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$59+ Cheap flights from Clearwater, FL to Chicago (CHI)

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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Cheapflights Tip: The best prices from Clearwater to Chicago are usually found in January or February, booked 86 days in advance, depart on a Friday or Thursday and return on a Wednesday

Find flight deals from Clearwater to Chicago

Cheapest flights from Clearwater to Chicago
Explore the most affordable flight options available from Clearwater to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/13. 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.
Sat 10/258:19 amTPA - ORD
Nonstop2h 55mMultiple Airlines
Tue 10/2812:37 pmORD - TPA
1 stop5h 50mMultiple Airlines
Deal found 10/13$99
This CheapOair deal was found by Cheapflights users on 10/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/210:41 pmTPA - MDW
Nonstop2h 49mFrontier
Mon 11/36:06 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 10/12$100
This Priceline deal was found by Cheapflights users on 10/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:44 pmTPA - ORD
1 stop6h 43mMultiple Airlines
Sun 11/97:05 amORD - TPA
Nonstop2h 44mMultiple Airlines
Deal found 10/14$100
This Frontier deal was found by Cheapflights users on 10/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:34 pmTPA - MDW
Nonstop2h 48mFrontier
Mon 11/36:06 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 10/14$101
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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.
Thu 10/2311:15 amTPA - ORD
Nonstop3h 00mFrontier
Sun 10/265:50 amORD - TPA
Nonstop2h 55mFrontier
Deal found 10/14$101
This Frontier deal was found by Cheapflights users on 10/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/143:11 pmTPA - MDW
Nonstop2h 46mFrontier
Sun 11/166:06 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 10/12$102
This Frontier deal was found by Cheapflights users on 10/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:36 pmTPA - ORD
1 stop13h 07mFrontier
Sun 11/27:05 amORD - TPA
Nonstop2h 44mFrontier
Deal found 10/12$102
This CheapOair deal was found by Cheapflights users on 10/13. 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.
Fri 11/143:11 pmTPA - MDW
Nonstop2h 46mFrontier
Mon 11/176:06 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 10/13$103
This Frontier deal was found by Cheapflights users on 10/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2311:15 amTPA - ORD
Nonstop3h 00mFrontier
Mon 10/276:00 amORD - TPA
1 stop8h 53mFrontier
Deal found 10/12$103
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/57:50 amTPA - ORD
1 stop8h 49mFrontier
Sun 11/167:05 amORD - TPA
Nonstop2h 44mFrontier
Deal found 10/13$104
This Frontier deal was found by Cheapflights users on 10/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/132:15 pmTPA - MDW
1 stop7h 16mFrontier
Sun 11/166:06 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 10/14$105
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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.
Thu 11/611:59 amTPA - ORD
Nonstop3h 00mFrontier
Thu 11/1311:50 amORD - TPA
1 stop25h 21mFrontier
Deal found 10/14$105

Cheap flight deals from Clearwater to Chicago

Keep the following information in mind while searching for Clearwater to Chicago flight deals. Data was last updated October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$99
(Kiwi.com)

One-way from

$59
(Frontier)

Popular in

June

Cheapest in

January

Average price

$228
Provider with most accurate pricing for Tampa-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Tampa-Chicago (CHI) flights.
Search Deals
From Clearwater to Chicago (CHI)
Search Deals
One-way flight from Clearwater to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Clearwater to Chicago 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 October 14, 2025.
Use the filters below to find and compare flights from Clearwater to Chicago that are best for you.

Fly from

Clearwater

Fly to

Chicago

Route

Depart

Return

Price

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 11/19

7:30 am-9:30 am

Nonstop3h 00m

Chicago O'Hare Intl

Wed 11/19

11:15 am-3:08 pm

Nonstop2h 53m

$152

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 11/5

12:45 pm-2:45 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sun 11/16

11:55 am-3:35 pm

Nonstop2h 40m

$158

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 11/15

7:40 am-9:39 am

Nonstop2h 59m

Chicago O'Hare Intl

Sun 11/16

7:30 am-11:20 am

Nonstop2h 50m

$158

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 11/14

9:30 pm-11:10 pm

Nonstop2h 40m

Chicago Midway

Sun 11/16

5:20 am-8:55 am

Nonstop2h 35m

$159

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 11/8

7:40 am-9:39 am

Nonstop2h 59m

Chicago O'Hare Intl

Mon 11/10

3:37 pm-7:29 pm

Nonstop2h 52m

$168

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 11/13

9:30 pm-11:10 pm

Nonstop2h 40m

Chicago Midway

Fri 11/14

5:20 am-8:55 am

Nonstop2h 35m

$187

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 11/15

4:55 pm-6:40 pm

Nonstop2h 45m

Chicago Midway

Sun 11/16

5:20 am-8:55 am

Nonstop2h 35m

$188

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 12/3

7:06 pm-11:49 pm

1 stop5h 43m

Chicago Midway

Mon 12/8

10:49 am-5:00 pm

1 stop5h 11m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 1/24

5:55 am-9:56 am

1 stop5h 01m

Chicago Midway

Mon 1/26

10:35 am-4:48 pm

1 stop5h 13m

$197

TampaChicago

TPA - ORD

TPAORD

Tampa

Tue 12/23

8:25 pm-12:02 am

1 stop4h 37m

Chicago O'Hare Intl

Thu 1/1

5:30 pm-12:25 am

1 stop5h 55m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 54 results
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Best time to book a flight from Clearwater to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Clearwater 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 Clearwater to Chicago

How far ahead should I book a flight from Clearwater to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Clearwater to Chicago. Price data was last updated on October 10, 2025.

To ensure you get the cheapest price possible for a flight from Clearwater to Chicago, you should look to book at least 86 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Clearwater to Chicago?

Currently, January is the cheapest month in which you can book a flight from Clearwater to Chicago (average of $31). Flying from Clearwater to Chicago in June is currently the most expensive (average of $107). 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 CL9 to CHI?

Find hourly flight availability from Clearwater to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 14, 2025.

When flying from Clearwater to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 32% versus a flight at noon.

What is the cheapest day to fly from Clearwater to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Clearwater to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Clearwater to Chicago flight should consider departing on Sunday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Clearwater to Chicago

Explore weekly flight availability from Clearwater to Chicago. 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 October 14, 2025.

The most flights from CL9 to CHI are scheduled on a Monday (70 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (46 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated October 14, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Clearwater to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
United Airlines
7.4
Good
8,976 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
11,042 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Spirit Airlines
6.3
Okay
8,096 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.8
Fair
3,135 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Clearwater to Chicago. 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 Clearwater to Chicago?

    For as low as $152, United Airlines can have you in Chicago from Clearwater in 3h. There are 1013 mi between Clearwater and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Clearwater to Chicago?

    Most travelers choose Tampa - Chicago O'Hare Intl, Tampa - Chicago Midway or Tampa - Chicago Greater Rockford when deciding on the best route from Clearwater to Chicago.

  • What are the most reliable airlines from Clearwater to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Clearwater to Chicago on time: ITA Airways (97%), ANA (86%), SWISS (86%).

  • What are the cheapest flights from Clearwater to Chicago?

    Looking at all options, your cheapest flight can be booked for $49. While the most popular route (Tampa - Chicago O'Hare Intl) can be booked for $89 on average, our data indicates $761 when flying from Clearwater to Chicago.

  • Can I find deals for flights from Clearwater to Chicago that include hotel bookings?

    Yes. In addition to deals on Clearwater to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Clearwater to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Clearwater to Chicago.

  • Can I find deals for business class flights from Clearwater to Chicago?

    Yes. Cheapflights offers flight deals from Clearwater to Chicago 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 Clearwater to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Clearwater to Chicago (average of $31). Flying from Clearwater to Chicago in June is currently the most expensive (average of $107). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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Alternative routes for Clearwater to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Clearwater to Chicago

Discover the top 7 airlines that operate flights from Clearwater to Chicago. 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$160FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$60Average$161FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$74Average$144FlexibilityNo cancel feeOn-time65%
DeltaCheapest$98Average$408FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$143Average$308FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$352FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$315FlexibilityNo cancel feeOn-time71%

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