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$67+ 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 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
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Cheapflights Tip: The best prices from Clearwater to Chicago are usually found in January or February, booked 70 days in advance, depart on a Thursday or Friday 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 August 13, 2025.

Round-trip from

$113
(Priceline)

One-way from

$67
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$209
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 ($19 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 August 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 August 13, 2025.

This Mytrip deal was found by Cheapflights users on 8/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1510:17 pmTPA - ORD
Nonstop3h 08mFrontier
Sun 8/246:10 amORD - TPA
Nonstop2h 52mFrontier
Deal found 8/13$112
This Priceline deal was found by Cheapflights users on 8/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:01 amTPA - ORD
Nonstop3h 09mMultiple Airlines
Mon 9/85:46 pmORD - TPA
Nonstop2h 45mMultiple Airlines
Deal found 8/13$113
This Frontier deal was found by Cheapflights users on 8/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1510:55 amTPA - MDW
Nonstop2h 49mFrontier
Fri 9/196:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 8/11$114
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/226:29 amTPA - ORD
Nonstop3h 08mFrontier
Mon 8/259:32 amORD - TPA
Nonstop2h 52mFrontier
Deal found 8/12$114
This FlightHub deal was found by Cheapflights users on 8/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/25:01 amTPA - ORD
Nonstop3h 09mMultiple Airlines
Mon 10/65:46 pmORD - TPA
Nonstop2h 45mMultiple Airlines
Deal found 8/11$115
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3110:55 amTPA - MDW
Nonstop2h 49mFrontier
Sun 11/25:21 amMDW - TPA
Nonstop2h 39mFrontier
Deal found 8/12$116
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/58:15 amTPA - ORD
Nonstop3h 03mMultiple Airlines
Sun 9/78:05 amORD - TPA
Nonstop3h 00mMultiple Airlines
Deal found 8/12$116
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2210:55 amTPA - MDW
Nonstop2h 49mFrontier
Fri 9/266:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 8/11$117
This Priceline deal was found by Cheapflights users on 8/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/256:29 amTPA - ORD
Nonstop3h 08mMultiple Airlines
Sat 8/305:21 pmORD - TPA
Nonstop2h 39mMultiple Airlines
Deal found 8/12$117
This Frontier deal was found by Cheapflights users on 8/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2610:55 amTPA - MDW
Nonstop2h 49mFrontier
Sun 9/286:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 8/11$118
This Cheapflightsfares deal was found by Cheapflights users on 8/11. 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 10/178:15 amTPA - ORD
Nonstop3h 03mSpirit Airlines
Wed 10/225:46 pmORD - TPA
Nonstop2h 45mSpirit Airlines
Deal found 8/11$118
This Frontier deal was found by Cheapflights users on 8/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1910:55 amTPA - MDW
Nonstop2h 49mFrontier
Mon 9/226:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 8/11$119

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 August 13, 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 9/4

5:01 am-7:10 am

Nonstop3h 09m

Chicago O'Hare Intl

Mon 9/8

5:46 pm-9:31 pm

Nonstop2h 45m

$113

TampaChicago

TPA - ORD

TPAORD

Tampa

Mon 9/8

8:15 am-10:18 am

Nonstop3h 03m

Chicago O'Hare Intl

Sun 9/14

8:05 am-12:05 pm

Nonstop3h 00m

$113

TampaChicago

TPA - ORD

TPAORD

Tampa

Thu 9/25

5:01 am-7:10 am

Nonstop3h 09m

Chicago O'Hare Intl

Mon 9/29

5:46 pm-9:31 pm

Nonstop2h 45m

$113

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 10/3

10:55 am-12:44 pm

Nonstop2h 49m

Chicago Midway

Sun 10/5

6:21 am-9:57 am

Nonstop2h 36m

$114

TampaChicago

TPA - MDW

TPAMDW

Tampa

Mon 9/15

10:55 am-12:44 pm

Nonstop2h 49m

Chicago Midway

Fri 9/19

6:21 am-9:57 am

Nonstop2h 36m

$114

TampaChicago

TPA - ORD

TPAORD

Tampa

Thu 10/9

11:04 am-1:04 pm

Nonstop3h 00m

Chicago O'Hare Intl

Thu 10/16

5:46 pm-9:31 pm

Nonstop2h 45m

$115

TampaChicago

TPA - ORD

TPAORD

Tampa

Sun 8/31

10:57 am-1:05 pm

Nonstop3h 08m

Chicago O'Hare Intl

Fri 9/5

5:46 pm-9:31 pm

Nonstop2h 45m

$115

TampaChicago

TPA - ORD

TPAORD

Tampa

Thu 10/2

5:01 am-7:10 am

Nonstop3h 09m

Chicago O'Hare Intl

Mon 10/6

5:46 pm-9:31 pm

Nonstop2h 45m

$115

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 10/31

10:55 am-12:44 pm

Nonstop2h 49m

Chicago Midway

Sun 11/2

5:21 am-9:00 am

Nonstop2h 39m

$116

TampaChicago

TPA - ORD

TPAORD

Tampa

Thu 9/25

5:01 am-7:10 am

Nonstop3h 09m

Chicago O'Hare Intl

Tue 9/30

5:46 pm-9:31 pm

Nonstop2h 45m

$116

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 57 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 August 8, 2025.

To ensure you get the cheapest price possible for a flight from Clearwater to Chicago, you should look to book at least 70 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 August 13, 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 August 13, 2025.

The most flights from CL9 to CHI are scheduled on a Monday (72 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (47 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 August 13, 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
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
8,920 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
8,048 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
3,221 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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.

  • 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 (90%), Austrian Airlines (89%), Cathay Pacific (84%).

  • What are the cheapest flights from Clearwater to Chicago?

    Looking at all options, your cheapest flight can be booked for $53. While the most popular route (Tampa - Chicago O'Hare Intl) can be booked for $85 on average our data indicates $1,047 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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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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$48Average$163FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$60Average$168FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$70Average$153FlexibilityNo cancel feeOn-time65%
DeltaCheapest$98Average$455FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$158Average$367FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$312FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$159Average$330FlexibilityNo cancel feeOn-time63%

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