Wed 7/16

8:50 am-12:37 pm

Nonstop2h 47m

$67

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 15 results
1
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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 June 27, 2025.

The best time to book flights from Chicago to Clearwater Beach is 75 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, May is the cheapest month in which you can book a flight from Chicago to Clearwater Beach (average of $206). Flying from Chicago to Clearwater Beach 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 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 July 3, 2025.

When flying from Chicago to Clearwater Beach, 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 Beach?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Clearwater Beach. Price data was last updated on June 29, 2025.

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 July 3, 2025.

The most flights from CHI to CW9 are scheduled on a Thursday (73 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (24 on average).

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 July 3, 2025.
Read through reviews of airlines operating flights from Chicago to Clearwater Beach, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.0

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
4,270 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.0

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.
Delta
8.0
Very good
7,970 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.0

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
8,845 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.0

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
8,094 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.0

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
5.9
Fair
3,284 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.0

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.

  • 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 ($61), Spirit Airlines ($67), and United Airlines ($79).

  • 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 (94%), Azul (89%) and United Airlines (87%).

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

    On average you can expect to pay $488 for a flight from Chicago to Clearwater Beach. The cheapest flight overall is $60 while the most popular route, (Chicago O'Hare Intl - Tampa) is currently priced at $95.

  • 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, May is the cheapest month in which you can book a flight from Chicago to Clearwater Beach (average of $206). Flying from Chicago to Clearwater Beach 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 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$184FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$64Average$177FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$89Average$194FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$158Average$383FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$342FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$179Average$389FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$356FlexibilityNo cancel feeOn-timeN/A

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