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$52+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
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 Saturday or Friday 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 20, 2024.

Popular in

October

Cheapest in

February

Round-trip from

$104
(Cheapflightsfares)

One-way from

$52
(Cheapflightsfares)
High demand for flights, 20% potential price rise
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Best time to find cheap flights, 30% 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 20, 2024.

This Frontier deal was found by Cheapflights users on 11/20. 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.
Tue 12/178:56 amTPA - ORD
1 stop8h 37mFrontier
Wed 12/1810:22 pmORD - TPA
1 stop8h 31mFrontier
Deal found 11/20$106
This Frontier deal was found by Cheapflights users on 11/19. 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.
Tue 12/178:46 pmTPA - MDW
Nonstop2h 47mFrontier
Wed 12/186:50 amMDW - TPA
Nonstop2h 46mFrontier
Deal found 11/19$108
This Kiwi.com deal was found by Cheapflights users on 11/19. 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.
Sat 12/147:35 amTPA - ORD
Nonstop3h 03mMultiple Airlines
Wed 12/1810:22 pmORD - TPA
1 stop8h 31mMultiple Airlines
Deal found 11/19$113
This Cheapflightsfares deal was found by Cheapflights users on 11/20. 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 12/147:35 amTPA - ORD
Nonstop3h 03mSpirit Airlines
Mon 12/1611:25 amORD - TPA
Nonstop2h 50mSpirit Airlines
Deal found 11/20$114
This Delta deal was found by Cheapflights users on 11/19. 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 12/146:35 pmTPA - MDW
1 stop4h 31mDelta
Tue 1/75:07 pmMDW - TPA
1 stop6h 19mDelta
Deal found 11/19$196
This Delta deal was found by Cheapflights users on 11/19. 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 12/141:52 pmTPA - ORD
1 stop6h 37mDelta
Wed 1/87:05 amORD - TPA
1 stop4h 25mDelta
Deal found 11/19$196
This KAYAK deal was found by Cheapflights users on 11/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/117:10 pmTPA - MDW
Nonstop2h 40mSouthwest
Mon 12/169:25 amMDW - TPA
Nonstop2h 35mSouthwest
Deal found 11/19$214
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Thu 12/124:30 pmTPA - ORD
Nonstop2h 57mUnited Airlines
Sun 12/157:30 amORD - TPA
Nonstop2h 49mUnited Airlines
Deal found 11/19$214
This eDestinos deal was found by Cheapflights users on 11/19. 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.
Mon 12/309:35 amTPA - MDW
2 stops28h 34mMultiple Airlines
Thu 1/27:17 amMDW - TPA
1 stop9h 32mMultiple Airlines
Deal found 11/19$225
This KAYAK deal was found by Cheapflights users on 11/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1711:25 amTPA - ORD
1 stop11h 35mSouthwest
Wed 12/185:45 amORD - TPA
2 stops13h 45mSouthwest
Deal found 11/20$237
This American Airlines deal was found by Cheapflights users on 11/19. 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 12/48:36 amTPA - ORD
Nonstop3h 00mAmerican Airlines
Sun 12/88:26 amORD - TPA
Nonstop2h 40mAmerican Airlines
Deal found 11/19$248
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Sat 11/234:17 pmTPA - RFD
2 stops21h 41mMultiple Airlines
Sun 12/84:11 pmRFD - TPA
3 stops26h 19mMultiple Airlines
Deal found 11/19$572

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TampaChicago

TPA - ORD

TPAORD

Tampa

Tue 12/17

8:56 am-4:33 pm

1 stop8h 37m

Chicago O'Hare Intl

Wed 12/18

10:22 pm-7:53 am

1 stop8h 31m

$104

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 2/15

9:08 pm-11:00 pm

Nonstop2h 52m

Chicago Midway

Sat 2/22

4:30 pm-8:13 pm

Nonstop2h 43m

$106

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 12/14

7:35 am-9:38 am

Nonstop3h 03m

Chicago O'Hare Intl

Wed 12/18

10:22 pm-7:53 am

1 stop8h 31m

$113

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 12/14

7:35 am-9:38 am

Nonstop3h 03m

Chicago O'Hare Intl

Mon 12/16

11:25 am-3:15 pm

Nonstop2h 50m

$114

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 1/23

7:15 am-9:05 am

Nonstop2h 50m

Chicago Midway

Sun 1/26

6:20 pm-9:55 pm

Nonstop2h 35m

$184

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 12/14

6:35 pm-10:06 pm

1 stop4h 31m

Chicago Midway

Tue 1/7

5:07 pm-12:26 am

1 stop6h 19m

$196

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 12/14

1:52 pm-7:29 pm

1 stop6h 37m

Chicago O'Hare Intl

Wed 1/8

7:05 am-12:30 pm

1 stop4h 25m

$196

TampaChicago

TPA - ORD

TPAORD

Tampa

Thu 12/12

4:30 pm-6:27 pm

Nonstop2h 57m

Chicago O'Hare Intl

Sun 12/15

7:30 am-11:19 am

Nonstop2h 49m

$214

TampaChicago

TPA - MDW

TPAMDW

Tampa

Mon 12/30

9:35 am-1:09 pm

2 stops28h 34m

Chicago Midway

Thu 1/2

7:17 am-5:49 pm

1 stop9h 32m

$225

TampaChicago

TPA - ORD

TPAORD

Tampa

Tue 1/21

7:55 am-5:18 pm

1 stop10h 23m

Chicago O'Hare Intl

Mon 1/27

7:00 am-3:27 pm

1 stop7h 27m

$226

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 28 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.

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 15, 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.

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 20, 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 18, 2024.

Travelers seeking maximum savings on their Clearwater to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Monday afternoons 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 November 20, 2024.

The most flights from CL9 to CHI are scheduled on a Monday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (23 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 20, 2024.
To help decide which airline to fly from Clearwater to Chicago, see what other customers have to say about Spirit Airlines, American Airlines and Southwest. 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
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

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
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

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
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Porter Airlines
7.8
Good
288 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

JetBlue
7.5
Good
3,394 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

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
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

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.

  • 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 ($52), Spirit Airlines ($56), 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%), ANA (90%).

  • What are the cheapest flights from Clearwater to Chicago?

    Looking at all options, your cheapest flight can be booked for $57. While the most popular route (Tampa - Chicago O'Hare Intl) can be booked for $109 on average our data indicates $930 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, 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$49Average$153FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$56Average$154FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$92Average$191FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$138Average$286FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$153Average$336FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$155Average$350FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$489FlexibilityNo cancel feeOn-timeN/A
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