HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Clearwater

$53+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Clearwater with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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

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 November 2, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/42:18 pmORD - TPA
Nonstop3h 12mFrontier
Wed 12/105:45 amTPA - ORD
1 stop9h 46mFrontier
Deal found 10/31$106
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/174:01 pmORD - TPA
1 stop6h 28mFrontier
Sun 1/114:36 pmTPA - ORD
Nonstop3h 22mFrontier
Deal found 10/31$107
This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/233:37 pmORD - TPA
Nonstop2h 48mFrontier
Thu 11/278:35 pmTPA - ORD
Nonstop3h 01mFrontier
Deal found 11/2$108
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:00 amORD - TPA
1 stop10h 37mFrontier
Mon 11/172:00 pmTPA - ORD
1 stop10h 44mFrontier
Deal found 11/1$110
This Frontier deal was found by Cheapflights users on 11/1. 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.
Mon 11/176:30 amMDW - TPA
1 stop7h 14mFrontier
Wed 11/198:25 amTPA - MDW
1 stop5h 16mFrontier
Deal found 11/1$110
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/41:34 pmORD - TPA
Nonstop2h 43mSpirit Airlines
Mon 12/810:41 amTPA - ORD
Nonstop2h 58mSpirit Airlines
Deal found 11/2$111
This CheapOair deal was found by Cheapflights users on 10/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/101:34 pmORD - TPA
Nonstop2h 43mSpirit Airlines
Thu 12/1110:41 amTPA - ORD
Nonstop2h 58mSpirit Airlines
Deal found 10/31$112
This Priceline deal was found by Cheapflights users on 10/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/166:06 pmMDW - TPA
Nonstop2h 35mFrontier
Wed 11/198:25 amTPA - MDW
1 stop5h 16mFrontier
Deal found 10/31$112
This Priceline deal was found by Cheapflights users on 11/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:11 amORD - TPA
1 stop6h 11mMultiple Airlines
Wed 12/1010:41 amTPA - ORD
Nonstop2h 58mMultiple Airlines
Deal found 11/1$113
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Thu 11/273:37 pmORD - TPA
Nonstop2h 48mMultiple Airlines
Tue 12/28:12 amTPA - ORD
1 stop11h 34mMultiple Airlines
Deal found 11/2$114
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/167:05 amORD - TPA
Nonstop2h 44mFrontier
Tue 11/187:50 amTPA - ORD
1 stop12h 48mFrontier
Deal found 11/2$115
This CheapOair deal was found by Cheapflights users on 11/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/151:37 pmMDW - TPA
1 stop8h 06mFrontier
Mon 11/1710:41 pmTPA - MDW
Nonstop2h 49mFrontier
Deal found 11/1$115

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 November 2, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$106
(Cheapflightsfares)

One-way from

$53
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$264
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. 0% potential increase in price ($0 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 2, 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 12/2

2:55 pm-6:30 pm

Nonstop2h 35m

Tampa

Tue 12/9

7:15 pm-9:00 pm

Nonstop2h 45m

$158

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 2/21

6:15 pm-9:55 pm

Nonstop2h 40m

Tampa

Wed 2/25

6:05 pm-10:55 pm

1 stop5h 50m

$167

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 3/3

9:55 am-5:45 pm

1 stop6h 50m

Tampa

Wed 3/4

1:45 pm-8:05 pm

1 stop7h 20m

$177

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sat 2/21

3:05 pm-10:15 pm

1 stop6h 10m

Tampa

Wed 2/25

8:25 am-12:15 pm

1 stop4h 50m

$177

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Thu 11/20

12:32 pm-4:13 pm

Nonstop2h 41m

Tampa

Mon 11/24

11:20 am-1:23 pm

Nonstop3h 03m

$184

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 1/17

6:45 am-2:49 pm

1 stop7h 04m

Tampa

Sun 1/18

11:45 am-5:34 pm

1 stop6h 49m

$197

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Sat 1/17

8:00 am-2:49 pm

1 stop5h 49m

Tampa

Sun 1/18

8:30 am-1:07 pm

1 stop5h 37m

$197

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 12/12

7:10 pm-10:45 pm

Nonstop2h 35m

Tampa

Mon 12/15

6:55 pm-10:35 pm

1 stop4h 40m

$207

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 12/11

5:13 pm-12:19 am

1 stop6h 06m

Tampa

Mon 12/15

5:45 am-12:34 pm

1 stop7h 49m

$217

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 12/12

12:50 pm-7:03 pm

1 stop5h 13m

Tampa

Mon 12/15

5:30 am-9:54 am

1 stop5h 24m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 43 results
1
2
3
...
5

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 October 24, 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, January is the cheapest month in which you can book a flight from Chicago to Clearwater (average of $42). Flying from Chicago to Clearwater in October is currently the most expensive (average of $83). 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 November 2, 2025.

It’s typically best to fly out from Chicago to Clearwater in the afternoon. Doing so could potentially save you 29% 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 November 2, 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. Saturday evenings 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 November 2, 2025.

The most flights from CHI to CL9 are scheduled on a Sunday (69 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 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 November 2, 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
4,240 reviews

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

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
8,997 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

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
11,034 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

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
8,120 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

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
3,118 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

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 Southwest, Spirit Airlines, or Delta 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 ($61), Southwest ($79), and United Airlines ($79).

  • 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 Spirit Airlines (92%), ITA Airways (91%) or Copa Airlines (89%) 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 $40. The most popular route (Chicago O'Hare Intl - Tampa), is priced around $76.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Clearwater (average of $42). Flying from Chicago to Clearwater in October is currently the most expensive (average of $83). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Clearwater

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Fort Myers flights
Midway to Orlando flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Sarasota flights
Midway to Miami flights
Midway to Tampa flights
Midway to Fort Lauderdale flights
Midway to Fort Myers flights
St. Louis to Orlando flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Key West flights
O'Hare Intl to Pensacola flights
St. Louis to Miami flights
Midway to West Palm Beach flights
St. Louis to Fort Lauderdale flights
O'Hare Intl to Panama City flights
Midway to Sarasota flights
St. Louis to Tampa flights
Moline to Orlando flights
Rockford to Orlando Sanford Intl flights
Midway to Jacksonville flights
St. Louis to Fort Myers flights
Midway to Key West flights
St. Louis to Key West flights
Peoria to Orlando flights
Midway to Pensacola flights
O'Hare Intl to Daytona Beach flights
Rockford to St Petersburg flights
Moline to Tampa flights
Rockford to Punta Gorda flights
St. Louis to Sarasota flights
O'Hare Intl to Valparaiso flights
Peoria to Miami flights
St. Louis to Jacksonville flights
Peoria to Fort Lauderdale flights
St. Louis to Pensacola flights
Moline to Fort Myers flights
Moline to Fort Lauderdale flights
Midway to Panama City flights
Springfield to Orlando flights
Moline to Sarasota flights
Peoria to Fort Myers flights
O'Hare Intl to Melbourne flights
Midway to Valparaiso flights
O'Hare Intl to St Petersburg flights
Midway to Daytona Beach flights

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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$207FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$177FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$93Average$193FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$156Average$331FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$364FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$157Average$369FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$379FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.