Cheap flights from Clearwater Beach to Chicago (CHI)

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

The best prices from Clearwater Beach to Chicago are usually found in September or October, booked 41 days in advance, depart on a Saturday or Thursday and return on a Tuesday

How to find the cheapest flight from
Clearwater Beach to Chicago (CHI)

All the information you need to plan the best null to CHI flight in 2022: compare Clearwater Beach to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
CW9 - CHI
Price
$97 - $276
CHI
Temperature
23 - 73.4 °F
CHI
Rainfall
1.7 - 4.9 inches

Popular in

June

High demand for flights, 36% potential price rise

Cheapest in

September

Best time to find cheap flights, 45% potential price drop

Round-trip from

$97

From Clearwater Beach to Chicago (CHI)

One-way from

$59

One-way flight from Clearwater Beach to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest month to fly from Clearwater Beach to Chicago?

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, September can be a great choice for travel to Chicago. Flights to Chicago from Clearwater Beach in September are about $177 on average during September, but can be found for as low as $49.

How far in advance should I book a flight from Clearwater Beach to Chicago?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 36 days in advance, which can save you up to 39% on flights from Clearwater Beach to Chicago compared to booking the week you need them. Waiting 36 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $181. For sooner than that we have options available in the next 3 days from $248.

When is the cheapest time to fly from Clearwater Beach to Chicago (CW9 - CHI)?

When flying from Clearwater Beach 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.

Cheap flights from Clearwater Beach to Chicago in August, September 2022

The best prices found for Clearwater Beach to CHI flights for August, September
16 Aug - 17 Aug
$54pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa
17 Aug - 31 Aug
$59pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa
17 Aug - 23 Aug
$60pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa

Clearwater Beach to Chicago 2022 flight deals

Cheap flights to Chicago from Clearwater Beach found for this year
16 Aug - 17 Aug
$54pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa
17 Aug - 31 Aug
$59pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa
17 Aug - 23 Aug
$60pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa

Cheap Spirit Airlines flights from Clearwater Beach to Chicago

3 Sep - 7 Sep
$67pp
TPA
Tampa
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
TPA
Tampa
30 Aug - 3 Sep
$70pp
TPA
Tampa
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
TPA
Tampa
3 Sep - 4 Sep
$75pp
TPA
Tampa
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
TPA
Tampa

Cheap Frontier flights from Clearwater Beach to Chicago

23 Aug - 24 Aug
$54pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa
18 Aug - 30 Aug
$59pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa
27 Aug - 29 Aug
$60pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa

Non-stop flights to Chicago from Clearwater Beach

Save time with Clearwater Beach to Chicago direct flight deals
23 Aug - 24 Aug
$54pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa
27 Aug - 29 Aug
$60pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa
23 Aug - 27 Aug
$64pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa

Last minute flights from Clearwater Beach to Chicago

Late deals on round-trip flights to Chicago from Clearwater Beach, departing today and this week
16 Aug - 17 Aug
$54pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa
17 Aug - 31 Aug
$59pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa
17 Aug - 23 Aug
$60pp
TPA
Tampa
Frontier
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
Non-Stop
TPA
Tampa

One-way flights to Chicago from Clearwater Beach

The cheapest one-way flights from Clearwater Beach to Chicago
3:50 pm - 2:38 am
Multiple Airlines
2 Stops
11h 48m
TPA - MDW
Multiple Airlines
$59
Kiwi.com
5:00 am - 6:38 am
Frontier
Nonstop
2h 38m
TPA - MDW
Frontier
$61
Kiwi.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Clearwater Beach</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Clearwater Beach to Chicago

Which airlines flying from Clearwater Beach to Chicago have flexible cancellations due to COVID-19?

Spirit Airlines, United Airlines, and American Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

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

Yes, there are multiple flights from Clearwater Beach to Chicago for under $100. The cheapest flight booked recently is on Frontier for just $54, but on average you can expect to pay $70.

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

Cheapflights has at least 20 direct flights from Clearwater Beach to Chicago under $100. A good price for a nonstop flight from Clearwater Beach to Chicago is less than $72.

Are there last-minute flights available from Clearwater Beach to Chicago for under $100?

There are currently 20+ open flights from Clearwater Beach to Chicago within the next 7 days for less than $100.

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

You can find nonstop flights on the following days: Sunday, Saturday.

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

8 flight departures from Clearwater Beach to Chicago per day on average.
Morning (6am - Noon) - 25% of flight departures
Afternoon (Noon - 6pm) - 75% of flight departures

How long is the flight from Clearwater Beach to Chicago?

Departing from Clearwater Beach to Chicago will take you 2h 35m. Clearwater Beach and Chicago are separated by a distance of 1011 mi. Most flights are nonstop.

What are the cheapest flights from Clearwater Beach to Chicago?

On average you can expect to pay $494 for a flight from Clearwater Beach to Chicago. The cheapest flight overall is $70 while the most popular route, (Tampa - Chicago O'Hare Intl) is currently priced at $67.

What are the most popular airlines that fly from Clearwater Beach to Chicago?

Consider Undisclosed Carrier, American Airlines or Alaska Airlines when booking your flight. These represent the most popular airlines when flying from Clearwater Beach to Chicago.

What are the most reliable airlines from Clearwater Beach to Chicago?

No one likes to see their flight delayed. When booking a flight from Clearwater Beach to Chicago consider choosing ANA (90%), Austrian Airlines (90%) or Brussels Airlines (90%) as they are the most reliable in getting you off to your destination on time.

What are the most popular routes from Clearwater Beach to Chicago?

When deciding which route to take from Clearwater Beach to Chicago consider Tampa - Chicago O'Hare Intl, Tampa - Chicago Midway or Tampa - Chicago Greater Rockford as they are the most popular.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Clearwater Beach?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from Clearwater Beach need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Clearwater Beach are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago.

Quarantine requirements
Visitors from Clearwater Beach are not required to quarantine after entering Chicago.

Do I need a test to fly back to Clearwater Beach from Chicago?

Returning to Clearwater Beach from Chicago

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering Clearwater Beach.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Clearwater Beach.

Hide COVID Travel Restrictions for Chicago, IL

Alternative routes for Clearwater Beach to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 7 airlines flying from Clearwater Beach to Chicago

The chart below displays the airlines Cheapflights users traveling from Clearwater Beach to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Juneyao Airlines
$12 $22 No cancel fee 66%

We couldn't confirm the COVID-19 safety measures taken by Juneyao Airlines. Please check directly on their website for additional information.

Frontier
$23 $188 No cancel fee 62%
Spirit Airlines
$43 $157 No cancel fee 65%
United Airlines
$58 $248 No cancel fee 69%
American Airlines
$63 $302 No cancel fee 71%
Allegiant Air
$72 $238 No cancel fee 88%
Delta
$81 $373 No cancel fee N/A

Hourly flight availability from Clearwater Beach to Chicago

See what time of day planes typically take off from Clearwater Beach towards Chicago.
Morning 6 AM to noon 53% of Clearwater Beach to CHI departures
Afternoon Noon to 6 PM 34% of Clearwater Beach to CHI departures
Evening 6 PM to midnight 7% of Clearwater Beach to CHI departures
Early morning Midnight to 6 AM 6% of Clearwater Beach to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Clearwater Beach to Chicago
See how many times per day planes take to the skies headed from Clearwater Beach to Chicago.
Sunday
53 daily flights
Monday
53 daily flights
Tuesday
49 daily flights
Wednesday
52 daily flights
Thursday
52 daily flights
Friday
52 daily flights
Saturday
46 daily flights
Home Flights North America USA Illinois Chicago Cheap flights from Clearwater Beach to Chicago