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$38+ 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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Nov 9 — Nov 161
Sat 11/9
Sat 11/16
1 adult, Economy
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The best prices from Clearwater to Chicago are usually found in February or January, booked 89 days in advance, depart on a Friday or Wednesday and return on a Tuesday

Cheap flight deals from Clearwater to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Clearwater (CL9) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 4, 2024.

Popular in

March

Cheapest in

February

Round-trip from

$78
(Frontier)

One-way from

$38
(Cheapflightsfares)
High demand for flights, 22% potential price rise
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Best time to find cheap flights, 29% potential price drop
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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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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 November 4, 2024.

This eDestinos deal was found by Cheapflights users on 11/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/51:08 pmTPA - ORD
Nonstop3h 05mSpirit Airlines
Sat 12/711:25 amORD - TPA
Nonstop2h 50mSpirit Airlines
Deal found 11/3$95
This FlightHub deal was found by Cheapflights users on 11/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/137:35 amTPA - ORD
Nonstop3h 03mMultiple Airlines
Tue 12/175:45 amORD - TPA
Nonstop2h 56mMultiple Airlines
Deal found 11/3$96
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/178:46 pmTPA - MDW
Nonstop2h 47mFrontier
Mon 12/306:00 amMDW - TPA
Nonstop2h 46mFrontier
Deal found 11/3$99
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1811:39 amTPA - ORD
Nonstop3h 10mFrontier
Wed 12/1810:22 pmORD - TPA
1 stop8h 31mFrontier
Deal found 11/3$100
This eDestinos deal was found by Cheapflights users on 11/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/311:26 amTPA - MDW
1 stop25h 16mMultiple Airlines
Tue 12/1012:57 pmMDW - TPA
1 stop19h 39mMultiple Airlines
Deal found 11/3$154
This United Airlines deal was found by Cheapflights users on 11/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/411:15 amTPA - ORD
Nonstop2h 56mUnited Airlines
Sat 12/76:05 pmORD - TPA
Nonstop2h 52mUnited Airlines
Deal found 11/3$157
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1412:20 pmTPA - ORD
1 stop5h 23mDelta
Sun 1/126:55 amORD - TPA
1 stop5h 10mDelta
Deal found 11/3$196
This American Airlines deal was found by Cheapflights users on 11/4. 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.
Wed 12/41:27 pmTPA - ORD
Nonstop3h 00mAmerican Airlines
Thu 12/58:26 amORD - TPA
Nonstop2h 40mAmerican Airlines
Deal found 11/4$202
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/512:33 pmTPA - MDW
1 stop5h 29mDelta
Sun 12/86:00 amMDW - TPA
1 stop4h 14mDelta
Deal found 11/3$206
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/207:25 amTPA - MDW
Nonstop2h 45mSouthwest
Sun 11/248:45 pmMDW - TPA
Nonstop2h 35mSouthwest
Deal found 11/3$237
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/147:00 amTPA - RFD
1 stop13h 51mMultiple Airlines
Sun 11/179:50 pmRFD - TPA
2 stops16h 55mMultiple Airlines
Deal found 11/3$411

Find flights from Clearwater to Chicago within your budget

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 2,455,398 searches. Data last updated November 4, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 2/26

5:05 pm-6:48 pm

Nonstop2h 43m

$46

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 12/14

7:35 am-9:38 am

Nonstop3h 03m

$51

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 12/11

7:25 am-9:10 am

Nonstop2h 45m

$79

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 12/4

11:15 am-1:11 pm

Nonstop2h 56m

$79

TampaChicago

TPA - ORD

TPAORD

Tampa

Tue 12/31

10:36 am-12:46 pm

Nonstop3h 10m

$46

TampaChicago

TPA - ORD

TPAORD

Tampa

Tue 1/7

7:02 pm-7:19 pm

2 stops25h 17m

$93

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 12/14

6:35 pm-10:06 pm

1 stop4h 31m

$98

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 11/27

7:40 pm-8:21 am

1 stop13h 41m

$130

TampaChicago

TPA - ORD

TPAORD

Tampa

Fri 3/7

10:14 pm-8:22 am

1 stop11h 08m

$166

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 2/8

8:00 am-1:42 pm

1 stop6h 42m

$98

Flights are sorted by cheapest first

Deals found on 11/4

Showing 1-10 of 26 results
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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.

Travel insights for flights from Clearwater to Chicago

Get recent, data-driven insights about flights from Clearwater to Chicago including ideal travel times, pricing trends, and more.

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 November 1, 2024.

To ensure you get the cheapest price possible for a flight from Clearwater to Chicago, you should look to book at least 89 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.

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What is the cheapest month to book a flight from Clearwater to Chicago?

Currently, September is the cheapest month in which you can book a flight from Clearwater to Chicago (average of $232). Flying from Clearwater to Chicago in June is currently the most expensive (average of $308). 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 November 4, 2024.

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 November 3, 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. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Find deals

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 November 4, 2024.

The most flights from CL9 to CHI are scheduled on a Monday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 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 November 4, 2024.
To help decide which airline to fly from Clearwater to Chicago, see what other customers have to say about Spirit Airlines, Frontier and United Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
5,089 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,829 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Porter Airlines
7.7
Good
293 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

JetBlue
7.5
Good
3,493 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

United Airlines
7.4
Good
9,226 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

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.

  • Can I find flights from Clearwater to Chicago for under $100 on Cheapflights?

    Yes, there are multiple flights from Clearwater to Chicago for under $100. The cheapest flight booked recently is on Frontier for just $78, but on average you can expect to pay $167.

  • Are there nonstop flights from Clearwater to Chicago for under $100 on Cheapflights?

    Cheapflights has at least 7 direct flights from Clearwater to Chicago under $100. A good price for a nonstop flight from Clearwater to Chicago is less than $123.

  • Are there last-minute flights available from Clearwater to Chicago for under $200?

    There are currently 13+ open flights from Clearwater to Chicago within the next 7 days for less than $200.

  • What days are nonstop flights available from Clearwater to Chicago?

    Days when nonstop flights are available for this flight are: Monday, Tuesday, Wednesday, Thursday, Friday, Saturday.

  • How many flights depart from Clearwater to Chicago on average per day?

    On average, you can expect to see 27 flights from Clearwater to Chicago a day.
    Morning (6am - Noon) - 56% of flight departures
    Afternoon (Noon - 6pm) - 22% of flight departures
    Evening (6pm - Midnight) - 22% of flight departures

  • How long is the flight from Clearwater to Chicago?

    For as low as $78, Frontier can have you in Chicago from Clearwater in 2h 47m. There are 1011 mi between Clearwater and Chicago. Generally, flights for this route are nonstop.

  • 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 ($38), Spirit Airlines ($51), 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: Southwest (100%), Japan Airlines (93%), SWISS (90%).

  • What are the cheapest flights from Clearwater to Chicago?

    Looking at all options, your cheapest flight can be booked for $79. While the most popular route (Tampa - Chicago O'Hare Intl) can be booked for $82 on average our data indicates $891 when flying from Clearwater to Chicago.

  • What does MCO to ORD mean?

    This is defined as Orlando Airport (MCO) and Chicago O'Hare Intl Airport (ORD). Codes like Chicago O'Hare Intl Airport are often used to just call airports uniquely. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Clearwater to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Clearwater to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Clearwater to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Clearwater to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Clearwater to Chicago that allow pets onboard?

    Many airlines flying from Clearwater to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Clearwater to Chicago?

    Yes, you can often find last-minute deals on Clearwater to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Clearwater to Chicago flight deals updated?

    The Clearwater to Chicago flight deals you see on this page were last updated on 11/4.

  • What is the cheapest month to book a flight from Clearwater to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Clearwater to Chicago (average of $232). Flying from Clearwater to Chicago in June is currently the most expensive (average of $308). 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

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Alternative routes for Clearwater to Chicago

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 2,455,398 searches. Data last updated November 4, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$49Average$145FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$59Average$151FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$92Average$203FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$138Average$285FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$151Average$332FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$155Average$326FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$387FlexibilityNo cancel feeOn-timeN/A
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