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

Popular airlines from Chicago Midway Airport (MDW) to Clearwater, FL (CLW-Clearwater Air Park)

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Alternative airports near Clearwater

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Tampa Intl. TPA. Cheapest option available. Average driving time to city center is 34 minutes. Flights from $283
TPA
Tampa Intl.
Cheapest
Average driving time to city center34 min
Flights from $283

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Clearwater Air Park Airport (CLW) cost?
Lock in a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Clearwater Air Park Airport (CLW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Clearwater Air Park Airport (CLW)?
is the least expensive month to fly from MDW to CLW. Timing your trip outside of the busy season is often the key to finding better fares.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Clearwater Air Park Airport (CLW)?
To find the cheapest airline that'll fly you from MDW to CLW, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Midway Intl. Airport (MDW) to Clearwater Air Park Airport (CLW)?
You'll need to take a flight with a layover when traveling from Midway Intl. Airport (MDW) to Clearwater Air Park Airport (CLW). Direct flights don't operate daily on this route. However, just filter your search to include one or two stops to discover an option that works for you.
What day of the week has the most flights from MDW to CLW?
Generally you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can change based on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Clearwater Air Park Airport (CLW)?
Opt for a flight from Midway Intl. Airport (MDW) to Clearwater Air Park Airport (CLW) that leaves before 3 PM to reduce the risk of cancellations. Departures later than this have a 22% higher chance of being canceled, on average.**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 Midway Intl. Airport (MDW) to Clearwater Air Park Airport (CLW) last-minute?
Waiting until just before your trip to book a ticket from MDW to CLW generally means paying more. While it's possible to find some last-minute discounts, there's no guarantee. Be flexible with your itinerary to maximize your chances of getting a bargain.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Clearwater Air Park Airport (CLW)?
Usually, it's possible to reschedule or cancel your MDW to CLW flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Clearwater Air Park
Distance
994 mi

Book with confidence

Chicago to Clearwater Flights

The cheapest times to fly from Chicago to Clearwater

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 Chicago to Clearwater are during the month of . You can find some of the cheapest flights from Chicago to Clearwater with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Clearwater

Sunday is one of the best days to book for cheap flights from Chicago to Clearwater: 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 Chicago to Clearwater

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 Chicago to Clearwater 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 Chicago to Clearwater 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 Chicago to Clearwater 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.

 

Chicago to Clearwater Flights

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*Available to One Key members.