$104+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jul 31 — Aug 71
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 September, booked 89 days in advance, depart on a Wednesday or Thursday and return on a Thursday
Cheap flight deals from Chicago to Clearwater
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Best
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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 July 1, 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 July 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 7/288:05 am
ORD
- TPA
1 stop22h 03m
Multiple Airlines
Wed 8/52:10 pm
TPA
- ORD
1 stop6h 43m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 10/17:45 am
ORD
- TPA
1 stop7h 01m
Multiple Airlines
Mon 10/57:00 am
TPA
- ORD
1 stop6h 02m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Wed 8/51:50 pm
ORD
- TPA
1 stop6h 55m
Frontier
Wed 8/1210:27 am
TPA
- ORD
1 stop6h 33m
Frontier
Deal found 6/30![Frontier logo]()
$208
This Southwest deal was found by Cheapflights users on 6/30. 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 8/117:40 am
MDW
- TPA
2 stops6h 10m
Southwest
Tue 8/187:35 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/30![Southwest logo]()
$208
This American Airlines deal was found by Cheapflights users on 6/30. 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 8/85:59 pm
ORD
- TPA
Nonstop2h 49m
American Airlines
Mon 8/107:13 pm
TPA
- ORD
Nonstop3h 17m
American Airlines
Deal found 6/30![American Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 6/29. 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 8/67:55 pm
MDW
- TPA
Nonstop2h 30m
Southwest
Wed 8/127:35 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/29![Southwest logo]()
$209
This Frontier deal was found by Cheapflights users on 6/30. 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 8/187:10 am
ORD
- TPA
1 stop10h 39m
Frontier
Wed 8/267:15 am
TPA
- ORD
1 stop9h 45m
Frontier
Deal found 6/30![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 6/28. 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 8/1811:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Wed 8/262:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Deal found 6/28![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 9/38:05 am
ORD
- TPA
1 stop6h 39m
Multiple Airlines
Fri 9/48:07 pm
TPA
- ORD
1 stop12h 46m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 10/112:03 pm
MDW
- TPA
1 stop9h 54m
Frontier
Mon 10/57:00 am
TPA
- MDW
1 stop4h 58m
Frontier
Deal found 6/27![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 9/122:03 pm
ORD
- TPA
1 stop7h 54m
Frontier
Tue 9/157:00 am
TPA
- ORD
1 stop6h 02m
Frontier
Deal found 7/1![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 9/127:25 am
MDW
- TPA
1 stop8h 53m
Frontier
Tue 9/157:00 am
TPA
- MDW
1 stop4h 58m
Frontier
Deal found 7/1![Frontier logo]()
$212
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 July 1, 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 July 1, 2026.
This Southwest deal was found by Cheapflights users on 7/1. 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 8/116:00 am
MDW
- TPA
2 stops7h 05m
Southwest
Wed 9/25:35 pm
TPA
- MDW
Nonstop2h 35m
Southwest
Deal found 7/1![Southwest logo]()
$208
This Delta deal was found by Cheapflights users on 6/26. 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 8/17:00 am
ORD
- TPA
1 stop4h 39m
Delta
Tue 8/41:44 pm
TPA
- ORD
1 stop6h 05m
Delta
Deal found 6/26![Delta logo]()
$213
This United Airlines deal was found by Cheapflights users on 6/30. 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 8/137:15 am
ORD
- TPA
Nonstop2h 56m
United Airlines
Mon 8/175:23 pm
TPA
- ORD
1 stop7h 03m
United Airlines
Deal found 6/30![United Airlines logo]()
$235
This Southwest deal was found by Cheapflights users on 6/26. 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 8/56:00 am
MDW
- TPA
2 stops7h 05m
Southwest
Wed 8/127:35 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/26![Southwest logo]()
$208
This Delta deal was found by Cheapflights users on 6/28. 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 8/88:05 am
ORD
- TPA
1 stop6h 22m
Delta
Wed 8/1210:00 am
TPA
- ORD
1 stop5h 09m
Delta
Deal found 6/28![Delta logo]()
$213
This United Airlines deal was found by Cheapflights users on 6/29. 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 8/611:19 am
ORD
- TPA
Nonstop2h 53m
United Airlines
Wed 8/127:30 am
TPA
- ORD
Nonstop3h 03m
United Airlines
Deal found 6/29![United Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 6/27. 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 8/131:25 pm
MDW
- TPA
1 stop6h 54m
Delta
Tue 8/186:20 am
TPA
- MDW
1 stop4h 39m
Delta
Deal found 6/27![Delta logo]()
$219
This Delta deal was found by Cheapflights users on 6/28. 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.
Wed 8/1912:46 pm
MDW
- TPA
1 stop6h 25m
Delta
Mon 8/246:20 am
TPA
- MDW
1 stop4h 39m
Delta
Deal found 6/28![Delta logo]()
$219
This United Airlines deal was found by Cheapflights users on 6/28. 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 8/258:45 am
ORD
- TPA
1 stop5h 43m
United Airlines
Thu 9/37:30 am
TPA
- ORD
Nonstop3h 03m
United Airlines
Deal found 6/28![United Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 6/30. 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 7/218:15 pm
MDW
- TPA
Nonstop2h 40m
Southwest
Tue 8/47:35 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/30![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 6/27. 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.
Wed 8/1910:33 am
ORD
- TPA
1 stop5h 15m
Delta
Mon 8/245:55 pm
TPA
- ORD
1 stop7h 02m
Delta
Deal found 6/27![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 6/27. 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.
Mon 8/106:05 am
MDW
- TPA
1 stop5h 24m
Delta
Sat 8/225:55 pm
TPA
- MDW
1 stop5h 41m
Delta
Deal found 6/27![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 6/26. 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 7/265:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Sat 8/19:20 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Deal found 6/26![Southwest logo]()
$283
This United Airlines deal was found by Cheapflights users on 7/1. 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 8/174:30 pm
ORD
- TPA
Nonstop2h 56m
United Airlines
Fri 8/215:23 pm
TPA
- ORD
1 stop7h 03m
United Airlines
Deal found 7/1![United Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 6/27. 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 8/256:05 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Fri 8/2811:30 am
TPA
- MDW
1 stop4h 00m
Southwest
Deal found 6/27![Southwest logo]()
$289
This United Airlines deal was found by Cheapflights users on 6/30. 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 7/147:31 am
ORD
- TPA
Nonstop2h 53m
United Airlines
Wed 7/297:42 pm
TPA
- ORD
Nonstop3h 11m
United Airlines
Deal found 6/30![United Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 6/30. 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 9/36:20 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Mon 9/711:30 am
TPA
- MDW
1 stop4h 00m
Southwest
Deal found 6/30![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 6/27. 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 7/1812:55 pm
MDW
- TPA
1 stop4h 50m
Southwest
Sat 7/255:30 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/27![Southwest logo]()
$309
This United Airlines deal was found by Cheapflights users on 7/1. 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 7/197:29 am
ORD
- TPA
Nonstop2h 53m
United Airlines
Wed 8/54:30 pm
TPA
- ORD
Nonstop3h 10m
United Airlines
Deal found 7/1![United Airlines logo]()
$358
This United Airlines deal was found by Cheapflights users on 6/30. 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 7/218:40 am
ORD
- TPA
1 stop5h 45m
United Airlines
Fri 7/247:42 pm
TPA
- ORD
Nonstop3h 11m
United Airlines
Deal found 6/30![United Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 7/1. 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 8/298:45 am
ORD
- TPA
1 stop5h 13m
United Airlines
Sat 9/54:04 pm
TPA
- ORD
2 stops8h 36m
United Airlines
Deal found 7/1![United Airlines logo]()
$425
Last-minute flights from Chicago to ClearwaterDiscover last-minute flight deals from Chicago to Clearwater. Data last updated July 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Clearwater. Data last updated July 1, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/29. 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 7/218:40 am
ORD
- TPA
1 stop5h 45m
United Airlines
Tue 7/286:57 pm
TPA
- ORD
1 stop5h 34m
United Airlines
Deal found 6/29![United Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 7/211:50 pm
ORD
- TPA
1 stop6h 26m
Multiple Airlines
Mon 7/2710:31 pm
TPA
- ORD
1 stop14h 44m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 7/288:05 am
ORD
- TPA
1 stop22h 03m
Multiple Airlines
Wed 8/52:10 pm
TPA
- ORD
1 stop6h 43m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$206
This Southwest deal was found by Cheapflights users on 6/30. 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 7/285:10 pm
MDW
- TPA
1 stop4h 25m
Southwest
Tue 8/42:45 pm
TPA
- MDW
1 stop6h 45m
Southwest
Deal found 6/30![Southwest logo]()
$213
This Delta deal was found by Cheapflights users on 7/1. 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.
Tue 7/288:03 am
ORD
- TPA
1 stop5h 10m
Delta
Tue 8/43:10 pm
TPA
- ORD
1 stop6h 45m
Delta
Deal found 7/1![Delta logo]()
$213
This Cheapflightsfares deal was found by Cheapflights users on 6/29. 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 7/289:34 pm
ORD
- TPA
1 stop10h 35m
Frontier
Tue 8/410:27 am
TPA
- ORD
1 stop10h 48m
Frontier
Deal found 6/29![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 7/298:05 am
ORD
- TPA
1 stop22h 33m
Multiple Airlines
Wed 8/510:27 am
TPA
- ORD
1 stop6h 33m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 6/29. 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 8/67:55 pm
MDW
- TPA
Nonstop2h 30m
Southwest
Wed 8/127:35 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/29![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 6/30. 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 8/117:40 am
MDW
- TPA
2 stops6h 10m
Southwest
Tue 8/187:35 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/30![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 6/29. 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 8/1310:05 am
MDW
- TPA
1 stop6h 50m
Southwest
Thu 8/205:15 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/29![Southwest logo]()
$215
This Frontier deal was found by Cheapflights users on 6/28. 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 8/1811:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Wed 8/262:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Deal found 6/28![Frontier logo]()
$210
This Southwest deal was found by Cheapflights users on 6/28. 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 8/256:00 am
MDW
- TPA
2 stops7h 05m
Southwest
Thu 9/35:15 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/28![Southwest logo]()
$214
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 July 1, 2026.
Search for one-way flight options from Chicago to Clearwater. Find affordable one-way fares based on user searches. Data last updated July 1, 2026.
This Super.com deal was found by Cheapflights users on 6/30. 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.
Tue 8/412:11 pm
MDW
- TPA
1 stop5h 41m
Frontier
Deal found 6/30![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 8/68:05 am
ORD
- TPA
1 stop22h 18m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$104
This Frontier deal was found by Cheapflights users on 6/30. 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.
Wed 9/211:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Deal found 6/30![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 6/29. 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 8/41:50 pm
ORD
- TPA
1 stop6h 26m
Frontier
Deal found 6/29![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 9/196:30 am
ORD
- TPA
1 stop9h 48m
Frontier
Deal found 6/30![Frontier logo]()
$106
This Southwest deal was found by Cheapflights users on 6/30. 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 7/281:00 pm
MDW
- TPA
1 stop5h 55m
Southwest
Deal found 6/30![Southwest logo]()
$107
This Delta deal was found by Cheapflights users on 6/30. 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.
Tue 7/286:35 am
ORD
- TPA
1 stop5h 04m
Delta
Deal found 6/30![Delta logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 8/208:05 am
ORD
- TPA
1 stop6h 39m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 8/308:05 am
ORD
- TPA
1 stop22h 18m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 9/277:45 am
ORD
- TPA
1 stop22h 20m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$110
This Southwest deal was found by Cheapflights users on 6/30. 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 8/16:30 am
MDW
- TPA
2 stops6h 50m
Southwest
Deal found 6/30![Southwest logo]()
$112
This Southwest deal was found by Cheapflights users on 6/30. 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 8/106:20 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 6/30![Southwest 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 July 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $206 (Kiwi.com) |
One-way from | $104 (Super.com) |
Popular in | June |
Cheapest in | October |
Average price | $283 |
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 July 1, 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
MDW - TPA
MDWTPA
Chicago Midway
Tue 8/11
6:00 am-2:05 pm
2 stops7h 05m
Tampa
Wed 9/2
5:35 pm-7:10 pm
Nonstop2h 35m
$208
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Wed 8/5
6:00 am-2:05 pm
2 stops7h 05m
Tampa
Wed 8/12
7:35 am-9:15 am
Nonstop2h 40m
$208
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Sat 8/1
7:00 am-12:39 pm
1 stop4h 39m
Tampa
Tue 8/4
1:44 pm-6:49 pm
1 stop6h 05m
$213
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Sat 8/8
8:05 am-3:27 pm
1 stop6h 22m
Tampa
Wed 8/12
10:00 am-2:09 pm
1 stop5h 09m
$213
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Thu 8/13
1:25 pm-9:19 pm
1 stop6h 54m
Tampa
Tue 8/18
6:20 am-9:59 am
1 stop4h 39m
$219
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Wed 8/19
12:46 pm-8:11 pm
1 stop6h 25m
Tampa
Mon 8/24
6:20 am-9:59 am
1 stop4h 39m
$219
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Wed 8/19
10:33 am-4:48 pm
1 stop5h 15m
Tampa
Mon 8/24
5:55 pm-11:57 pm
1 stop7h 02m
$229
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Mon 8/10
6:05 am-12:29 pm
1 stop5h 24m
Tampa
Sat 8/22
5:55 pm-10:36 pm
1 stop5h 41m
$229
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Thu 8/13
7:15 am-11:11 am
Nonstop2h 56m
Tampa
Mon 8/17
5:23 pm-11:26 pm
1 stop7h 03m
$235
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Thu 8/6
11:19 am-3:12 pm
Nonstop2h 53m
Tampa
Wed 8/12
7:30 am-9:33 am
Nonstop3h 03m
$239
Showing 1-10 of 41 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 July 1, 2026.
It’s typically best to fly out from Chicago to Clearwater in the afternoon. Doing so could potentially save you 16% 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 July 1, 2026.
The most flights from CHI to CL9 are scheduled on a Wednesday (77 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (36 on average).
How much does it cost to fly round-trip from Chicago to Clearwater?
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 June 27, 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 July 1, 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.
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
7.9
Food
7.0
Entertainment
7.5
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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chicago to Clearwater
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Complete your trip
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Search flights from Chicago to Clearwater by cabin class
Find flights from Chicago to Clearwater, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Clearwater flights
Browse other Chicago and Clearwater flight options. Last updated on July 1, 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 July 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 July 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$48 | Average$209 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$109 | Average$304 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$113 | Average$215 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$147 | Average$288 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$365 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$156 | Average$369 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$158 | Average$363 | FlexibilityNo cancel fee | On-time69% |