HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$58+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
abr. 27 — may. 41
dom. 4/27
dom. 5/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Clearwater to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 abril 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$100
(Kiwi.com)

One-way from

$58
(Cheapflightsfares)

Popular in

April

Cheapest in

September

Average price

$253
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. 3% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

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 abril 22, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
sáb. 5/102:00 pmTPA - ORD
Nonstop3h 03mMultiple Airlines
mar. 5/136:30 amORD - TPA
Nonstop2h 38mMultiple Airlines
Deal found 4/22$100
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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. 5/206:08 pmTPA - ORD
Nonstop3h 00mSpirit Airlines
mar. 5/276:30 amORD - TPA
Nonstop2h 38mSpirit Airlines
Deal found 4/22$105
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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. 5/228:49 pmTPA - MDW
Nonstop2h 52mFrontier
jue. 5/294:11 pmMDW - TPA
Nonstop2h 43mFrontier
Deal found 4/22$121
This Frontier deal was found by Cheapflights users on 4/22. 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.
sáb. 5/245:43 pmTPA - ORD
Nonstop3h 05mFrontier
jue. 5/296:16 pmORD - TPA
Nonstop2h 46mFrontier
Deal found 4/22$123
This Southwest deal was found by Cheapflights users on 4/21. 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.
mié. 5/217:25 amTPA - MDW
Nonstop2h 45mSouthwest
mar. 5/276:55 amMDW - TPA
Nonstop2h 30mSouthwest
Deal found 4/21$168
This American Airlines deal was found by Cheapflights users on 4/21. 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.
mié. 5/217:20 amTPA - ORD
Nonstop3h 05mAmerican Airlines
mié. 5/215:57 pmORD - TPA
Nonstop2h 38mAmerican Airlines
Deal found 4/21$193
This Delta deal was found by Cheapflights users on 4/22. 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.
mié. 6/45:20 amTPA - MDW
1 stop5h 20mDelta
mié. 6/116:00 amMDW - TPA
1 stop5h 37mDelta
Deal found 4/22$197
This Delta deal was found by Cheapflights users on 4/22. 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.
mar. 6/35:53 pmTPA - ORD
1 stop7h 05mDelta
mié. 6/117:10 amORD - TPA
1 stop4h 27mDelta
Deal found 4/22$197
This Southwest deal was found by Cheapflights users on 4/22. 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.
mar. 6/37:15 amTPA - ORD
1 stop5h 35mSouthwest
mar. 6/101:30 pmORD - TPA
2 stops8h 50mSouthwest
Deal found 4/22$242
This Mytrip deal was found by Cheapflights users on 4/21. 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.
vie. 7/1811:15 amTPA - RFD
3 stops23h 58mMultiple Airlines
mié. 7/239:44 amRFD - TPA
2 stops31h 25mMultiple Airlines
Deal found 4/21$474

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 abril 22, 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

sáb. 5/10

2:00 pm-4:03 pm

Nonstop3h 03m

Chicago O'Hare Intl

mar. 5/13

6:30 am-10:08 am

Nonstop2h 38m

$100

TampaChicago

TPA - ORD

TPAORD

Tampa

mar. 5/20

6:08 pm-8:08 pm

Nonstop3h 00m

Chicago O'Hare Intl

mar. 5/27

6:30 am-10:08 am

Nonstop2h 38m

$105

TampaChicago

TPA - ORD

TPAORD

Tampa

sáb. 5/24

5:43 pm-7:48 pm

Nonstop3h 05m

Chicago O'Hare Intl

jue. 5/29

6:16 pm-10:02 pm

Nonstop2h 46m

$123

TampaChicago

TPA - MDW

TPAMDW

Tampa

jue. 5/22

8:49 pm-10:41 pm

Nonstop2h 52m

Chicago Midway

dom. 6/1

4:06 pm-7:49 pm

Nonstop2h 43m

$125

TampaChicago

TPA - MDW

TPAMDW

Tampa

mié. 5/21

7:25 am-9:10 am

Nonstop2h 45m

Chicago Midway

mar. 5/27

6:55 am-10:25 am

Nonstop2h 30m

$168

TampaChicago

TPA - ORD

TPAORD

Tampa

mié. 5/21

7:20 am-9:25 am

Nonstop3h 05m

Chicago O'Hare Intl

mié. 5/21

5:57 pm-9:35 pm

Nonstop2h 38m

$193

TampaChicago

TPA - MDW

TPAMDW

Tampa

mié. 6/4

5:20 am-9:40 am

1 stop5h 20m

Chicago Midway

mié. 6/11

6:00 am-12:37 pm

1 stop5h 37m

$197

TampaChicago

TPA - ORD

TPAORD

Tampa

mar. 6/3

5:53 pm-11:58 pm

1 stop7h 05m

Chicago O'Hare Intl

mié. 6/11

7:10 am-12:37 pm

1 stop4h 27m

$197

TampaChicago

TPA - ORD

TPAORD

Tampa

mar. 6/3

7:15 am-11:50 am

1 stop5h 35m

Chicago O'Hare Intl

mar. 6/10

1:30 pm-11:20 pm

2 stops8h 50m

$242

TampaChicago

TPA - RFD

TPARFD

Tampa

vie. 7/18

11:15 am-10:13 am

3 stops23h 58m

Chicago Greater Rockford

mié. 7/23

9:44 am-6:09 pm

2 stops31h 25m

$474

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 24 results
1
2
3

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 April 18, 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 $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 abril 22, 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. 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 abril 22, 2025.

The most flights from CL9 to CHI are scheduled on a Monday (64 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (33 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 abril 22, 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
4,286 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

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
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

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.
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

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
8,683 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

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
10,000 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

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
7,940 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

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.

  • 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 ($58), Spirit Airlines ($66), and Southwest ($80).

  • 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 (95%), Azul (90%), ANA (89%).

  • 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 $105 on average our data indicates $995 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Clearwater to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Orlando to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Miami to O'Hare Intl flights
Tampa to O'Hare Intl flights
Jacksonville to O'Hare Intl flights
West Palm Beach to O'Hare Intl flights
Orlando to Midway flights
Sarasota to O'Hare Intl flights
Fort Myers to O'Hare Intl flights
Tampa to Midway flights
Miami to Midway flights
Orlando to St. Louis flights
West Palm Beach to Midway flights
Fort Lauderdale to Midway flights
Jacksonville to Midway flights
Pensacola to O'Hare Intl flights
Miami to St. Louis flights
Tampa to St. Louis flights
Fort Myers to Midway flights
Sarasota to Midway flights
Pensacola to Midway flights
Panama City to O'Hare Intl flights
Jacksonville to St. Louis flights
Fort Lauderdale to St. Louis flights
West Palm Beach to St. Louis flights
Sarasota to St. Louis flights
Valparaiso to O'Hare Intl flights
St Petersburg to Rockford flights
Fort Myers to St. Louis flights
Orlando to Bloomington flights
Orlando to Moline flights
Gainesville to O'Hare Intl flights
Tallahassee to O'Hare Intl flights
Tampa to Moline flights
Jacksonville to Peoria flights
Panama City to Midway flights
Orlando to Peoria flights
Melbourne to St. Louis flights
Orlando Sanford Intl to Rockford flights
Gainesville to St. Louis flights
Jacksonville to Moline flights
Key West to O'Hare Intl flights
Orlando to Rockford flights
Gainesville to Midway flights
Daytona Beach to O'Hare Intl flights
Melbourne to O'Hare Intl flights
Valdosta to O'Hare Intl flights
Pensacola to St. Louis flights
Tallahassee to Midway flights
Panama City to St. Louis flights

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 abril 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$48Average$149FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$163FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$100Average$184FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$155Average$356FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$156Average$315FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$157Average$356FlexibilityNo cancel feeOn-time69%
DeltaCheapest$196Average$471FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.