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$45+ 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 4/12. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
1 adult, Economy
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Cheapflights Tip: The best prices from Clearwater to Chicago are usually found in September or January, booked 75 days in advance, depart on a Thursday or Friday and return on a Tuesday

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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$93
(Kiwi.com)

One-way from

$45
(Cheapflightsfares)

Popular in

October

Cheapest in

September

Average price

$226
Provider with most accurate pricing for Tampa-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Tampa-Chicago (CHI) flights.
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From Clearwater to Chicago (CHI)
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One-way flight from Clearwater to Chicago (CHI)
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Highest demand for flights based on searches. 0% potential increase in price ($0 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 31, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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 4/129:20 pmTPA - ORD
Nonstop2h 56mSpirit Airlines
Tue 4/159:30 amORD - TPA
Nonstop2h 48mSpirit Airlines
Deal found 3/30$91
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/3010:25 pmTPA - ORD
Nonstop2h 56mMultiple Airlines
Sat 5/109:19 amORD - TPA
Nonstop2h 46mMultiple Airlines
Deal found 3/31$93
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Sat 4/129:42 pmTPA - ORD
Nonstop3h 04mFrontier
Tue 4/159:32 amORD - TPA
Nonstop2h 48mFrontier
Deal found 3/31$102
This Frontier deal was found by Cheapflights users on 3/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/128:45 pmTPA - MDW
Nonstop2h 51mFrontier
Tue 4/155:03 pmMDW - TPA
Nonstop2h 43mFrontier
Deal found 3/31$104
This Southwest deal was found by Cheapflights users on 3/29. 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.
Wed 5/147:25 amTPA - MDW
Nonstop2h 45mSouthwest
Wed 5/2110:05 amMDW - TPA
1 stop3h 55mSouthwest
Deal found 3/29$189
This Delta deal was found by Cheapflights users on 3/29. 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.
Wed 5/75:20 amTPA - MDW
1 stop5h 20mDelta
Tue 5/206:00 amMDW - TPA
1 stop5h 30mDelta
Deal found 3/29$197
This American Airlines deal was found by Cheapflights users on 3/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/27:00 amTPA - ORD
Nonstop3h 13mAmerican Airlines
Fri 5/26:00 pmORD - TPA
Nonstop2h 51mAmerican Airlines
Deal found 3/31$217
This United Airlines deal was found by Cheapflights users on 3/30. 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 7/1812:38 pmTPA - ORD
Nonstop3h 04mUnited Airlines
Sun 7/207:30 amORD - TPA
Nonstop2h 51mUnited Airlines
Deal found 3/30$237
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/168:30 amTPA - ORD
1 stop6h 50mDelta
Thu 7/247:00 amORD - TPA
1 stop4h 49mDelta
Deal found 3/31$247
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Thu 4/245:35 amTPA - RFD
1 stop16h 11mMultiple Airlines
Sun 4/279:36 pmRFD - TPA
1 stop29h 54mMultiple Airlines
Deal found 3/30$415

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 March 31, 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

Sat 4/12

9:20 pm-11:16 pm

Nonstop2h 56m

Chicago O'Hare Intl

Tue 4/15

9:30 am-1:18 pm

Nonstop2h 48m

$91

TampaChicago

TPA - ORD

TPAORD

Tampa

Tue 5/6

9:20 pm-11:16 pm

Nonstop2h 56m

Chicago O'Hare Intl

Sat 5/10

9:19 am-1:05 pm

Nonstop2h 46m

$107

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 4/10

9:51 am-11:43 am

Nonstop2h 52m

Chicago Midway

Wed 4/16

3:00 pm-6:41 pm

Nonstop2h 41m

$111

TampaChicago

TPA - ORD

TPAORD

Tampa

Thu 4/10

1:03 pm-3:06 pm

Nonstop3h 03m

Chicago O'Hare Intl

Wed 4/16

2:00 pm-5:48 pm

Nonstop2h 48m

$111

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 5/14

7:25 am-9:10 am

Nonstop2h 45m

Chicago Midway

Wed 5/21

10:05 am-3:00 pm

1 stop3h 55m

$189

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 6/7

6:30 am-12:28 pm

1 stop6h 58m

Chicago Midway

Tue 6/10

6:00 am-11:37 am

1 stop4h 37m

$207

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 7/16

12:18 pm-4:46 pm

1 stop5h 28m

Chicago O'Hare Intl

Fri 7/25

7:10 am-1:43 pm

1 stop5h 33m

$247

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 7/30

6:50 pm-8:57 pm

Nonstop3h 07m

Chicago O'Hare Intl

Sun 8/3

5:15 am-11:16 am

1 stop5h 01m

$256

TampaChicago

TPA - RFD

TPARFD

Tampa

Thu 4/24

5:35 am-8:46 pm

1 stop16h 11m

Chicago Greater Rockford

Sun 4/27

9:36 pm-4:30 am

1 stop29h 54m

$415

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 4/12

9:20 pm-11:16 pm

Nonstop2h 56m

$45

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 22 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 March 28, 2025.

To ensure you get the cheapest price possible for a flight from Clearwater to Chicago, you should look to book at least 75 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 $323). 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 March 31, 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 Thursday evenings when fares are most often at their lowest. Tuesday 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 March 31, 2025.

The most flights from CL9 to CHI are scheduled on a Monday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 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 March 31, 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
4,276 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

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
4,276 reviews
Southwest
8.0
Very good
4,276 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

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
7,899 reviews
Southwest
8.0
Very good
4,276 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

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
8,614 reviews
Southwest
8.0
Very good
4,276 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

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
4,276 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

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.
Sun Country Air
6.9
Okay
349 reviews
Southwest
8.0
Very good
4,276 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

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 Spirit Airlines ($45), Frontier ($49), and Southwest ($88).

  • 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: Japan Airlines (98%), Cathay Pacific (98%), Frontier (97%).

  • 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 $91 on average our data indicates $2,357 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 $323). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$147FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$158FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$109Average$184FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$155Average$361FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$156Average$347FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$156Average$311FlexibilityNo cancel feeOn-time71%
DeltaCheapest$175Average$473FlexibilityNo cancel feeOn-timeN/A
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