$38 Find Cheap Flights from Chicago to Clearwater Beach

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Clearwater Beach departing on 9/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights from Chicago to Clearwater Beach

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Clearwater Beach (CHI-TPA)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Clearwater Beach that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Clearwater Beach

Fri, Sep 5 - Sun, Sep 7
Frontier Logo
6:21 am - 9:57 amMDW-TPA
2h 36mnonstop
Frontier Logo
10:55 am - 12:44 pmTPA-MDW
2h 49mnonstop
$73Frontier
Find Deal
Fri, Sep 12 - Sun, Sep 14
Frontier Logo
6:21 am - 9:57 amMDW-TPA
2h 36mnonstop
Frontier Logo
10:55 am - 12:44 pmTPA-MDW
2h 49mnonstop
$74Frontier
Find Deal
Sun, Oct 19 - Sun, Oct 26
Frontier Logo
5:20 am - 8:55 amMDW-TPA
2h 35mnonstop
Frontier Logo
9:57 am - 11:44 amTPA-MDW
2h 47mnonstop
$76Frontier
Find Deal
Thu, Sep 11 - Sun, Sep 14
Frontier Logo
8:05 am - 12:05 pmORD-TPA
3h 00mnonstop
Frontier Logo
5:01 am - 7:10 amTPA-ORD
3h 09mnonstop
$78Frontier
Find Deal
Sun, Aug 31 - Thu, Sep 4
Frontier Logo
6:10 am - 10:02 amORD-TPA
2h 52mnonstop
Frontier Logo
5:01 am - 7:10 amTPA-ORD
3h 09mnonstop
$79Frontier
Find Deal
Thu, Sep 25 - Sun, Sep 28
Frontier Logo
8:05 am - 12:05 pmORD-TPA
3h 00mnonstop
Frontier Logo
5:01 am - 7:10 amTPA-ORD
3h 09mnonstop
$80Frontier
Find Deal
Wed, Sep 10 - Wed, Sep 17
Spirit Airlines Logo
5:46 pm - 9:31 pmORD-TPA
2h 45mnonstop
Spirit Airlines Logo
8:15 am - 10:18 amTPA-ORD
3h 03mnonstop
$85Spirit Airlines
Find Deal
Wed, Sep 3 - Wed, Sep 10
Spirit Airlines Logo
5:21 pm - 8:55 pmORD-TPA
2h 34mnonstop
Spirit Airlines Logo
8:15 am - 10:18 amTPA-ORD
3h 03mnonstop
$87Spirit Airlines
Find Deal
Tue, Sep 9 - Sat, Sep 20
Spirit Airlines Logo
5:46 pm - 9:31 pmORD-TPA
2h 45mnonstop
Spirit Airlines Logo
8:14 am - 10:17 amTPA-ORD
3h 03mnonstop
$88Spirit Airlines
Find Deal
Thu, Sep 4 - Tue, Sep 9
 Logo
8:05 am - 12:05 pmORD-TPA
3h 00mnonstop
 Logo
8:15 am - 10:18 amTPA-ORD
3h 03mnonstop
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$38
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 28% increase in price.
Flight from Chicago Midway Airport to Tampa

When to book flights from Chicago to Clearwater Beach

Are your dates flexible? Find out the best times to travel from Chicago to Clearwater Beach based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Flights from Chicago to Clearwater Beach: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew the route from Chicago to Clearwater Beach 
Verified travelerFlew with American AirlinesORD-TPADec 2024
I recommend having movies and songs downloaded on your device.
AyannaFlew with Spirit AirlinesORD-TPAMay 2024
Fly out of Midway airport instead of O'Hare because its smaller and easier to manage.

FAQs for booking flights from Chicago to Clearwater Beach

  • Which airports will I be using when flying from Chicago to Clearwater Beach?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway, Chicago O'Hare Intl or Chicago Greater Rockford. Clearwater Beach does not have its own airport so you’ll be flying into nearby Tampa airport, which is 18.0 mi away.

  • How long does a flight from Chicago to Clearwater Beach take?

    Direct flights cover the 1,002 miles separating Chicago and Clearwater Beach in about 2h 34m.

  • How many flights are there between Chicago and Clearwater Beach?

    40 direct flights run between Chicago and Clearwater Beach on a daily basis. On average, there are about 281 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Clearwater Beach?

    Consider leaving on a Friday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Sundays.

  • How does KAYAK find such low prices on flights from Chicago to Clearwater Beach?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Clearwater Beach.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Clearwater Beach?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Clearwater Beach from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Clearwater Beach?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Clearwater Beach with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Clearwater Beach?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Clearwater Beach from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Clearwater Beach?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Clearwater Beach found on KAYAK was with Frontier for $38. Frontier offered a round-trip connection from $73 and Spirit Airlines from $85.

Top tips for finding cheap flights from Chicago to Clearwater Beach

  • There is no airport in Clearwater Beach. Instead, you’ll be flying into Tampa Airport when flying between Chicago and Clearwater Beach.
  • The cheapest flight from Chicago to Clearwater Beach was found 82 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is September.

Reviews of the top 5 airlines serving Chicago to Clearwater Beach

 
Need help choosing which airline to fly with from Chicago to Clearwater Beach? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4244 reviews
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
8.0Comfort
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

My experience with Spirit was good, but the experience with Kayak was not. Based on the Spirit agent Kayak added an additional charge after purchasing the tickets. When I buy the tickets I paid the total amount and I only pay once. This time they added an additional charge because based on Spirit they partially charge the tickets and I still needed to pay a second time. This is not good at all and Unprofessional

Spirit gets such a bad rap. I have never had a bad experience with them and the crew is always friendly and funny. This trip I had knee replacement surgery surgery 10 weeks ago. It is still a little rough to get get from point a to point b. And Spirit was on top of it. When there was a seat available the stewardess asked me if I wanted to move to an open seat so I could elevate my leg on the empty seat? 5 stars all around. They helped me on and helped me off the plane. I can’t say enough about the crew!!

This gate agents are always so rude! I stopped flirting with spirit years ago for that reason I thought it would change by now. It’s so tacky they try to treat you like a school child i hate it

The staff was very sarcastic, the flight was delayed. There was no wi-fi o any type of entertainment. The plane was dirty and we have to wait a long time for the luggage to come out.

Booked through kayak, everything seemed normal but when it came time to go, my flight ticket didn’t exist, so I had to purchase another set of tickets at the airport the day of the flight, for about double. When I reached kayaks customer service, they claimed no responsibility, and pushed me onto another 3rd party booking service, airfare assist, where I have had no luck getting any kind of help or refund. I’ve used kayak many times, but I’ll never again after I’ve been burned by this.

The air fares are good, Charging me for every single thing 😩

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

I am very happy with my experience with Spirit Airlines. Both flights were on time. Boarding was very pleasant. Crew was very nice. Flights were amazing and we even arrived earlier than the schedule time. I am hoping Spirits keeps on having non stop flight from Ft Lauderdale to Hartford for many years to come.

you guys canceled my flight last minute and lost my luggage.

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

It was a no frills flight. Would have liked to be able to charge my device

Seats were extremely uncomfortable and it was very hot on the plane.

Since they are a budget airline, I wasn’t expecting too much but they did some things well. They were on time, the plane was clean, boarding was fairly straightforward and the staff was cheerful and friendly. The only downside was comfort. The seats were fairly hard and after a 2 hour flight your rear end is not feeling so great. Maybe a little more cushion in the seats, Frontier!

Everything you need to know for your flight from Chicago to Clearwater Beach

Complete your trip to Clearwater Beach with a hotel stay or car rental

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.