Cheap Flights from Clearwater (CLW) to Chicago (ORD)

Popular airlines from Clearwater, FL (CLW-Clearwater Air Park) to Chicago O'Hare Intl. Airport (ORD)

Frequently asked questions

How much does a flight from Clearwater Air Park Airport (CLW) to O'Hare Intl. Airport (ORD) cost?
Grab a cheap one-way flight or cheap return flight from Clearwater Air Park Airport (CLW) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Clearwater Air Park Airport (CLW) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from CLW to ORD is , when there's less demand. Off-peak months are usually when airlines offer lower prices between these airports.
Which airlines fly direct from Clearwater Air Park Airport (CLW) to O'Hare Intl. Airport (ORD)?
While Clearwater, FL (CLW-Clearwater Air Park) doesn't offer any direct flights to O'Hare Intl. Airport (ORD), other airports have nonstop options. Taking off from Tampa Intl. Airport (TPA) will get you to Chicago without any detours.
What is the cheapest airline that flies from Clearwater Air Park Airport (CLW) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest CLW to ORD flight.
How many flights per day from Clearwater Air Park Airport (CLW) to O'Hare Intl. Airport (ORD)?
There aren't any daily direct flights available from Clearwater Air Park Airport (CLW) to O'Hare Intl. Airport (ORD). But you can book flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from CLW to ORD?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can change based on various factors, such as the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Clearwater Air Park Airport (CLW) to O'Hare Intl. Airport (ORD)?
Book a flight from Clearwater Air Park Airport (CLW) to O'Hare Intl. Airport (ORD) that takes off before 3 PM to reduce the risk of cancellations and delays. Later departures are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Clearwater Air Park Airport (CLW) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from CLW to ORD are usually more expensive. To lock in the lowest rates, start searching for flights well ahead of time. That being said, if you're flexible with your travel dates, you may land a cheap ticket right before your trip.
Is it cheaper to book a CLW to ORD flight and hotel package?
You'll typically save money by securing a CLW to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. After selecting your ideal accommodations and flights, consider adding extras like car rentals, tours and activities.
Can I cancel or change the date of my flight from Clearwater Air Park Airport (CLW) to O'Hare Intl. Airport (ORD)?
If you reserved your CLW to ORD flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.

Travel information

Travel information

Origin airport
Clearwater Air Park
Destination airport
O'Hare Intl.
Distance
1009 mi

Book with confidence

Book with confidence

Clearwater to Chicago Flights

The cheapest times to fly from Clearwater to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Clearwater to Chicago are during the month of . You can find some of the cheapest flights from Clearwater to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Clearwater to Chicago

Sunday is one of the best days to book for cheap flights from Clearwater to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Clearwater to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Clearwater to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Clearwater to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Clearwater to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Clearwater to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.