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$55+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Clearwater are usually found in January or September, booked 61 days in advance, depart on a Wednesday or Thursday and return on a Friday

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 September 15, 2025.

Round-trip from

$99
(Cheapflightsfares)

One-way from

$55
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$188
From Chicago (CHI) to Clearwater
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One-way flight from Chicago (CHI) to Clearwater
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High demand for flights, 0% potential price rise
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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 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 September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/272:25 pmORD - TPA
Nonstop2h 37mMultiple Airlines
Sun 11/911:59 amTPA - ORD
Nonstop3h 00mMultiple Airlines
Deal found 9/14$101
This Cheapflightsfares deal was found by Cheapflights users on 9/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:21 amMDW - TPA
Nonstop2h 36mFrontier
Mon 10/610:52 amTPA - MDW
Nonstop2h 49mFrontier
Deal found 9/12$101
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 12/47:00 amORD - TPA
Nonstop2h 42mMultiple Airlines
Thu 12/49:26 pmTPA - ORD
Nonstop3h 02mMultiple Airlines
Deal found 9/14$102
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Fri 9/266:21 amMDW - TPA
Nonstop2h 36mFrontier
Fri 10/310:55 amTPA - MDW
Nonstop2h 49mFrontier
Deal found 9/14$102
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Sun 10/125:20 amMDW - TPA
Nonstop2h 35mFrontier
Sun 10/199:57 amTPA - MDW
Nonstop2h 47mFrontier
Deal found 9/14$103
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/272:25 pmORD - TPA
Nonstop2h 37mSpirit Airlines
Sat 12/611:37 amTPA - ORD
Nonstop3h 01mSpirit Airlines
Deal found 9/13$104
This CheapOair deal was found by Cheapflights users on 9/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/195:20 amMDW - TPA
Nonstop2h 35mFrontier
Sun 10/269:57 amTPA - MDW
Nonstop2h 47mFrontier
Deal found 9/13$104
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Thu 9/258:05 amORD - TPA
Nonstop3h 00mMultiple Airlines
Tue 9/308:15 amTPA - ORD
Nonstop3h 03mMultiple Airlines
Deal found 9/13$105
This Cheapflightsfares deal was found by Cheapflights users on 9/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/317:50 amMDW - TPA
Nonstop2h 34mFrontier
Sun 11/210:41 pmTPA - MDW
Nonstop2h 49mFrontier
Deal found 9/12$105
This Trip.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/246:18 pmORD - TPA
Nonstop2h 39mSpirit Airlines
Mon 10/2711:44 amTPA - ORD
Nonstop2h 46mSpirit Airlines
Deal found 9/15$106
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Thu 10/28:05 amORD - TPA
Nonstop3h 00mMultiple Airlines
Mon 10/68:13 amTPA - ORD
Nonstop2h 55mMultiple Airlines
Deal found 9/13$107
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Sat 10/116:00 amORD - TPA
1 stop11h 19mFrontier
Sat 10/181:45 pmTPA - ORD
Nonstop3h 00mFrontier
Deal found 9/14$108

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 September 15, 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

MDW - TPA

MDWTPA

Chicago Midway

Sun 10/12

5:20 am-8:55 am

Nonstop2h 35m

Tampa

Wed 10/15

7:30 am-1:38 pm

1 stop7h 08m

$123

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 10/10

9:00 am-3:53 pm

1 stop5h 53m

Tampa

Sun 10/12

9:57 am-11:44 am

Nonstop2h 47m

$123

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Wed 11/12

11:55 am-3:35 pm

Nonstop2h 40m

Tampa

Tue 11/18

12:45 pm-2:45 pm

Nonstop3h 00m

$137

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 12/17

7:10 am-10:45 am

Nonstop2h 35m

Tampa

Mon 12/22

5:55 pm-7:40 pm

Nonstop2h 45m

$147

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 10/8

6:55 am-10:25 am

Nonstop2h 30m

Tampa

Tue 10/14

6:35 pm-10:05 pm

1 stop4h 30m

$147

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Mon 11/3

9:05 am-12:40 pm

Nonstop2h 35m

Tampa

Wed 11/5

4:30 pm-6:15 pm

Nonstop2h 45m

$147

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 11/18

9:05 am-12:40 pm

Nonstop2h 35m

Tampa

Tue 1/13

12:50 pm-6:35 pm

2 stops6h 45m

$152

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 10/8

10:10 am-3:50 pm

1 stop4h 40m

Tampa

Sat 10/18

7:05 am-8:45 am

Nonstop2h 40m

$157

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 1/17

5:35 pm-9:10 pm

Nonstop2h 35m

Tampa

Sat 1/24

4:50 pm-6:40 pm

Nonstop2h 50m

$157

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Wed 12/3

1:45 pm-9:30 pm

1 stop6h 45m

Tampa

Wed 12/10

6:50 am-12:15 pm

1 stop6h 25m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 41 results
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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 September 12, 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 61 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 September 15, 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 September 14, 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 September 15, 2025.

The most flights from CHI to CL9 are scheduled on a Sunday (63 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (43 on average).

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 September 15, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Clearwater to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
8,015 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
5.8
Fair
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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.

  • How long is the flight from Chicago to Clearwater?

    There are many flights that can get you from Chicago to Clearwater in 2h 35m. Fly via Frontier or Southwest to get the fastest option. There are 998 mi between Chicago and Clearwater. Most flights are nonstop.

  • 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 United Airlines ($69), Southwest ($69), and Frontier ($72).

  • 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 (86%), Spirit Airlines (79%) or Southwest (79%) 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 $439, our data indicates the cheapest price to be $47. The most popular route (Chicago O'Hare Intl - Tampa), is priced around $82.

  • 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$202FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$177FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$89Average$185FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$157Average$372FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$160Average$342FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$163Average$374FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$363FlexibilityNo cancel feeOn-timeN/A

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