$105+ Cheap flights from Chicago (CHI) to Clearwater, 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Sep 16 — Sep 231
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Clearwater 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 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
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Cheapest flights from Chicago to ClearwaterExplore the most affordable flight options available from Chicago to Clearwater. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2026.
Explore the most affordable flight options available from Chicago to Clearwater. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2026.
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:00 am -
1 stop6h 08m
Sat 9/191:54 pm -
1 stop6h 47m
Deal found 8/17![Multiple Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 8/13. 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 12/225:20 pm -
1 stop3h 50m
Tue 12/297:20 pm -
1 stop5h 15m
Deal found 8/13![Southwest logo]()
$204
This Frontier deal was found by Cheapflights users on 8/14. 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 12/39:21 pm -
1 stop9h 15m
Thu 12/107:35 am -
Nonstop3h 13m
Deal found 8/14![Frontier logo]()
$204
This Expedia deal was found by Cheapflights users on 8/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:50 am -
1 stop5h 59m
Sat 9/52:25 pm -
1 stop9h 22m
Deal found 8/14![Frontier logo]()
$205
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:00 am -
1 stop11h 53m
Sun 10/48:30 am -
1 stop6h 15m
Deal found 8/17![Multiple Airlines logo]()
$205
This Frontier deal was found by Cheapflights users on 8/14. 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 9/111:50 am -
1 stop5h 59m
Sat 9/52:25 pm -
1 stop9h 22m
Deal found 8/14![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/147:25 am -
1 stop7h 16m
Mon 9/219:22 pm -
2 stops15h 29m
Deal found 8/16![Multiple Airlines logo]()
$206
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 9/107:55 pm -
Nonstop2h 35m
Sat 9/126:00 pm -
Nonstop2h 45m
Deal found 8/12![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Wed 11/42:22 pm -
1 stop6h 17m
Thu 11/59:45 am -
Nonstop3h 05m
Deal found 8/13![United Airlines logo]()
$207
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.
Fri 9/257:55 pm -
Nonstop2h 35m
Mon 9/285:35 pm -
1 stop6h 55m
Deal found 8/12![Southwest logo]()
$208
This Justfly.com 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:00 pm -
1 stop5h 14m
Sat 9/262:03 pm -
1 stop5h 20m
Deal found 8/12![Multiple Airlines logo]()
$208
This Southwest deal was found by Cheapflights users on 8/17. 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 9/126:05 am -
Nonstop2h 30m
Wed 9/167:35 am -
Nonstop2h 40m
Deal found 8/17![Southwest logo]()
$209
Best flights from Chicago to ClearwaterDiscover carefully curated flight deals from Chicago to Clearwater that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 17, 2026.
Discover carefully curated flight deals from Chicago to Clearwater that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 17, 2026.
This United Airlines deal was found by Cheapflights users on 8/16. 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.
Wed 9/94:40 pm -
Nonstop2h 56m
Sat 9/124:23 pm -
Nonstop3h 08m
Deal found 8/16![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 8/16. 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 9/267:05 am -
Nonstop2h 30m
Tue 9/295:35 pm -
Nonstop2h 35m
Deal found 8/16![Southwest logo]()
$209
This JetBlue deal was found by Cheapflights users on 8/15. 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.
Sun 9/276:00 am -
1 stop6h 08m
Fri 10/23:30 pm -
1 stop7h 28m
Deal found 8/15![JetBlue logo]()
$267
This United Airlines deal was found by Cheapflights users on 8/15. 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 10/2412:59 pm -
Nonstop2h 48m
Tue 10/279:17 am -
1 stop6h 34m
Deal found 8/15![United Airlines logo]()
$219
This Southwest deal was found by Cheapflights users on 8/14. 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.
Wed 11/111:20 pm -
Nonstop2h 35m
Mon 11/167:20 am -
Nonstop2h 45m
Deal found 8/14![Southwest logo]()
$222
This United Airlines deal was found by Cheapflights users on 8/16. 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 9/2612:59 pm -
Nonstop2h 48m
Tue 9/298:15 am -
1 stop7h 30m
Deal found 8/16![United Airlines logo]()
$219
This Southwest deal was found by Cheapflights users on 8/16. 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 9/257:55 pm -
Nonstop2h 35m
Mon 9/285:50 pm -
1 stop5h 35m
Deal found 8/16![Southwest logo]()
$232
This United Airlines deal was found by Cheapflights users on 8/14. 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 9/264:45 pm -
Nonstop2h 56m
Sat 10/37:00 am -
1 stop6h 25m
Deal found 8/14![United Airlines logo]()
$219
This Southwest deal was found by Cheapflights users on 8/14. 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 10/96:40 pm -
1 stop4h 35m
Tue 10/137:20 am -
Nonstop2h 40m
Deal found 8/14![Southwest logo]()
$232
This United Airlines deal was found by Cheapflights users on 8/16. 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 10/58:50 am -
1 stop5h 26m
Fri 10/96:00 pm -
Nonstop3h 05m
Deal found 8/16![United Airlines logo]()
$228
This Southwest deal was found by Cheapflights users on 8/16. 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 9/292:05 pm -
1 stop6h 25m
Fri 10/25:10 pm -
Nonstop2h 45m
Deal found 8/16![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 8/13. 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 9/62:55 pm -
1 stop5h 20m
Sat 9/126:00 pm -
Nonstop2h 45m
Deal found 8/13![Southwest logo]()
$235
This United Airlines deal was found by Cheapflights users on 8/16. 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 10/34:45 pm -
Nonstop2h 56m
Sun 10/47:26 am -
Nonstop3h 06m
Deal found 8/16![United Airlines logo]()
$240
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.
Sun 9/136:50 am -
Nonstop2h 30m
Sat 9/198:15 am -
2 stops7h 05m
Deal found 8/12![Southwest logo]()
$238
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:59 pm -
Nonstop2h 48m
Mon 10/261:54 pm -
Nonstop3h 03m
Deal found 8/12![United Airlines logo]()
$245
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.
Sat 9/266:35 am -
1 stop7h 30m
Sat 10/311:55 am -
2 stops7h 50m
Deal found 8/12![Southwest logo]()
$247
This United Airlines deal was found by Cheapflights users on 8/14. 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 9/58:45 am -
1 stop5h 13m
Mon 9/77:30 am -
Nonstop3h 03m
Deal found 8/14![United Airlines logo]()
$262
This Southwest deal was found by Cheapflights users on 8/16. 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.
Wed 9/307:40 am -
2 stops6h 10m
Wed 10/72:35 pm -
2 stops6h 15m
Deal found 8/16![Southwest logo]()
$252
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/284:45 pm -
Nonstop2h 56m
Wed 9/307:33 pm -
Nonstop3h 05m
Deal found 8/12![United Airlines logo]()
$278
This Southwest deal was found by Cheapflights users on 8/15. 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 9/57:05 am -
Nonstop2h 30m
Mon 9/145:15 am -
Nonstop2h 40m
Deal found 8/15![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 8/16. 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 10/129:00 pm -
Nonstop2h 30m
Fri 10/166:55 pm -
1 stop5h 15m
Deal found 8/16![Southwest logo]()
$263
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:15 am -
Nonstop2h 56m
Mon 9/77:30 am -
Nonstop3h 03m
Deal found 8/12![United Airlines logo]()
$290
This United Airlines deal was found by Cheapflights users on 8/16. 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 9/48:45 am -
1 stop5h 43m
Fri 9/111:22 pm -
Nonstop3h 08m
Deal found 8/16![United Airlines logo]()
$339
Last-minute flights from Chicago to ClearwaterDiscover last-minute flight deals from Chicago to Clearwater. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Clearwater. Data last updated August 17, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/14. 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 9/111:50 am -
1 stop5h 59m
Sat 9/52:25 pm -
1 stop9h 22m
Deal found 8/14![Frontier logo]()
$206
This Expedia deal was found by Cheapflights users on 8/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:50 am -
1 stop5h 59m
Sat 9/52:25 pm -
1 stop9h 22m
Deal found 8/14![Frontier logo]()
$205
This Cheapflightsfares deal was found by Cheapflights users on 8/14. 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.
Fri 9/42:25 pm -
1 stop22h 34m
Sat 9/128:01 pm -
1 stop29h 22m
Deal found 8/14![Frontier logo]()
$204
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 9/107:55 pm -
Nonstop2h 35m
Sat 9/126:00 pm -
Nonstop2h 45m
Deal found 8/12![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 8/17. 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 9/126:05 am -
Nonstop2h 30m
Wed 9/167:35 am -
Nonstop2h 40m
Deal found 8/17![Southwest logo]()
$209
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:00 am -
1 stop6h 08m
Sat 9/191:54 pm -
1 stop6h 47m
Deal found 8/17![Multiple Airlines logo]()
$199
This Expedia deal was found by Cheapflights users on 8/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:00 am -
1 stop6h 08m
Mon 9/148:01 pm -
1 stop29h 22m
Deal found 8/14![Multiple Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/147:25 am -
1 stop7h 16m
Mon 9/219:22 pm -
2 stops15h 29m
Deal found 8/17![Multiple Airlines logo]()
$207
This Justfly.com 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:00 pm -
1 stop5h 14m
Sat 9/262:03 pm -
1 stop5h 20m
Deal found 8/12![Multiple Airlines logo]()
$208
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/197:00 pm -
Nonstop2h 52m
Sat 9/267:18 pm -
Nonstop3h 19m
Deal found 8/14![American Airlines logo]()
$209
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.
Fri 9/257:55 pm -
Nonstop2h 35m
Mon 9/285:35 pm -
1 stop6h 55m
Deal found 8/12![Southwest logo]()
$208
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/292:40 pm -
Nonstop2h 48m
Tue 10/66:50 am -
Nonstop3h 06m
Deal found 8/14![American Airlines logo]()
$210
One-way flights from Chicago to ClearwaterSearch for one-way flight options from Chicago to Clearwater. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
Search for one-way flight options from Chicago to Clearwater. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
This Southwest deal was found by Cheapflights users on 8/14. 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 10/195:05 am -
Nonstop2h 30m
Deal found 8/14![Southwest logo]()
$105
This United Airlines deal was found by Cheapflights users on 8/17. 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 8/17![United Airlines logo]()
$105
This Trip.com deal was found by Cheapflights users on 8/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:50 am -
1 stop5h 59m
Deal found 8/15![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 10/156:00 am -
2 stops15h 34m
Deal found 8/14![Frontier logo]()
$106
This Booking.com deal was found by Cheapflights users on 8/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:37 am -
1 stop11h 55m
Deal found 8/13![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Tue 9/88:05 am -
2 stops26h 34m
Deal found 8/16![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 10/141:12 pm -
2 stops27h 02m
Deal found 8/14![Frontier logo]()
$109
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:25 am -
2 stops14h 09m
Deal found 8/12![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Tue 9/17:44 pm -
2 stops14h 56m
Deal found 8/13![Frontier logo]()
$110
This Southwest deal was found by Cheapflights users on 8/13. 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 9/47:55 pm -
Nonstop2h 35m
Deal found 8/13![Southwest logo]()
$111
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.
Fri 9/45:59 pm -
Nonstop2h 49m
Deal found 8/12![American Airlines logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/166:25 am -
2 stops12h 21m
Deal found 8/14![Frontier logo]()
$113
Find flight deals from Chicago to Clearwater
Keep the following information in mind while searching for Chicago to Clearwater flight deals. Data was last updated August 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $199 (CheapOair) |
One-way from | $105 (Southwest) |
Popular in | June |
Cheapest in | October |
Average price | $290 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Clearwater 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 17, 2026.
Use the filters below to find and compare flights from Chicago to Clearwater 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
Wed 9/9
4:40 pm-8:36 pm
Nonstop2h 56m
Tampa
Sat 9/12
4:23 pm-6:31 pm
Nonstop3h 08m
$209
Quickest round-trip
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Sat 9/26
7:05 am-10:35 am
Nonstop2h 30m
Tampa
Tue 9/29
5:35 pm-7:10 pm
Nonstop2h 35m
$209
ChicagoTampa
ORD Chicago O'Hare Intl - TPA Tampa
ORDTPA
Chicago O'Hare Intl
Sat 10/24
12:59 pm-4:47 pm
Nonstop2h 48m
Tampa
Tue 10/27
9:17 am-2:51 pm
1 stop6h 34m
$219
ChicagoTampa
ORD Chicago O'Hare Intl - TPA Tampa
ORDTPA
Chicago O'Hare Intl
Sat 9/26
12:59 pm-4:47 pm
Nonstop2h 48m
Tampa
Tue 9/29
8:15 am-2:45 pm
1 stop7h 30m
$219
ChicagoTampa
ORD Chicago O'Hare Intl - TPA Tampa
ORDTPA
Chicago O'Hare Intl
Sat 9/26
4:45 pm-8:41 pm
Nonstop2h 56m
Tampa
Sat 10/3
7:00 am-12:25 pm
1 stop6h 25m
$219
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Wed 11/11
1:20 pm-4:55 pm
Nonstop2h 35m
Tampa
Mon 11/16
7:20 am-9:05 am
Nonstop2h 45m
$222
ChicagoTampa
ORD Chicago O'Hare Intl - TPA Tampa
ORDTPA
Chicago O'Hare Intl
Mon 10/5
8:50 am-3:16 pm
1 stop5h 26m
Tampa
Fri 10/9
6:00 pm-8:05 pm
Nonstop3h 05m
$228
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Fri 9/25
7:55 pm-11:30 pm
Nonstop2h 35m
Tampa
Mon 9/28
5:50 pm-10:25 pm
1 stop5h 35m
$232
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Fri 10/9
6:40 pm-12:15 am
1 stop4h 35m
Tampa
Tue 10/13
7:20 am-9:00 am
Nonstop2h 40m
$232
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Tue 9/29
2:05 pm-9:30 pm
1 stop6h 25m
Tampa
Fri 10/2
5:10 pm-6:55 pm
Nonstop2h 45m
$232
Showing 1-10 of 45 resultsSorted by cheapest first
Best time to book a flight from Chicago to Clearwater
Have a flexible travel schedule? Discover the best time to fly to Clearwater 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
CHI-CL9
ORD-TPA
MDW-TPA
What is the cheapest time of day to fly from CHI to CL9?
Find hourly flight availability from Chicago to Clearwater. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 17, 2026.
It’s typically best to fly out from Chicago to Clearwater in the afternoon. Doing so could potentially save you 15% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Chicago to Clearwater
Explore weekly flight availability from Chicago to Clearwater. 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 17, 2026.
The most flights from CHI to CL9 are scheduled on a Sunday (77 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (50 on average).
How much does it cost to fly round-trip from Chicago to Clearwater?
Airfare is below average for this route at the moment.
Chicago to Clearwater flights typically cost between $209 and $391 in September.The cheapest round-trip price found within the last 5 days was $199 on Multiple Airlines (Sep 13-Sep 19).
What is the cheapest day to fly from Chicago to Clearwater?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Clearwater. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their Chicago to Clearwater 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
Get insights into the airlines that provide service to Clearwater. 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. Reviews last updated August 17, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Clearwater to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Clearwater. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Search flights from Chicago to Clearwater by cabin class
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Chicago and Clearwater flights
Browse other Chicago and Clearwater flight options. Last updated on August 17, 2026.
Other flights from Chicago
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Popular flight searches
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Chicago to Clearwater flights
Consider these flights traveling from Chicago to Clearwater.
Top 7 airlines flying from Chicago to Clearwater
Discover the top 7 airlines that operate flights from Chicago to Clearwater. 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 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$48 | Average$215 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$221 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$109 | Average$322 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$288 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$159 | Average$371 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$162 | Average$373 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$165 | Average$366 | FlexibilityNo cancel fee | On-time69% |