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$71+ 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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 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 June 12, 2025.

Round-trip from

$129
(Kiwi.com)

One-way from

$71
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$247
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).
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Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Wed 7/91:32 pmTPA - ORD
Nonstop3h 10mSpirit Airlines
Thu 7/108:50 amORD - TPA
Nonstop2h 47mSpirit Airlines
Deal found 6/11$129
This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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 8/810:17 pmTPA - ORD
Nonstop3h 08mFrontier
Mon 8/115:28 pmORD - TPA
Nonstop2h 52mFrontier
Deal found 6/12$137
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/215:01 amTPA - MDW
1 stop6h 07mFrontier
Mon 8/259:10 amMDW - TPA
1 stop5h 13mFrontier
Deal found 6/9$143
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 7/91:32 pmTPA - ORD
Nonstop3h 10mMultiple Airlines
Thu 7/177:05 amORD - TPA
Nonstop2h 52mMultiple Airlines
Deal found 6/10$145
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/52:50 pmTPA - MDW
Nonstop2h 35mSouthwest
Tue 8/126:10 pmMDW - TPA
Nonstop2h 40mSouthwest
Deal found 6/10$157
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/97:00 amTPA - ORD
Nonstop3h 05mAmerican Airlines
Tue 10/146:02 pmORD - TPA
Nonstop2h 50mAmerican Airlines
Deal found 6/11$157
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/235:40 amTPA - RFD
2 stops27h 51mMultiple Airlines
Thu 7/319:21 amRFD - TPA
1 stop5h 40mMultiple Airlines
Deal found 6/11$178
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/96:30 amTPA - MDW
1 stop4h 15mDelta
Wed 8/136:04 amMDW - TPA
1 stop4h 23mDelta
Deal found 6/12$197
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/125:20 amTPA - ORD
1 stop5h 50mDelta
Wed 7/167:00 amORD - TPA
1 stop7h 23mDelta
Deal found 6/11$197
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/277:30 amTPA - ORD
Nonstop3h 04mUnited Airlines
Wed 7/305:55 pmORD - TPA
Nonstop2h 50mUnited Airlines
Deal found 6/11$229
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/55:55 amTPA - ORD
2 stops7h 50mSouthwest
Sun 9/74:20 pmORD - TPA
1 stop7h 25mSouthwest
Deal found 6/10$257

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 June 12, 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 7/9

1:32 pm-3:42 pm

Nonstop3h 10m

Chicago O'Hare Intl

Thu 7/10

8:50 am-12:37 pm

Nonstop2h 47m

$129

TampaChicago

TPA - ORD

TPAORD

Tampa

Fri 8/8

10:17 pm-12:25 am

Nonstop3h 08m

Chicago O'Hare Intl

Mon 8/11

5:28 pm-9:20 pm

Nonstop2h 52m

$137

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 8/21

5:01 am-10:08 am

1 stop6h 07m

Chicago Midway

Mon 8/25

9:10 am-3:23 pm

1 stop5h 13m

$143

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 7/9

1:32 pm-3:42 pm

Nonstop3h 10m

Chicago O'Hare Intl

Thu 7/17

7:05 am-10:57 am

Nonstop2h 52m

$145

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 8/5

2:50 pm-4:25 pm

Nonstop2h 35m

Chicago Midway

Tue 8/12

6:10 pm-9:50 pm

Nonstop2h 40m

$157

TampaChicago

TPA - RFD

TPARFD

Tampa

Wed 7/23

5:40 am-8:31 am

2 stops27h 51m

Chicago Greater Rockford

Thu 7/31

9:21 am-4:01 pm

1 stop5h 40m

$178

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 8/9

8:50 am-11:58 am

1 stop4h 08m

Chicago Midway

Thu 8/14

6:04 am-12:30 pm

1 stop5h 26m

$197

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 7/12

6:00 am-10:15 am

1 stop5h 15m

Chicago O'Hare Intl

Tue 7/15

5:20 pm-11:01 pm

1 stop4h 41m

$197

TampaChicago

TPA - ORD

TPAORD

Tampa

Fri 6/27

7:30 am-9:34 am

Nonstop3h 04m

Chicago O'Hare Intl

Wed 7/30

5:55 pm-9:45 pm

Nonstop2h 50m

$229

TampaChicago

TPA - ORD

TPAORD

Tampa

Fri 9/5

5:55 am-12:45 pm

2 stops7h 50m

Chicago O'Hare Intl

Sun 9/7

4:20 pm-12:45 am

1 stop7h 25m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 22 results
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2
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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 June 9, 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 June 12, 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 June 12, 2025.

The most flights from CL9 to CHI are scheduled on a Thursday (75 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
To help decide which airline to fly from Clearwater to Chicago, see what other customers have to say about Southwest, Delta and United Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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
8,052 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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 cheapest airlines to fly from Clearwater to Chicago one-way?

    The cheapest airlines for a one-way flight from Clearwater to Chicago are Frontier ($71), Spirit Airlines ($73), and Southwest ($79).

  • 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: ANA (91%), SWISS (89%), Japan Airlines (87%).

  • What are the cheapest flights from Clearwater to Chicago?

    Looking at all options, your cheapest flight can be booked for $55. While the most popular route (Tampa - Chicago O'Hare Intl) can be booked for $125 on average our data indicates $1,437 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 Clearwater?

Book flights to Clearwater if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$48Average$155FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$161FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$97Average$171FlexibilityNo cancel feeOn-time88%
DeltaCheapest$138Average$428FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$156Average$359FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$313FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$160Average$340FlexibilityNo cancel feeOn-time63%

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