flight
AirlinesHotels
🇺🇸

English

Login
UP TO 10% OFF
FURTHER REDUCTIONS • AIRLINES RESERVATION

Tap to call our agents for exclusive fares. 24/7 assistance.

Call (888) 319-6206

Flights from Clearwater to Chicago from $55

Explore flight options from Clearwater to Chicago with competitive pricing starting from $278.
Clearwater

PIE

→

Chicago

RFD

11/05/2025 – 11/12/2025

Cheap flight deals from Clearwater to Chicago

Average price start from:
i

$103

Round-trip flights from Clearwater to Chicago starting at $103. Book now for the best deals!

One-way from:
i

$55

One-way flights from Clearwater to Chicago starting at $55. Great for flexible travel!

Cheapest day:
i

Thursday

Thursday is the cheapest day to fly from Clearwater to Chicago. Save more by booking on this day!

Cheapest In:
i

$76

Jun 2025

Jun 2025 is the cheapest month to fly from Clearwater to Chicago with prices starting at $76.

Find flight deals from Clearwater to Chicago

Cheapest flights from Clearwater to Chicago

ONEWAY FLIGHTS

LAST MINUTE

CHEAP FLIGHTS

BEST FLIGHTS

Explore the cheapest oneway flights from Clearwater to Chicago spotted daily.

PIE

Clearwater

PIE - Clearwater • 2025-11-05 • 09:00

Unknown

60 min

RFD

Unknown City

$55

Non-stop • 60 min

SFB

Clearwater

SFB - Clearwater • 2025-11-05 • 09:00

Unknown

60 min

RFD

Unknown City

$57

Non-stop • 60 min

PGD

Clearwater

PGD - Clearwater • 2025-11-05 • 09:00

Unknown

60 min

RFD

Unknown City

$157

Non-stop • 60 min

PIE

Clearwater

PIE - Clearwater • 2025-11-05 • 09:00

Unknown

60 min

RFD

Unknown City

$228

Non-stop • 60 min

PGD

Clearwater

PGD - Clearwater • 2025-11-05 • 09:00

Unknown

60 min

RFD

Unknown City

$362

Non-stop • 60 min

Price Trends & Analysis

Monthly Price Trends

The cheapest month for flights from Clearwater to Chicago is May.

Weather & Climate Information

Temperature

Chicago experiences a humid continental climate, with cold winters averaging 20°F (-6°C) and warm summers averaging 80°F (27°C). The best times for comfortable travel are during late spring (May) and early fall (September-October), when temperatures are mild and rainfall is less frequent.

Rainfall

The best time to visit Chicago is during late spring (May to early June) or early fall (September to October) when the weather is mild and pleasant. These periods also feature fewer tourists and vibrant local events like the Chicago Blues Festival in June and the Chicago Gourmet in September, enhancing your experience.

Airlines at RFD

Experience seamless travel from Clearwater to Chicago with trusted airlines like Allegiant Air. These carriers ensure reliable connections and flexible scheduling options for travelers. Flight duration typically ranges around 10-15 hours, with most routes including one stopover in major aviation hubs. For your trip from Clearwater to Chicago, these airlines offer modern amenities and professional service to make your journey comfortable and enjoyable.

Places to Visit in Chicago

Chicago, the Windy City, captivates with its stunning skyline, where modern architecture meets historic charm along the shores of Lake Michigan. Visitors can immerse themselves in the vibrant arts scene, from world-class museums like the Art Institute to the soulful rhythm of blues clubs. Stroll through Millennium Park, savor deep-dish pizza, and take in the city’s rich history, including the storied tales of the Great Chicago Fire and Prohibition, making every moment in this dynamic metropolis a thrilling adventure.

About Chicago

Explore the wonders of Chicago on your journey from Clearwater. This remarkable destination blends cultural treasures with modern amenities, creating an enriching travel experience. Consider visiting during off-peak seasons for better value and fewer crowds.

Airlines Flying from Clearwater to Chicago

Experience seamless travel from Clearwater to Chicago with trusted airlines like Allegiant Air. These carriers ensure reliable connections and flexible scheduling options for travelers. Flight duration typically ranges around 10-15 hours, with most routes including one stopover in major aviation hubs. For your trip from Clearwater to Chicago, these airlines offer modern amenities and professional service to make your journey comfortable and enjoyable.

Hotels in Chicago

For convenient stays near Chicago, consider these hotels close to RFD Airport. These properties ensure easy access to RFD Airport while offering comfortable accommodations. Many provide complimentary shuttle services for seamless airport transfers.
Hotel

Hotel

Category: Standard

Comfortable accommodations with modern amenities.

Location: Near airport

Hotel ID:

About Chicago

Explore the wonders of Chicago on your journey from Clearwater. This remarkable destination blends cultural treasures with modern amenities, creating an enriching travel experience. Consider visiting during off-peak seasons for better value and fewer crowds.

Places to Visit in Chicago

Chicago, the Windy City, captivates with its stunning skyline, where modern architecture meets historic charm along the shores of Lake Michigan. Visitors can immerse themselves in the vibrant arts scene, from world-class museums like the Art Institute to the soulful rhythm of blues clubs. Stroll through Millennium Park, savor deep-dish pizza, and take in the city’s rich history, including the storied tales of the Great Chicago Fire and Prohibition, making every moment in this dynamic metropolis a thrilling adventure.

Hotels in Chicago

For convenient stays near Chicago, consider these hotels close to RFD Airport. These properties ensure easy access to RFD Airport while offering comfortable accommodations. Many provide complimentary shuttle services for seamless airport transfers.
Hotel

Hotel

Category: Standard

Comfortable accommodations with modern amenities.

Location: Near airport

Hotel ID:

Airlines Flying from Clearwater to Chicago

Experience seamless travel from Clearwater to Chicago with trusted airlines like Allegiant Air. These carriers ensure reliable connections and flexible scheduling options for travelers. Flight duration typically ranges around 10-15 hours, with most routes including one stopover in major aviation hubs. For your trip from Clearwater to Chicago, these airlines offer modern amenities and professional service to make your journey comfortable and enjoyable.

Frequently Asked Questions

What's the best deal for flights from Clearwater to Chicago?

The lowest fare available is $55. Maximize savings by booking during May and selecting Thursday flights.

How many hours does it take to fly from Clearwater to Chicago?

Flight duration typically ranges around 10-15 hours, with most flights including one stopover for optimal route efficiency.

Which carriers fly between Clearwater and Chicago?

Major airlines serving this route include Allegiant Air. Each offers different schedules and amenities to suit various travel preferences.

What's the ideal booking window for this route?

Book 2-3 months in advance for the best prices. Traveling during May can provide additional savings opportunities.

Are there convenient hotels near RFD Airport?

Yes, RFD Airport is surrounded by hotels offering shuttle services and modern amenities for travelers.

Why should I visit Chicago?

Chicago offers an incredible mix of cultural experiences and modern attractions. Plan your visit during pleasant weather months for the most enjoyable experience.

flight

Helps you find the cheapest flight deals to any destination with ease.

Browse through the best hotels and find exclusive deals.

About

About Us

Android App

iOS App

Blog

Explore

Flights

Hotels

More

Customer Support

Terms & Conditions

Privacy Policy

Refund Policy

Sitemap

© 2018-2025 AirlinesMap Inc. All rights reserved.

Disclaimer & TCPA Consent — By providing your phone number, you consent to receive calls and text messages (including automated or pre-recorded messages) from AirlinesMap.com, its affiliates, and partners at the number provided. Message and data rates may apply. You can opt out anytime by replying “STOP” or calling (888) 319-6206.AirlinesMap.com is an independent travel information platform and is not affiliated with any airline. Flight data, fares, and schedules are provided by third-party sources and may change without notice. AirlinesMap.com does not guarantee accuracy or availability and does not handle bookings directly. Use of this site signifies your agreement to these terms.