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$65+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 Thursday and return on a Friday

Cheap 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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/311:34 pmORD - TPA
Nonstop2h 43mMultiple Airlines
Tue 1/69:25 amTPA - ORD
1 stop24h 06mMultiple Airlines
Deal found 12/17$179
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:26 pmORD - TPA
1 stop24h 42mSpirit Airlines
Wed 1/710:41 amTPA - ORD
Nonstop2h 58mSpirit Airlines
Deal found 12/15$193
This Delta deal was found by Cheapflights users on 12/17. 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 12/315:31 pmORD - TPA
1 stop5h 53mDelta
Tue 1/610:05 amTPA - ORD
1 stop7h 39mDelta
Deal found 12/17$197
This Delta deal was found by Cheapflights users on 12/17. 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 12/313:29 pmMDW - TPA
1 stop5h 10mDelta
Tue 1/64:56 pmTPA - MDW
1 stop6h 11mDelta
Deal found 12/17$197
This American Airlines deal was found by Cheapflights users on 12/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:10 pmORD - TPA
Nonstop2h 46mAmerican Airlines
Wed 1/77:01 amTPA - ORD
Nonstop3h 04mAmerican Airlines
Deal found 12/15$198
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/311:24 pmORD - TPA
1 stop5h 39mUnited Airlines
Wed 1/79:36 amTPA - ORD
Nonstop3h 02mUnited Airlines
Deal found 12/17$199
This Expedia deal was found by Cheapflights users on 12/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/292:57 pmORD - TPA
1 stop8h 33mFrontier
Thu 1/154:51 pmTPA - ORD
Nonstop3h 17mFrontier
Deal found 12/16$202
This Mytrip deal was found by Cheapflights users on 12/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:34 pmORD - TPA
Nonstop2h 43mSpirit Airlines
Tue 1/66:03 pmTPA - ORD
2 stops28h 45mSpirit Airlines
Deal found 12/17$203
This Cheapflightsfares deal was found by Cheapflights users on 12/16. 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 12/205:00 amORD - TPA
1 stop11h 08mSpirit Airlines
Thu 12/2510:41 amTPA - ORD
Nonstop2h 58mSpirit Airlines
Deal found 12/16$204
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/301:14 pmORD - TPA
1 stop8h 49mMultiple Airlines
Wed 1/710:41 amTPA - ORD
Nonstop2h 58mMultiple Airlines
Deal found 12/16$209
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/247:00 amORD - TPA
1 stop27h 35mMultiple Airlines
Tue 1/206:55 pmTPA - ORD
1 stop5h 51mMultiple Airlines
Deal found 12/16$210
This Frontier deal was found by Cheapflights users on 12/16. 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 12/2512:39 pmORD - TPA
1 stop10h 47mFrontier
Thu 1/81:15 pmTPA - ORD
Nonstop3h 13mFrontier
Deal found 12/16$217

Find flight deals from Chicago to Clearwater

Keep the following information in mind while searching for Chicago to Clearwater flight deals. Data was last updated December 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$113
(CheapOair)

One-way from

$65
(Super.com)

Popular in

December

Cheapest in

January

Average price

$307
Provider with most accurate pricing for Chicago (CHI)-Tampa flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Tampa flights.
Search Deals
From Chicago (CHI) to Clearwater
Search Deals
One-way flight from Chicago (CHI) to Clearwater
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

Tue 2/3

5:40 pm-9:15 pm

Nonstop2h 35m

Tampa

Tue 2/17

7:00 pm-10:30 pm

1 stop4h 30m

$161

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sun 2/8

8:45 am-6:40 pm

1 stop8h 55m

Tampa

Fri 2/13

2:35 pm-11:10 pm

1 stop9h 35m

$179

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 1/13

10:15 am-5:45 pm

2 stops6h 30m

Tampa

Tue 1/20

4:25 pm-10:55 pm

2 stops7h 30m

$181

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 1/1

12:25 pm-5:45 pm

1 stop4h 20m

Tampa

Tue 1/6

1:45 pm-8:05 pm

1 stop7h 20m

$184

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sun 1/18

1:25 pm-8:15 pm

1 stop5h 50m

Tampa

Thu 1/22

4:45 pm-6:35 pm

Nonstop2h 50m

$184

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Mon 2/2

5:40 pm-9:15 pm

Nonstop2h 35m

Tampa

Thu 2/5

6:50 am-11:00 am

1 stop5h 10m

$192

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 1/24

12:50 pm-4:25 pm

Nonstop2h 35m

Tampa

Thu 1/29

2:40 pm-7:00 pm

1 stop5h 20m

$196

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 1/17

6:45 am-2:47 pm

1 stop7h 02m

Tampa

Sun 1/18

5:30 am-10:27 am

1 stop5h 57m

$197

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 12/31

3:29 pm-9:39 pm

1 stop5h 10m

Tampa

Tue 1/6

4:56 pm-10:07 pm

1 stop6h 11m

$197

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Wed 12/31

1:24 pm-8:03 pm

1 stop5h 39m

Tampa

Wed 1/7

9:36 am-11:38 am

Nonstop3h 02m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 40 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 December 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 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, March is the cheapest month in which you can book a flight from Chicago to Clearwater (average of $42). Flying from Chicago to Clearwater in December is currently the most expensive (average of $89). 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 December 18, 2025.

It’s typically best to fly out from Chicago to Clearwater in the afternoon. Doing so could potentially save you 22% on the flight price compared to flying in the evening, which is usually more expensive.

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 December 13, 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. Thursday 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 December 18, 2025.

The most flights from CHI to CL9 are scheduled on a Wednesday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

How much does it cost to fly round-trip from Chicago to Clearwater?

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 December 18, 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
7.9
Good
4,250 reviews

Crew

8.6

Food

7.0

Overall

7.9

Comfort

8.0

Boarding

8.1

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
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Crew

8.6

Food

7.0

Overall

7.9

Comfort

8.0

Boarding

8.1

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
9,091 reviews
Southwest
7.9
Good
4,250 reviews

Crew

8.6

Food

7.0

Overall

7.9

Comfort

8.0

Boarding

8.1

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
11,054 reviews
Southwest
7.9
Good
4,250 reviews

Crew

8.6

Food

7.0

Overall

7.9

Comfort

8.0

Boarding

8.1

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
8,190 reviews
Southwest
7.9
Good
4,250 reviews

Crew

8.6

Food

7.0

Overall

7.9

Comfort

8.0

Boarding

8.1

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
3,081 reviews
Southwest
7.9
Good
4,250 reviews

Crew

8.6

Food

7.0

Overall

7.9

Comfort

8.0

Boarding

8.1

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 Southwest, JetBlue, or United Airlines to get the fastest option. There are 998 mi between Chicago and Clearwater. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 Frontier ($37), Spirit Airlines ($43), and Southwest ($68).

  • 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 (88%), Volaris (83%) or Azul (81%) 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 $464, our data indicates the cheapest price to be $48. The most popular route (Chicago O'Hare Intl - Tampa), is priced around $71.

  • 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, March is the cheapest month in which you can book a flight from Chicago to Clearwater (average of $42). Flying from Chicago to Clearwater in December is currently the most expensive (average of $89). 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 8 airlines flying from Chicago to Clearwater

Discover the top 8 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$197FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$180FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$96Average$212FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$146Average$360FlexibilityNo cancel feeOn-time63%
DeltaCheapest$149Average$381FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$156Average$318FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$157Average$370FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$195Average$296FlexibilityNo cancel feeOn-time62%

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