$108+ Cheap flights from Chicago (CHI) to Clearwater Beach, FL
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Sep 11 — Sep 181
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Clearwater Beach with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Clearwater Beach are usually found in October or January, booked 89 days in advance, depart on a Wednesday or Saturday and return on a Thursday
Cheap flight deals from Chicago to Clearwater Beach
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Cheapest flights from Chicago to Clearwater BeachExplore the most affordable flight options available from Chicago to Clearwater Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 12, 2026.
Explore the most affordable flight options available from Chicago to Clearwater Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 12, 2026.
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:25 pm -
Nonstop2h 35m
Tue 10/611:20 am -
1 stop4h 00m
Deal found 8/11![Southwest logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:20 am -
1 stop11h 01m
Tue 9/297:26 pm -
2 stops17h 25m
Deal found 8/11![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:59 pm -
2 stops24h 00m
Tue 9/87:05 am -
1 stop14h 03m
Deal found 8/11![Frontier logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2811:15 am -
2 stops10h 19m
Wed 10/77:15 am -
1 stop5h 36m
Deal found 8/11![Frontier logo]()
$206
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:55 pm -
Nonstop2h 35m
Sat 9/126:00 pm -
Nonstop2h 45m
Deal found 8/11![Southwest logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:59 pm -
1 stop9h 36m
Mon 8/312:25 pm -
1 stop18h 28m
Deal found 8/11![Frontier logo]()
$207
This Frontier deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:05 am -
1 stop11h 44m
Wed 9/97:15 am -
1 stop11h 36m
Deal found 8/10![Frontier logo]()
$208
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/34:45 pm -
1 stop5h 43m
Sat 11/77:22 pm -
Nonstop3h 12m
Deal found 8/11![American Airlines logo]()
$208
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:15 pm -
1 stop4h 20m
Mon 11/235:55 pm -
1 stop5h 45m
Deal found 8/12![Southwest logo]()
$209
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:30 pm -
Nonstop2h 56m
Fri 9/111:22 pm -
Nonstop3h 08m
Deal found 8/7![United Airlines logo]()
$209
This Frontier deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:05 am -
1 stop11h 44m
Wed 9/92:10 pm -
1 stop4h 41m
Deal found 8/10![Frontier logo]()
$210
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:59 pm -
Nonstop2h 49m
Sun 9/67:13 pm -
Nonstop3h 17m
Deal found 8/8![American Airlines logo]()
$210
Best flights from Chicago to Clearwater BeachDiscover carefully curated flight deals from Chicago to Clearwater Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 12, 2026.
Discover carefully curated flight deals from Chicago to Clearwater Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 12, 2026.
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:30 am -
1 stop7h 00m
Thu 9/171:22 pm -
Nonstop3h 08m
Deal found 8/11![United Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:55 am -
2 stops6h 15m
Tue 11/34:00 pm -
2 stops6h 25m
Deal found 8/11![Southwest logo]()
$219
This JetBlue deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/23:00 pm -
1 stop5h 14m
Mon 10/58:30 am -
1 stop6h 17m
Deal found 8/9![JetBlue logo]()
$243
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/39:54 am -
1 stop6h 56m
Sun 9/66:20 am -
1 stop7h 20m
Deal found 8/10![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:55 pm -
Nonstop2h 35m
Thu 10/17:50 pm -
Nonstop2h 45m
Deal found 8/7![Southwest logo]()
$235
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/172:10 pm -
1 stop6h 18m
Tue 10/206:00 pm -
Nonstop3h 05m
Deal found 8/7![United Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:45 pm -
1 stop4h 40m
Thu 9/105:15 am -
Nonstop2h 40m
Deal found 8/7![Southwest logo]()
$245
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:55 pm -
Nonstop2h 48m
Sun 10/47:33 pm -
Nonstop3h 05m
Deal found 8/11![United Airlines logo]()
$246
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:55 pm -
Nonstop2h 35m
Thu 9/175:15 am -
Nonstop2h 40m
Deal found 8/11![Southwest logo]()
$245
This KAYAK deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:00 am -
1 stop6h 08m
Thu 9/248:30 am -
1 stop6h 15m
Deal found 8/7![JetBlue logo]()
$308
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:50 am -
1 stop5h 26m
Mon 9/286:00 pm -
Nonstop3h 05m
Deal found 8/11![United Airlines logo]()
$260
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:50 am -
Nonstop2h 30m
Mon 9/145:15 am -
Nonstop2h 40m
Deal found 8/7![Southwest logo]()
$253
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:15 am -
Nonstop2h 56m
Mon 8/317:30 am -
Nonstop3h 03m
Deal found 8/7![United Airlines logo]()
$272
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:45 am -
1 stop6h 25m
Sun 10/46:40 pm -
Nonstop2h 45m
Deal found 8/11![Southwest logo]()
$255
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:45 am -
1 stop5h 43m
Sun 9/612:17 pm -
Nonstop3h 03m
Deal found 8/11![United Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:10 am -
2 stops5h 40m
Mon 9/146:55 am -
1 stop5h 35m
Deal found 8/10![Southwest logo]()
$271
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:15 am -
Nonstop2h 52m
Fri 9/187:05 pm -
1 stop5h 35m
Deal found 8/8![United Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:15 pm -
Nonstop2h 35m
Tue 9/227:35 am -
Nonstop2h 40m
Deal found 8/7![Southwest logo]()
$272
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:59 pm -
Nonstop2h 48m
Sun 10/187:26 am -
Nonstop3h 06m
Deal found 8/11![United Airlines logo]()
$323
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:05 pm -
Nonstop2h 35m
Tue 9/155:35 pm -
Nonstop2h 35m
Deal found 8/9![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3110:55 am -
Nonstop2h 56m
Wed 9/27:30 am -
Nonstop3h 03m
Deal found 8/7![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:50 am -
1 stop5h 35m
Sun 9/137:35 am -
Nonstop2h 40m
Deal found 8/7![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:55 am -
2 stops6h 15m
Mon 10/198:25 pm -
1 stop5h 40m
Deal found 8/10![Southwest logo]()
$304
Last-minute flights from Chicago to Clearwater BeachDiscover last-minute flight deals from Chicago to Clearwater Beach. Data last updated August 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Clearwater Beach. Data last updated August 12, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:59 pm -
1 stop9h 36m
Mon 8/312:25 pm -
1 stop18h 28m
Deal found 8/11![Frontier logo]()
$207
This Super.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:50 am -
1 stop5h 59m
Sat 8/292:25 pm -
1 stop9h 22m
Deal found 8/8![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:50 am -
1 stop11h 45m
Tue 9/12:25 pm -
1 stop9h 22m
Deal found 8/7![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:59 pm -
1 stop9h 36m
Mon 8/318:07 pm -
1 stop12h 46m
Deal found 8/11![Frontier logo]()
$211
This Frontier deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:05 am -
1 stop11h 44m
Wed 9/97:15 am -
1 stop11h 36m
Deal found 8/10![Frontier logo]()
$208
This Frontier deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:05 am -
1 stop11h 44m
Wed 9/92:10 pm -
1 stop4h 41m
Deal found 8/10![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:59 pm -
2 stops24h 00m
Tue 9/87:05 am -
1 stop14h 03m
Deal found 8/11![Frontier logo]()
$205
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:30 pm -
Nonstop2h 56m
Fri 9/111:22 pm -
Nonstop3h 08m
Deal found 8/7![United Airlines logo]()
$209
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:59 pm -
Nonstop2h 49m
Sun 9/67:13 pm -
Nonstop3h 17m
Deal found 8/8![American Airlines logo]()
$210
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:55 pm -
Nonstop2h 35m
Sat 9/126:00 pm -
Nonstop2h 45m
Deal found 8/11![Southwest logo]()
$207
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:42 am -
1 stop6h 56m
Tue 9/227:18 pm -
Nonstop3h 19m
Deal found 8/12![American Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:20 am -
1 stop11h 01m
Tue 9/297:26 pm -
2 stops17h 25m
Deal found 8/11![Frontier logo]()
$204
One-way flights from Chicago to Clearwater BeachSearch for one-way flight options from Chicago to Clearwater Beach. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
Search for one-way flight options from Chicago to Clearwater Beach. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:05 am -
1 stop11h 44m
Deal found 8/10![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:05 am -
1 stop14h 10m
Deal found 8/9![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:14 am -
1 stop6h 30m
Deal found 8/8![Multiple Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2111:50 am -
1 stop22h 50m
Deal found 8/10![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/221:59 pm -
1 stop9h 36m
Deal found 8/10![Frontier logo]()
$110
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:20 pm -
Nonstop2h 40m
Deal found 8/11![Southwest logo]()
$111
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:45 pm -
Nonstop2h 56m
Deal found 8/11![United Airlines logo]()
$111
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:05 pm -
Nonstop2h 35m
Deal found 8/10![Southwest logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:06 pm -
2 stops21h 33m
Deal found 8/11![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:25 am -
1 stop24h 19m
Deal found 8/11![Frontier logo]()
$113
This Cheapflightsfares deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/228:41 pm -
Nonstop2h 59m
Deal found 8/10![Frontier logo]()
$114
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:56 am -
1 stop6h 57m
Deal found 8/10![Delta logo]()
$115
Find flight deals from Chicago to Clearwater Beach
Keep the following information in mind while searching for Chicago to Clearwater Beach flight deals. Data was last updated August 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $204 (Kiwi.com) |
One-way from | $108 (Kiwi.com) |
Popular in | June |
Cheapest in | October |
Average price | $265 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Clearwater Beach that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 12, 2026.
Use the filters below to find and compare flights from Chicago to Clearwater Beach that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoTampa
ORD Chicago O'Hare Intl - TPA Tampa
ORDTPA
Chicago O'Hare Intl
Tue 9/15
7:30 am-3:30 pm
1 stop7h 00m
Tampa
Thu 9/17
1:22 pm-3:30 pm
Nonstop3h 08m
$207
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Fri 10/30
7:55 am-3:10 pm
2 stops6h 15m
Tampa
Tue 11/3
4:00 pm-9:25 pm
2 stops6h 25m
$219
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Mon 9/28
7:55 pm-11:30 pm
Nonstop2h 35m
Tampa
Thu 10/1
7:50 pm-9:35 pm
Nonstop2h 45m
$235
ChicagoTampa
ORD Chicago O'Hare Intl - TPA Tampa
ORDTPA
Chicago O'Hare Intl
Fri 10/2
3:00 pm-9:14 pm
1 stop5h 14m
Tampa
Mon 10/5
8:30 am-1:47 pm
1 stop6h 17m
$243
ChicagoTampa
ORD Chicago O'Hare Intl - TPA Tampa
ORDTPA
Chicago O'Hare Intl
Sat 10/17
2:10 pm-9:28 pm
1 stop6h 18m
Tampa
Tue 10/20
6:00 pm-8:05 pm
Nonstop3h 05m
$245
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Tue 9/8
12:45 pm-6:25 pm
1 stop4h 40m
Tampa
Thu 9/10
5:15 am-6:55 am
Nonstop2h 40m
$245
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Thu 9/10
7:55 pm-11:30 pm
Nonstop2h 35m
Tampa
Thu 9/17
5:15 am-6:55 am
Nonstop2h 40m
$245
ChicagoTampa
ORD Chicago O'Hare Intl - TPA Tampa
ORDTPA
Chicago O'Hare Intl
Thu 10/1
1:55 pm-5:43 pm
Nonstop2h 48m
Tampa
Sun 10/4
7:33 pm-9:38 pm
Nonstop3h 05m
$246
Quickest round-trip
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Sun 9/13
6:50 am-10:20 am
Nonstop2h 30m
Tampa
Mon 9/14
5:15 am-6:55 am
Nonstop2h 40m
$253
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Thu 10/1
6:45 am-2:10 pm
1 stop6h 25m
Tampa
Sun 10/4
6:40 pm-8:25 pm
Nonstop2h 45m
$255
Showing 1-10 of 45 resultsSorted by cheapest first
Best time to book a flight from Chicago to Clearwater Beach
Have a flexible travel schedule? Discover the best time to fly to Clearwater Beach from Chicago with our price prediction graph.
ORD-TPA
MDW-TPA
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Clearwater Beach
CHI-CW9
ORD-TPA
MDW-TPA
What is the cheapest time of day to fly from CHI to CW9?
Find hourly flight availability from Chicago to Clearwater Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 12, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 15% on flights from Chicago to Clearwater Beach by exploring options for tickets in the afternoon.
Weekly flight availability from Chicago to Clearwater Beach
Explore weekly flight availability from Chicago to Clearwater Beach. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 12, 2026.
The most flights from CHI to CW9 are scheduled on a Monday (78 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (17 on average).
How much does it cost to fly round-trip from Chicago to Clearwater Beach?
Airfare is typical for this route at the moment.
Chicago to Clearwater Beach flights typically cost between $203 and $353 in September.The cheapest round-trip price found within the last 5 days was $204 on Frontier (Sep 26-Sep 29).
What is the cheapest day to fly from Chicago to Clearwater Beach?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Clearwater Beach. Price data was last updated on August 8, 2026.
Travelers seeking maximum savings on their Chicago to Clearwater Beach flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Clearwater Beach
Get insights into the airlines that provide service to Clearwater Beach. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Clearwater Beach. Reviews last updated August 12, 2026.
Read through reviews of airlines operating flights from Chicago to Clearwater Beach, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
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Chicago and Clearwater Beach flights
Browse other Chicago and Clearwater Beach flight options. Last updated on August 12, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from Chicago to Clearwater Beach
Discover the top 7 airlines that operate flights from Chicago to Clearwater Beach. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$48 | Average$205 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$221 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$109 | Average$305 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$288 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$372 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$159 | Average$370 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$164 | Average$365 | FlexibilityNo cancel fee | On-time69% |