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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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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

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 September 11, 2025.

Round-trip from

$100
(CheapOair)

One-way from

$59
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$171
From Clearwater to Chicago (CHI)
Search Deals
One-way flight from Clearwater to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 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 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 September 11, 2025.

This CheapOair deal was found by Cheapflights users on 9/10. 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.
Mon 10/208:13 amTPA - ORD
Nonstop2h 55mSpirit Airlines
Sun 10/266:05 pmORD - TPA
Nonstop2h 38mSpirit Airlines
Deal found 9/10$100
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 9/278:14 amTPA - ORD
Nonstop3h 03mMultiple Airlines
Sun 10/125:50 amORD - TPA
Nonstop2h 55mMultiple Airlines
Deal found 9/10$101
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 10/910:45 amTPA - ORD
Nonstop3h 00mFrontier
Sun 10/125:50 amORD - TPA
Nonstop2h 55mFrontier
Deal found 9/10$102
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 10/310:55 amTPA - MDW
Nonstop2h 49mFrontier
Sun 10/56:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 9/11$103
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 10/306:10 amTPA - ORD
1 stop5h 31mFrontier
Sun 11/27:05 amORD - TPA
Nonstop2h 44mFrontier
Deal found 9/10$103
This CheapOair deal was found by Cheapflights users on 9/9. 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 10/242:22 pmTPA - MDW
Nonstop2h 47mFrontier
Sun 10/265:20 amMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/9$104
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/18:15 amTPA - ORD
Nonstop3h 03mSpirit Airlines
Thu 10/166:18 pmORD - TPA
Nonstop2h 39mSpirit Airlines
Deal found 9/10$104
This Frontier deal was found by Cheapflights users on 9/9. 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 10/310:55 amTPA - MDW
Nonstop2h 49mFrontier
Mon 10/66:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 9/9$105
This CheapOair deal was found by Cheapflights users on 9/10. 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 10/25:01 amTPA - ORD
Nonstop3h 09mFrontier
Thu 10/162:41 pmORD - TPA
1 stop9h 03mFrontier
Deal found 9/10$105
This Gotogate deal was found by Cheapflights users on 9/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/25:01 amTPA - ORD
Nonstop3h 09mFrontier
Sun 10/55:35 amORD - TPA
1 stop22h 56mFrontier
Deal found 9/10$106
This Trip.com deal was found by Cheapflights users on 9/8. 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.
Sun 9/2810:55 amTPA - MDW
Nonstop2h 49mFrontier
Sun 10/56:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 9/8$110
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 10/25:01 amTPA - ORD
Nonstop3h 09mFrontier
Tue 10/711:00 amORD - TPA
1 stop7h 32mFrontier
Deal found 9/11$111

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 September 11, 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

Thu 10/2

6:00 am-10:31 am

1 stop5h 31m

Chicago O'Hare Intl

Sun 10/5

8:05 am-12:05 pm

Nonstop3h 00m

$111

TampaChicago

TPA - ORD

TPAORD

Tampa

Fri 10/3

4:53 pm-11:39 pm

1 stop7h 46m

Chicago O'Hare Intl

Sun 10/5

8:05 am-12:05 pm

Nonstop3h 00m

$111

TampaChicago

TPA - ORD

TPAORD

Tampa

Fri 10/3

8:15 am-10:18 am

Nonstop3h 03m

Chicago O'Hare Intl

Sun 10/5

8:05 am-12:05 pm

Nonstop3h 00m

$135

TampaChicago

TPA - ORD

TPAORD

Tampa

Fri 10/24

6:28 am-10:50 am

1 stop5h 22m

Chicago O'Hare Intl

Mon 10/27

2:25 pm-6:02 pm

Nonstop2h 37m

$137

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 10/24

8:10 pm-9:50 pm

Nonstop2h 40m

Chicago Midway

Tue 10/28

6:55 am-10:25 am

Nonstop2h 30m

$140

TampaChicago

TPA - ORD

TPAORD

Tampa

Fri 9/26

4:53 pm-12:10 am

1 stop8h 17m

Chicago O'Hare Intl

Mon 9/29

7:40 am-9:47 pm

1 stop13h 07m

$141

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 11/27

6:00 am-7:45 am

Nonstop2h 45m

Chicago Midway

Tue 12/2

6:00 pm-9:35 pm

Nonstop2h 35m

$147

TampaChicago

TPA - MDW

TPAMDW

Tampa

Mon 11/3

7:15 pm-9:00 pm

Nonstop2h 45m

Chicago Midway

Tue 11/4

6:00 pm-9:35 pm

Nonstop2h 35m

$149

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 10/23

6:50 am-8:30 am

Nonstop2h 40m

Chicago Midway

Sun 10/26

6:55 am-10:25 am

Nonstop2h 30m

$153

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 10/2

6:00 am-3:58 pm

1 stop10h 58m

Chicago Midway

Mon 10/6

5:33 pm-11:29 pm

1 stop4h 56m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 52 results
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2
3
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6

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 August 29, 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, August is the cheapest month in which you can book a flight from Clearwater to Chicago (average of $245). Flying from Clearwater to Chicago in March is currently the most expensive (average of $321). 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 September 11, 2025.

When flying from Clearwater to Chicago, 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 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 Saturday evenings when fares are most often at their lowest. Saturday at noon 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 September 11, 2025.

The most flights from CL9 to CHI are scheduled on a Thursday (73 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 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 September 11, 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
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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 $140, Frontier can have you in Chicago from Clearwater in 2h 40m. There are 998 mi between Clearwater and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Clearwater to Chicago one-way?

    The cheapest airlines for a one-way flight from Clearwater to Chicago are Southwest ($67), American Airlines ($67), and United Airlines ($67).

  • 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: Brussels Airlines (80%), Cathay Pacific (79%), United Airlines (78%).

  • What are the cheapest flights from Clearwater to Chicago?

    Looking at all options, your cheapest flight can be booked for $52. While the most popular route (Tampa - Chicago O'Hare Intl) can be booked for $80 on average, our data indicates $1,006 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, August is the cheapest month in which you can book a flight from Clearwater to Chicago (average of $245). Flying from Clearwater to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Chesterton

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$48Average$162FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$60Average$162FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$71Average$144FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$407FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$143Average$298FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$369FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$315FlexibilityNo cancel feeOn-time71%

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