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

Featured airlines

American Airlines
United
Southwest Airlines
Delta
Spirit Airlines
JetBlue Airways
Frontier Airlines
Air India
Hawaiian Airlines

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key
Find available prices by choosing your travel dates.
Flights from Chicago (MDW) to Clearwater (CLW)
Origin airport
Midway Intl.
Destination airport
Clearwater Air Park
Distance
994 mi

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.

Frequently asked questions

Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Clearwater Air Park Airport (CLW) last minute?
When it’s time to book your flights, being prepared pays dividends. While you could pick up a last-minute deal on a Midway Intl. Airport (MDW) to CLW flight, prices usually don’t get cheaper as the date of departure nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to lock in a domestic flight is between 28 – 35 days in advance. For international trips it’s three to four months.
What airports do you fly into for Clearwater from Chicago?
With Clearwater Air Park Airport (CLW), St. Petersburg-Clearwater Intl. Airport (PIE) and Tampa Intl. Airport (TPA) to pick from, making your way from Chicago to Clearwater is no sweat. The city’s key hub, Clearwater Air Park Airport (CLW), is about 3 mi east of the downtown area. Apart from the price of fares, consider things like the ease of getting from the airport and the distance to your hotel before deciding where you’ll get off the plane. Get your Clearwater adventure off on the right foot by visiting Clearwater Marine Aquarium and Pier 60 Park.
Can I change the date of my flight from Chicago Airport to CLW?
We know plans can get upended, so Expedia is here to help make amending your journey easy. To start, access your Chicago Airport to Clearwater Air Park Airport (CLW) itinerary through the Expedia Trips portal and browse the fare conditions and rules to see if you can make changes. If you booked your fare in the last 24 hours, some airlines allow you to cancel at no cost and book new flights. If you booked more than 24 hours ago, contact us via our Customer Service portal to find out your options.

Explore a world of travel with Expedia

*Available to One Key members.