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Clearwater

$62+ 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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Mar 2 — Mar 91
Mon 3/2
Mon 3/9
1 adult, Economy
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Find cheap flights from Chicago to Clearwater with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Clearwater are usually found in September or October, booked 32 days in advance, depart on a Wednesday or Thursday and return on a Thursday

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 January 31, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/30. 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 3/54:42 pm
ORD
-
TPA
1 stop6h 43m
Frontier
Fri 3/65:30 pm
TPA
-
ORD
Nonstop3h 14m
Frontier
Deal found 1/30$116
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 2/272:13 pm
ORD
-
TPA
Nonstop3h 06m
Multiple Airlines
Fri 3/66:38 pm
TPA
-
ORD
1 stop6h 09m
Multiple Airlines
Deal found 1/30$117
This Frontier deal was found by Cheapflights users on 1/30. 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.
Wed 3/411:51 am
ORD
-
TPA
1 stop9h 38m
Frontier
Mon 3/91:21 pm
TPA
-
ORD
Nonstop3h 14m
Frontier
Deal found 1/30$118
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 5/1910:17 am
ORD
-
TPA
Nonstop2h 47m
Spirit Airlines
Wed 5/273:09 pm
TPA
-
ORD
Nonstop3h 01m
Spirit Airlines
Deal found 1/30$119
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 5/510:17 am
ORD
-
TPA
Nonstop2h 47m
Spirit Airlines
Wed 5/133:09 pm
TPA
-
ORD
Nonstop3h 01m
Spirit Airlines
Deal found 1/28$120
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 3/119:28 am
ORD
-
TPA
1 stop10h 32m
Multiple Airlines
Tue 3/243:11 pm
TPA
-
ORD
Nonstop3h 00m
Multiple Airlines
Deal found 1/29$121
This Expedia deal was found by Cheapflights users on 1/31. 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.
Wed 3/410:19 am
ORD
-
TPA
Nonstop2h 47m
Multiple Airlines
Sun 3/810:15 pm
TPA
-
ORD
Nonstop3h 09m
Multiple Airlines
Deal found 1/31$122
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Sat 2/215:05 am
ORD
-
TPA
1 stop5h 52m
Multiple Airlines
Tue 2/248:30 am
TPA
-
ORD
1 stop11h 41m
Multiple Airlines
Deal found 1/29$123
This Orbitz deal was found by Cheapflights users on 1/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:00 am
ORD
-
TPA
1 stop9h 33m
Multiple Airlines
Mon 3/27:00 am
TPA
-
ORD
1 stop11h 23m
Multiple Airlines
Deal found 1/30$124
This CheapOair deal was found by Cheapflights users on 1/30. 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.
Thu 3/512:15 pm
ORD
-
TPA
Nonstop2h 58m
Multiple Airlines
Tue 3/103:01 pm
TPA
-
ORD
Nonstop3h 02m
Multiple Airlines
Deal found 1/30$125
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Sun 3/158:41 pm
ORD
-
TPA
1 stop9h 38m
Multiple Airlines
Thu 3/199:40 pm
TPA
-
ORD
Nonstop3h 04m
Multiple Airlines
Deal found 1/29$126
This Orbitz deal was found by Cheapflights users on 1/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:19 am
ORD
-
TPA
Nonstop2h 47m
Spirit Airlines
Sat 2/286:38 pm
TPA
-
ORD
1 stop6h 09m
Spirit Airlines
Deal found 1/30$127

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 January 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$115
(Kiwi.com)

One-way from

$62
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$211
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. 14% potential increase in price ($40 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 January 2026
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 January 31, 2026.
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

Sat 2/28

3:55 pm-7:44 pm

Nonstop2h 49m

Tampa

Tue 3/10

2:24 pm-4:33 pm

Nonstop3h 09m

$168

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Tue 2/3

10:07 am-1:54 pm

Nonstop2h 47m

Tampa

Wed 2/4

2:57 pm-4:58 pm

Nonstop3h 01m

$179

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 3/3

5:55 am-1:45 pm

1 stop6h 50m

Tampa

Wed 3/11

7:00 am-8:50 am

Nonstop2h 50m

$187

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 3/3

5:40 pm-9:15 pm

Nonstop2h 35m

Tampa

Tue 3/24

7:00 am-8:50 am

Nonstop2h 50m

$197

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sun 3/1

5:37 pm-11:38 pm

1 stop5h 01m

Tampa

Sat 3/7

8:40 am-2:10 pm

1 stop6h 30m

$198

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sat 2/28

3:55 pm-7:44 pm

Nonstop2h 49m

Tampa

Thu 3/12

7:15 am-9:21 am

Nonstop3h 06m

$208

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Tue 3/17

7:10 am-12:35 pm

1 stop4h 25m

Tampa

Tue 3/24

1:05 pm-4:49 pm

1 stop4h 44m

$217

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Tue 3/17

7:10 am-12:35 pm

1 stop4h 25m

Tampa

Wed 3/25

7:59 pm-11:54 pm

1 stop4h 55m

$217

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Tue 2/24

5:25 am-11:33 am

1 stop5h 08m

Tampa

Tue 2/24

7:57 pm-11:56 pm

1 stop4h 59m

$217

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 2/24

10:49 am-4:50 pm

1 stop5h 01m

Tampa

Wed 2/25

5:25 am-9:54 am

1 stop5h 29m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/31

Showing 1-10 of 46 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 January 30, 2026.

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 $53). 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 January 31, 2026.

It’s typically best to fly out from Chicago to Clearwater in the afternoon. Doing so could potentially save you 18% on the flight price compared to flying at noon, 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 January 24, 2026.

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 January 31, 2026.

The most flights from CHI to CL9 are scheduled on a Saturday (68 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (32 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 January 31, 2026.
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
4,267 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

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
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

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
9,219 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

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.
American Airlines
7.2
Good
11,213 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

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
8,396 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

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
5.7
Fair
3,054 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

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. 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 47m. Fly via United Airlines, Spirit Airlines, or Southwest to get the fastest option. There are 1013 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 ($40), Spirit Airlines ($43), and Southwest ($71).

  • 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 (82%), Copa Airlines (81%) or SWISS (78%) 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 $493, our data indicates the cheapest price to be $39. 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, March is the cheapest month in which you can book a flight from Chicago to Clearwater (average of $53). 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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See prices for flight routes from nearby airports that may be better suited for you.
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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 January 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$35Average$157FlexibilityNo cancel feeOn-time65%
FrontierCheapest$36Average$190FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$82Average$197FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$404FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$151Average$351FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$152Average$348FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$156Average$341FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$196Average$311FlexibilityNo cancel feeOn-time62%

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