$103+ 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 8/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jul 29 — Aug 51
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 September, booked 89 days in advance, depart on a Wednesday or Thursday 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 June 29, 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 June 29, 2026.
This Southwest deal was found by Cheapflights users on 6/25. 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 8/177:55 pm
MDW
- TPA
Nonstop2h 30m
Southwest
Thu 8/205:15 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/25![Southwest logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 8/58:05 am
ORD
- TPA
1 stop22h 33m
Multiple Airlines
Wed 8/1210:27 am
TPA
- ORD
1 stop6h 33m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 6/25. 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 7/186:30 am
MDW
- TPA
2 stops6h 50m
Southwest
Sat 7/255:30 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/25![Southwest logo]()
$208
This Cheapflightsfares deal was found by Cheapflights users on 6/25. 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.
Mon 8/1712:44 am
ORD
- TPA
1 stop19h 01m
Frontier
Wed 8/262:25 pm
TPA
- ORD
1 stop6h 43m
Frontier
Deal found 6/25![Frontier logo]()
$208
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.
Tue 8/2512:50 pm
MDW
- TPA
1 stop5h 50m
Southwest
Thu 8/275:15 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/26![Southwest logo]()
$209
This American 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 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
Wed 8/126:23 am
TPA
- ORD
Nonstop3h 07m
American Airlines
Deal found 6/28![American Airlines logo]()
$209
This Frontier deal was found by Cheapflights users on 6/24. 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 8/186:05 am
MDW
- TPA
1 stop11h 44m
Frontier
Wed 8/262:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Deal found 6/24![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 6/24. 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 8/182:06 pm
ORD
- TPA
1 stop9h 29m
Frontier
Tue 8/257:15 am
TPA
- ORD
1 stop9h 45m
Frontier
Deal found 6/24![Frontier logo]()
$210
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.
Thu 8/133:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Mon 8/1711:30 am
TPA
- MDW
1 stop4h 00m
Southwest
Deal found 6/26![Southwest 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 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 6/25. 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 8/218:05 am
ORD
- TPA
1 stop8h 07m
Multiple Airlines
Wed 8/268:57 pm
TPA
- ORD
1 stop16h 53m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 6/25. 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 8/11:18 pm
MDW
- TPA
1 stop6h 51m
Delta
Tue 8/45:15 am
TPA
- MDW
1 stop5h 44m
Delta
Deal found 6/25![Delta logo]()
$213
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 June 29, 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 June 29, 2026.
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 8/296:11 am
MDW
- TPA
1 stop6h 54m
Delta
Sat 9/55:55 pm
TPA
- MDW
1 stop5h 41m
Delta
Deal found 6/28![Delta logo]()
$213
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 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 KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/278:29 pm
ORD
- TPA
Nonstop2h 50m
American Airlines
Thu 7/306:44 am
TPA
- ORD
Nonstop3h 05m
American Airlines
Deal found 6/26![American Airlines logo]()
$429
This Southwest deal was found by Cheapflights users on 6/24. 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 9/1210:10 am
MDW
- TPA
1 stop6h 25m
Southwest
Sat 9/196:20 am
TPA
- MDW
2 stops7h 45m
Southwest
Deal found 6/24![Southwest logo]()
$218
This Delta deal was found by Cheapflights users on 6/24. 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 7/156:35 am
ORD
- TPA
1 stop5h 04m
Delta
Sat 7/186:58 pm
TPA
- ORD
1 stop5h 55m
Delta
Deal found 6/24![Delta logo]()
$213
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 7/256:30 am
MDW
- TPA
2 stops6h 50m
Southwest
Sat 8/16:30 pm
TPA
- MDW
1 stop4h 30m
Southwest
Deal found 6/27![Southwest logo]()
$218
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 8/55:30 am
ORD
- TPA
1 stop4h 59m
Delta
Sat 8/85:15 am
TPA
- ORD
1 stop5h 25m
Delta
Deal found 6/28![Delta logo]()
$213
This Southwest deal was found by Cheapflights users on 6/25. 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 8/133:20 pm
MDW
- TPA
1 stop3h 55m
Southwest
Sat 8/156:20 am
TPA
- MDW
2 stops7h 45m
Southwest
Deal found 6/25![Southwest logo]()
$225
This Delta deal was found by Cheapflights users on 6/25. 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 8/296:40 am
ORD
- TPA
1 stop4h 59m
Delta
Sat 9/512:36 pm
TPA
- ORD
1 stop7h 23m
Delta
Deal found 6/25![Delta logo]()
$213
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:15 am
ORD
- TPA
Nonstop2h 56m
United Airlines
Fri 9/44:23 pm
TPA
- ORD
Nonstop3h 08m
United Airlines
Deal found 6/27![United Airlines logo]()
$289
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.
Tue 7/288:03 am
ORD
- TPA
1 stop5h 10m
Delta
Tue 8/43:10 pm
TPA
- ORD
1 stop6h 45m
Delta
Deal found 6/26![Delta logo]()
$213
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.
Thu 8/135:10 pm
MDW
- TPA
1 stop6h 20m
Delta
Tue 8/184:32 pm
TPA
- MDW
1 stop7h 04m
Delta
Deal found 6/28![Delta logo]()
$219
This United Airlines deal was found by Cheapflights users on 6/25. 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 7/148:40 am
ORD
- TPA
1 stop5h 45m
United Airlines
Sat 7/187:42 pm
TPA
- ORD
Nonstop3h 11m
United Airlines
Deal found 6/25![United Airlines logo]()
$339
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.
Thu 7/305:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Sat 8/19:20 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Deal found 6/27![Southwest logo]()
$283
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 8/151:25 pm
MDW
- TPA
1 stop6h 54m
Delta
Mon 8/176:20 am
TPA
- MDW
1 stop6h 31m
Delta
Deal found 6/28![Delta logo]()
$219
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 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 8/275:10 pm
MDW
- TPA
1 stop6h 20m
Delta
Mon 8/3110:00 am
TPA
- MDW
1 stop6h 44m
Delta
Deal found 6/27![Delta logo]()
$225
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.
Mon 8/106:05 am
MDW
- TPA
1 stop4h 24m
Delta
Sat 8/225:55 pm
TPA
- MDW
1 stop5h 41m
Delta
Deal found 6/26![Delta logo]()
$229
This United Airlines 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 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 6/27![United Airlines logo]()
$425
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.
Sat 7/188:43 am
ORD
- TPA
1 stop5h 23m
United Airlines
Sat 7/257:42 pm
TPA
- ORD
Nonstop3h 11m
United Airlines
Deal found 6/28![United Airlines logo]()
$429
Last-minute flights from Chicago to Clearwater BeachDiscover last-minute flight deals from Chicago to Clearwater Beach. Data last updated June 29, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Clearwater Beach. Data last updated June 29, 2026 and is based on user searches.
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.
Tue 7/148:05 am
ORD
- TPA
1 stop22h 03m
Multiple Airlines
Tue 8/113:09 pm
TPA
- ORD
1 stop22h 06m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 7/145:13 pm
ORD
- TPA
2 stops17h 27m
Multiple Airlines
Tue 7/283:09 pm
TPA
- ORD
1 stop22h 06m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$223
This Trip.com deal was found by Cheapflights users on 6/25. 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.
Wed 7/1512:11 pm
MDW
- TPA
1 stop5h 41m
Frontier
Wed 7/227:00 am
TPA
- MDW
1 stop5h 07m
Frontier
Deal found 6/25![Frontier logo]()
$221
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.
Wed 7/158:05 am
ORD
- TPA
1 stop22h 33m
Multiple Airlines
Tue 8/113:09 pm
TPA
- ORD
1 stop22h 06m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 6/25. 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 7/186:30 am
MDW
- TPA
2 stops6h 50m
Southwest
Sat 7/255:30 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/25![Southwest logo]()
$208
This United Airlines deal was found by Cheapflights users on 6/25. 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 6/25![United Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 7/228:05 am
ORD
- TPA
1 stop22h 33m
Multiple Airlines
Wed 7/292:25 pm
TPA
- ORD
1 stop6h 28m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 6/25. 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 7/256:30 am
MDW
- TPA
2 stops6h 50m
Southwest
Tue 7/287:30 am
TPA
- MDW
1 stop5h 40m
Southwest
Deal found 6/25![Southwest logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 7/257:05 am
ORD
- TPA
1 stop9h 38m
Multiple Airlines
Tue 7/283:09 pm
TPA
- ORD
1 stop22h 06m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$220
This Southwest deal was found by Cheapflights users on 6/25. 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 6/25![Southwest logo]()
$213
This Delta deal was found by Cheapflights users on 6/25. 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 7/287:05 am
ORD
- TPA
1 stop4h 45m
Delta
Tue 8/45:15 am
TPA
- ORD
1 stop5h 08m
Delta
Deal found 6/25![Delta logo]()
$213
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/281:50 pm
ORD
- TPA
1 stop6h 26m
Frontier
Tue 8/42:25 pm
TPA
- ORD
1 stop6h 28m
Frontier
Deal found 6/26![Frontier logo]()
$218
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 June 29, 2026.
Search for one-way flight options from Chicago to Clearwater Beach. Find affordable one-way fares based on user searches. Data last updated June 29, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/24. 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.
Mon 8/312:44 am
ORD
- TPA
1 stop18h 46m
Frontier
Deal found 6/24![Frontier logo]()
$103
This Super.com deal was found by Cheapflights users on 6/24. 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 8/1911:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Deal found 6/24![Frontier logo]()
$103
This American Airlines deal was found by Cheapflights users on 6/24. 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.
Thu 8/65:59 pm
ORD
- TPA
Nonstop2h 49m
American Airlines
Deal found 6/24![American Airlines logo]()
$104
This Super.com deal was found by Cheapflights users on 6/24. 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 6/24![Frontier logo]()
$104
This WAYA deal was found by Cheapflights users on 6/25. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/151:50 pm
ORD
- TPA
1 stop6h 26m
Frontier
Deal found 6/25![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 6/24. 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 8/511:06 am
MDW
- TPA
1 stop6h 29m
Frontier
Deal found 6/24![Frontier logo]()
$105
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.
Fri 9/257:45 am
ORD
- TPA
1 stop7h 16m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$106
This Delta deal was found by Cheapflights users on 6/23. 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 7/285:30 am
ORD
- TPA
1 stop4h 59m
Delta
Deal found 6/23![Delta logo]()
$107
This Southwest deal was found by Cheapflights users on 6/25. 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 7/215:20 pm
MDW
- TPA
1 stop4h 20m
Southwest
Deal found 6/25![Southwest logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 6/24![Multiple Airlines logo]()
$108
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.
Thu 8/2012:20 pm
MDW
- TPA
1 stop3h 50m
Southwest
Deal found 6/26![Southwest logo]()
$108
This United Airlines deal was found by Cheapflights users on 6/25. 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 8/138:45 am
ORD
- TPA
1 stop5h 43m
United Airlines
Deal found 6/25![United Airlines logo]()
$109
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 June 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $207 (Southwest) |
One-way from | $103 (Super.com) |
Popular in | June |
Cheapest in | October |
Average price | $344 |
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 June 29, 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
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
MDW - TPA
MDWTPA
Chicago Midway
Sat 8/29
6:11 am-2:05 pm
1 stop6h 54m
Tampa
Sat 9/5
5:55 pm-10:36 pm
1 stop5h 41m
$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
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Wed 7/15
6:35 am-12:39 pm
1 stop5h 04m
Tampa
Sat 7/18
6:58 pm-11:53 pm
1 stop5h 55m
$213
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Wed 8/5
5:30 am-11:29 am
1 stop4h 59m
Tampa
Sat 8/8
5:15 am-9:40 am
1 stop5h 25m
$213
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Sat 8/29
6:40 am-12:39 pm
1 stop4h 59m
Tampa
Sat 9/5
12:36 pm-6:59 pm
1 stop7h 23m
$213
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Tue 7/28
8:03 am-2:13 pm
1 stop5h 10m
Tampa
Tue 8/4
3:10 pm-8:55 pm
1 stop6h 45m
$213
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 9/12
10:10 am-5:35 pm
1 stop6h 25m
Tampa
Sat 9/19
6:20 am-1:05 pm
2 stops7h 45m
$218
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 7/25
6:30 am-2:20 pm
2 stops6h 50m
Tampa
Sat 8/1
6:30 pm-10:00 pm
1 stop4h 30m
$218
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Thu 8/13
5:10 pm-12:30 am
1 stop6h 20m
Tampa
Tue 8/18
4:32 pm-10:36 pm
1 stop7h 04m
$219
Showing 1-10 of 44 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 June 29, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 16% 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 June 29, 2026.
The most flights from CHI to CW9 are scheduled on a Friday (86 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (55 on average).
How much does it cost to fly round-trip from Chicago to Clearwater Beach?
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 June 27, 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 June 29, 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.
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
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 Beach. 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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Alternative routes for Chicago to Clearwater Beach
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Complete your trip
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Find flights from Chicago to Clearwater Beach, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Clearwater Beach flights
Browse other Chicago and Clearwater Beach flight options. Last updated on June 29, 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 June 29, 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 June 29, 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% |