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Cheap Flights from Chicago to Clearwater

Compare Chicago to Clearwater flight deals

Find the cheapest month or even day of the year to fly to Clearwater

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Flight deals from Chicago to Clearwater

Looking for a cheap last-minute deal or the best return flight from Chicago to Clearwater? Find the lowest prices on one-way and return tickets right here.
Tampa.$186 per passenger.Departing Mon, 11 May, returning Fri, 29 May.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 11 May, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Fri, 29 May, arriving in Chicago Rockford.Price includes taxes and charges.From $186, select.
Tampa.$198 per passenger.Departing Mon, 20 Apr, returning Wed, 29 Apr.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 20 Apr, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Wed, 29 Apr, arriving in Chicago Rockford.Price includes taxes and charges.From $198, select.
Tampa.$249 per passenger.Departing Mon, 11 May, returning Mon, 1 Jun.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 11 May, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Mon, 1 Jun, arriving in Chicago Rockford.Price includes taxes and charges.From $249, select.
Tampa.$255 per passenger.Departing Fri, 14 Aug, returning Mon, 17 Aug.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Fri, 14 Aug, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Mon, 17 Aug, arriving in Chicago Rockford.Price includes taxes and charges.From $255, select.
Tampa.$256 per passenger.Departing Wed, 3 Jun, returning Wed, 17 Jun.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Wed, 3 Jun, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Wed, 17 Jun, arriving in Chicago Rockford.Price includes taxes and charges.From $256, select.
Tampa.$263 per passenger.Departing Mon, 20 Apr, returning Mon, 1 Jun.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 20 Apr, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Mon, 1 Jun, arriving in Chicago Rockford.Price includes taxes and charges.From $263, select.
Tampa.$264 per passenger.Departing Mon, 20 Apr, returning Fri, 8 May.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 20 Apr, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Fri, 8 May, arriving in Chicago Rockford.Price includes taxes and charges.From $264, select.
Tampa.$273 per passenger.Departing Fri, 26 Jun, returning Mon, 13 Jul.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Fri, 26 Jun, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Mon, 13 Jul, arriving in Chicago Rockford.Price includes taxes and charges.From $273, select.
Tampa.$304 per passenger.Departing Wed, 8 Jul, returning Mon, 13 Jul.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Wed, 8 Jul, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Mon, 13 Jul, arriving in Chicago Rockford.Price includes taxes and charges.From $304, select.
Tampa.$320 per passenger.Departing Fri, 24 Jul, returning Mon, 10 Aug.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Fri, 24 Jul, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Mon, 10 Aug, arriving in Chicago Rockford.Price includes taxes and charges.From $320, select.
Tampa.$337 per passenger.Departing Mon, 30 Mar, returning Wed, 8 Apr.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 30 Mar, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Wed, 8 Apr, arriving in Chicago Rockford.Price includes taxes and charges.From $337, select.
Tampa.$367 per passenger.Departing Fri, 16 Oct, returning Mon, 26 Oct.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Fri, 16 Oct, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Mon, 26 Oct, arriving in Chicago Rockford.Price includes taxes and charges.From $367, select.
Tampa.$421 per passenger.Departing Fri, 16 Oct, returning Mon, 2 Nov.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Fri, 16 Oct, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Mon, 2 Nov, arriving in Chicago Rockford.Price includes taxes and charges.From $421, select.
Tampa.$442 per passenger.Departing Mon, 23 Mar, returning Wed, 25 Mar.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 23 Mar, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Wed, 25 Mar, arriving in Chicago Rockford.Price includes taxes and charges.From $442, select.

Chicago to Clearwater: Flight information

The things to know before you go.
Fly intoSt. Pete–Clearwater International Airport
Distance to Clearwater12.7 km
Cheapest flight$186
Cheapest month to flyMay
Most popular airlineAllegiant Air
Average flight time2 hrs, 37 mins

Find the cheapest month to fly from Chicago to Clearwater

We’re always keeping an eye on fares, so you can find the best flight deal in seconds. It looks like Chicago to Clearwater flights are currently cheapest in May. We’ve based this on flights into St. Pete–Clearwater International Airport.
Mar
from $442
Apr
from $198
May
from $186
Jun
from $256
Jul
from $304
Aug
from $255
Sep
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Oct
from $367
Nov
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Dec
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Jan
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Feb
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Finding cheap flights from Chicago to Clearwater: Frequently asked questions

There are 3 airports near Clearwater: St. Pete–Clearwater International Airport, Tampa International Airport and Tampa Peter O'Knight Airport.
The best price we found for a return flight from Chicago to Clearwater is $186. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, Allegiant Air is the only airline that offers direct flights to St. Pete–Clearwater International Airport.
We've checked every Chicago to Clearwater fare we could find, and the cheapest upcoming date to fly seems to be on Monday, 11 May 2026. Overall, the cheapest month to fly from Chicago to Clearwater is usually May.
If you're flying from Chicago, the cheapest airport near Clearwater is St. Pete–Clearwater International – which is 12.7 km away from the centre of Clearwater. We've found flights into this airport from $186.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Clearwater on Monday, 11 May 2026.
No airlines currently offer direct flights between Chicago and Clearwater. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Clearwater but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Clearwater is around 40 days in advance, so don’t leave your flight to the last minute.
St. Pete–Clearwater International Airport is 12.7km from Clearwater, Tampa International Airport is 26.0km from Clearwater, and Tampa Peter O'Knight Airport is 34.9km from Clearwater.
St. Pete–Clearwater International Airport is closest to Clearwater, at around 12.7 km away.
The cheapest airline that flies to Clearwater is Allegiant Air .