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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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
feb. 28 — mar. 71
sáb. 2/28
sáb. 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Clearwater to Chicago are usually found in February or October, booked 86 days in advance, depart on a Friday or Thursday and return on a Wednesday

Cheap 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 enero 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
mar. 3/36:38 pm
TPA
-
ORD
1 stop6h 09m
Multiple Airlines
dom. 3/85:05 pm
ORD
-
TPA
Nonstop3h 00m
Multiple Airlines
Deal found 1/27$89
This CheapOair deal was found by Cheapflights users on 1/27. 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.
jue. 2/123:01 pm
TPA
-
ORD
Nonstop3h 02m
Spirit Airlines
mar. 2/1710:19 am
ORD
-
TPA
Nonstop2h 47m
Spirit Airlines
Deal found 1/27$90
This Priceline deal was found by Cheapflights users on 1/27. 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.
mar. 2/246:38 pm
TPA
-
ORD
1 stop6h 09m
Spirit Airlines
mié. 2/2510:19 am
ORD
-
TPA
Nonstop2h 47m
Spirit Airlines
Deal found 1/27$91
This Super.com deal was found by Cheapflights users on 1/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/273:01 pm
TPA
-
ORD
Nonstop3h 02m
Spirit Airlines
sáb. 2/288:16 pm
ORD
-
TPA
1 stop10h 19m
Spirit Airlines
Deal found 1/29$93
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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.
mar. 2/248:30 am
TPA
-
ORD
1 stop11h 41m
Spirit Airlines
mar. 3/310:19 am
ORD
-
TPA
Nonstop2h 47m
Spirit Airlines
Deal found 1/28$94
This Expedia deal was found by Cheapflights users on 1/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/263:01 pm
TPA
-
ORD
Nonstop3h 02m
Spirit Airlines
dom. 3/18:16 pm
ORD
-
TPA
1 stop10h 19m
Spirit Airlines
Deal found 1/29$95
This CheapOair deal was found by Cheapflights users on 1/27. 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.
mié. 2/253:01 pm
TPA
-
ORD
Nonstop3h 02m
Spirit Airlines
jue. 2/268:16 pm
ORD
-
TPA
1 stop10h 19m
Spirit Airlines
Deal found 1/27$96
This Super.com deal was found by Cheapflights users on 1/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/59:12 pm
TPA
-
ORD
Nonstop3h 04m
Frontier
sáb. 2/79:15 am
ORD
-
TPA
Nonstop2h 57m
Frontier
Deal found 1/28$97
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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.
jue. 2/266:38 pm
TPA
-
ORD
1 stop6h 09m
Spirit Airlines
lun. 3/210:19 am
ORD
-
TPA
Nonstop2h 47m
Spirit Airlines
Deal found 1/27$98
This Frontier deal was found by Cheapflights users on 1/27. 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.
jue. 2/265:23 pm
TPA
-
ORD
Nonstop3h 14m
Frontier
sáb. 2/284:42 pm
ORD
-
TPA
1 stop6h 43m
Frontier
Deal found 1/27$99
This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/146:38 pm
TPA
-
ORD
1 stop6h 09m
Spirit Airlines
lun. 2/1610:19 am
ORD
-
TPA
Nonstop2h 47m
Spirit Airlines
Deal found 1/28$100
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
jue. 2/55:45 am
TPA
-
MDW
1 stop7h 00m
Frontier
jue. 2/55:01 pm
MDW
-
TPA
1 stop6h 25m
Frontier
Deal found 1/28$127

Find flight deals from Clearwater to Chicago

Keep the following information in mind while searching for Clearwater to Chicago flight deals. Data was last updated enero 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$89
(Kiwi.com)

One-way from

$67
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$192
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. 7% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 enero 29, 2026.
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

mié. 2/25

3:01 pm-5:03 pm

Nonstop3h 02m

Chicago O'Hare Intl

mié. 3/4

5:15 am-5:33 pm

1 stop11h 18m

$90

TampaChicago

TPA - ORD

TPAORD

Tampa

jue. 2/26

8:30 am-7:11 pm

1 stop11h 41m

Chicago O'Hare Intl

lun. 3/2

5:15 am-5:33 pm

1 stop11h 18m

$117

TampaChicago

TPA - ORD

TPAORD

Tampa

mié. 3/25

3:11 pm-5:11 pm

Nonstop3h 00m

Chicago O'Hare Intl

lun. 3/30

8:41 pm-7:19 am

1 stop9h 38m

$118

TampaChicago

TPA - ORD

TPAORD

Tampa

jue. 2/26

8:30 am-7:11 pm

1 stop11h 41m

Chicago O'Hare Intl

dom. 3/1

8:16 pm-7:35 am

1 stop10h 19m

$120

TampaChicago

TPA - ORD

TPAORD

Tampa

jue. 3/12

8:14 am-6:21 pm

1 stop11h 07m

Chicago O'Hare Intl

lun. 3/16

10:15 am-1:53 pm

Nonstop2h 38m

$124

TampaChicago

TPA - ORD

TPAORD

Tampa

vie. 2/13

6:38 pm-11:47 pm

1 stop6h 09m

Chicago O'Hare Intl

lun. 2/16

1:44 pm-5:44 pm

Nonstop3h 00m

$141

TampaChicago

TPA - MDW

TPAMDW

Tampa

jue. 2/26

5:55 am-4:16 pm

1 stop11h 21m

Chicago Midway

jue. 3/5

5:16 pm-12:25 am

1 stop6h 09m

$154

TampaChicago

TPA - MDW

TPAMDW

Tampa

sáb. 2/28

6:50 am-8:35 am

Nonstop2h 45m

Chicago Midway

sáb. 3/7

9:40 pm-1:15 am

Nonstop2h 35m

$177

TampaChicago

TPA - MDW

TPAMDW

Tampa

vie. 2/27

6:40 am-8:25 am

Nonstop2h 45m

Chicago Midway

dom. 3/1

4:35 pm-12:05 am

1 stop6h 30m

$198

TampaChicago

TPA - MDW

TPAMDW

Tampa

sáb. 3/7

11:30 am-8:21 pm

1 stop9h 51m

Chicago Midway

lun. 3/9

2:41 pm-9:00 pm

1 stop5h 19m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

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 January 23, 2026.

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, March is the cheapest month in which you can book a flight from Clearwater to Chicago (average of $43). 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 enero 29, 2026.

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 January 24, 2026.

Travelers seeking maximum savings on their Clearwater to Chicago flight should consider departing on Saturday 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 enero 29, 2026.

The most flights from CL9 to CHI are scheduled on a Monday (64 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (21 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 enero 29, 2026.
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
4,267 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

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
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

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
9,215 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

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
11,205 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

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
8,394 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

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
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

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 $177, Spirit Airlines can have you in Chicago from Clearwater in 2h 45m. 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 Frontier ($40), Spirit Airlines ($46), and Southwest ($71).

  • 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: Cathay Pacific (87%), Royal Jordanian (82%), Austrian Airlines (81%).

  • What are the cheapest flights from Clearwater to Chicago?

    Looking at all options, your cheapest flight can be booked for $60. While the most popular route (Tampa - Chicago O'Hare Intl) can be booked for $70 on average, our data indicates $1,179 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, March is the cheapest month in which you can book a flight from Clearwater to Chicago (average of $43). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 enero 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$155FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$68Average$153FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$70Average$168FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$366FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$145Average$296FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$150Average$342FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$308FlexibilityNo cancel feeOn-time71%

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