HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$72+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 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 July 3, 2025.

Round-trip from

$130
(FlightHub)

One-way from

$72
(FlightHub)

Popular in

June

Cheapest in

January

Average price

$199
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 ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 3, 2025.

This FlightHub deal was found by Cheapflights users on 7/1. 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.
Fri 9/54:53 pmTPA - MDW
1 stop7h 27mFrontier
Sun 9/146:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 7/1$130
This Priceline deal was found by Cheapflights users on 7/1. 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.
Sat 7/195:04 pmTPA - ORD
Nonstop3h 16mFrontier
Tue 7/225:01 amORD - TPA
1 stop8h 14mFrontier
Deal found 7/1$130
This Priceline deal was found by Cheapflights users on 7/3. 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 7/247:19 pmTPA - ORD
1 stop6h 03mMultiple Airlines
Wed 7/308:50 amORD - TPA
Nonstop2h 47mMultiple Airlines
Deal found 7/3$131
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Tue 7/225:15 pmTPA - ORD
Nonstop3h 11mSpirit Airlines
Sat 7/268:50 amORD - TPA
Nonstop2h 47mSpirit Airlines
Deal found 7/1$137
This Southwest deal was found by Cheapflights users on 7/1. 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 8/57:15 amTPA - MDW
Nonstop2h 40mSouthwest
Wed 8/66:10 pmMDW - TPA
Nonstop2h 40mSouthwest
Deal found 7/1$157
This Mytrip deal was found by Cheapflights users on 7/2. 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 8/146:00 amTPA - RFD
2 stops9h 51mMultiple Airlines
Sun 8/173:41 pmRFD - TPA
2 stops16h 43mMultiple Airlines
Deal found 7/2$249

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 July 3, 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 - MDW

TPAMDW

Tampa

Fri 9/5

6:00 am-11:20 pm

1 stop18h 20m

Chicago Midway

Sun 9/7

6:21 am-9:57 am

Nonstop2h 36m

$130

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 7/19

5:04 pm-7:20 pm

Nonstop3h 16m

Chicago O'Hare Intl

Tue 7/22

5:01 am-2:15 pm

1 stop8h 14m

$130

TampaChicago

TPA - ORD

TPAORD

Tampa

Thu 7/24

7:19 pm-12:22 am

1 stop6h 03m

Chicago O'Hare Intl

Wed 7/30

8:50 am-12:37 pm

Nonstop2h 47m

$131

TampaChicago

TPA - ORD

TPAORD

Tampa

Tue 7/22

5:15 pm-7:26 pm

Nonstop3h 11m

Chicago O'Hare Intl

Sat 7/26

8:50 am-12:37 pm

Nonstop2h 47m

$137

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 8/5

7:15 am-8:55 am

Nonstop2h 40m

Chicago Midway

Wed 8/6

6:10 pm-9:50 pm

Nonstop2h 40m

$157

TampaChicago

TPA - RFD

TPARFD

Tampa

Thu 8/14

6:00 am-2:51 pm

2 stops9h 51m

Chicago Greater Rockford

Sun 8/17

3:41 pm-9:24 am

2 stops16h 43m

$249

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sun 8/10

8:32 pm-10:24 pm

Nonstop2h 52m

$72

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 8/23

5:01 am-11:36 am

1 stop7h 35m

$72

TampaChicago

TPA - ORD

TPAORD

Tampa

Tue 8/5

5:15 pm-7:26 pm

Nonstop3h 11m

$73

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 8/13

7:15 am-8:55 am

Nonstop2h 40m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 16 results
1
2

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 27, 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 July 3, 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 July 3, 2025.

The most flights from CL9 to CHI are scheduled on a Thursday (74 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (23 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 July 3, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United 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
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

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
4,270 reviews
Southwest
8.0
Very good
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

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
7,970 reviews
Southwest
8.0
Very good
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

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
8,845 reviews
Southwest
8.0
Very good
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

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
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

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
8,094 reviews
Southwest
8.0
Very good
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

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 ($72), 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: Brussels Airlines (95%), Austrian Airlines (94%), SWISS (89%).

  • What are the cheapest flights from Clearwater to Chicago?

    Looking at all options, your cheapest flight can be booked for $63. While the most popular route (Tampa - Chicago O'Hare Intl) can be booked for $104 on average our data indicates $2,335 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

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.
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Orlando to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Tampa to Midway flights
Orlando to Midway flights
West Palm Beach to O'Hare Intl flights
Miami to Midway flights
Jacksonville to O'Hare Intl flights
Fort Myers to O'Hare Intl flights
Pensacola to O'Hare Intl flights
Sarasota to O'Hare Intl flights
Fort Lauderdale to Midway flights
West Palm Beach to Midway flights
Orlando to St. Louis flights
Valparaiso to O'Hare Intl flights
Miami to St. Louis flights
Jacksonville to Midway flights
Fort Lauderdale to St. Louis flights
Fort Myers to Midway flights
Tampa to St. Louis flights
Valparaiso to Midway flights
Pensacola to Midway flights
Sarasota to Midway flights
Panama City to O'Hare Intl flights
Jacksonville to St. Louis flights
Fort Myers to St. Louis flights
Tampa to Peoria flights
Tallahassee to O'Hare Intl flights
West Palm Beach to St. Louis flights
Gainesville to O'Hare Intl flights
Panama City to Midway flights
Melbourne to St. Louis flights
Orlando Sanford Intl to Rockford flights
Pensacola to St. Louis flights
Sarasota to St. Louis flights
Jacksonville to Peoria flights
Daytona Beach to St. Louis flights
Daytona Beach to O'Hare Intl flights
Orlando to Moline flights
St Petersburg to Rockford flights
Fort Lauderdale to Rockford flights
Gainesville to Midway flights
Orlando to Bloomington flights
Valparaiso to St. Louis flights
Panama City to St. Louis flights
Tallahassee to Midway flights
Key West to O'Hare Intl flights
Orlando to Peoria 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$48Average$159FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$158FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$90Average$170FlexibilityNo cancel feeOn-time88%
DeltaCheapest$138Average$443FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$156Average$364FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$314FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$160Average$338FlexibilityNo cancel feeOn-time63%

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.