$84+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jun 9 — Jun 161
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 September or October, booked 30 days in advance, depart on a Wednesday or Saturday and return on a Friday
Cheap flight deals from Chicago to Clearwater Beach
Cheapest
Best
Last-minute
One-way
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 May 10, 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 May 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 6/301:29 pm
ORD
- TPA
1 stop6h 48m
Frontier
Tue 7/72:25 pm
TPA
- ORD
1 stop6h 28m
Frontier
Deal found 5/6![Frontier logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 8/512:11 pm
MDW
- TPA
1 stop5h 41m
Frontier
Wed 8/124:46 pm
TPA
- MDW
1 stop6h 22m
Frontier
Deal found 5/6![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:27 pm
MDW
- TPA
1 stop5h 24m
Frontier
Tue 6/164:46 pm
TPA
- MDW
1 stop6h 25m
Frontier
Deal found 5/9![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:55 am
ORD
- TPA
1 stop10h 56m
Frontier
Tue 6/162:25 pm
TPA
- ORD
1 stop6h 25m
Frontier
Deal found 5/9![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
MDW
- TPA
1 stop14h 17m
Frontier
Fri 7/32:25 pm
TPA
- MDW
1 stop8h 46m
Frontier
Deal found 5/7![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/281:50 pm
ORD
- TPA
1 stop20h 49m
Frontier
Wed 6/32:25 pm
TPA
- ORD
1 stop6h 04m
Frontier
Deal found 5/9![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:04 pm
MDW
- TPA
1 stop5h 47m
Frontier
Wed 6/32:25 pm
TPA
- MDW
1 stop8h 37m
Frontier
Deal found 5/10![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:55 am
ORD
- TPA
1 stop10h 56m
Frontier
Tue 6/24:46 pm
TPA
- ORD
1 stop16h 09m
Frontier
Deal found 5/9![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/912:27 pm
MDW
- TPA
1 stop5h 24m
Frontier
Wed 6/177:45 am
TPA
- MDW
2 stops15h 26m
Frontier
Deal found 5/5![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 6/36:55 am
ORD
- TPA
1 stop10h 56m
Frontier
Tue 6/97:45 am
TPA
- ORD
2 stops13h 08m
Frontier
Deal found 5/6![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 6/312:04 pm
MDW
- TPA
1 stop8h 23m
Frontier
Tue 6/97:45 am
TPA
- MDW
2 stops15h 26m
Frontier
Deal found 5/6![Frontier logo]()
$165
This Southwest deal was found by Cheapflights users on 5/6. 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 6/305:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Tue 7/79:55 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/6![Southwest logo]()
$169
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 May 10, 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 May 10, 2026.
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Wed 9/92:45 pm
TPA
- MDW
1 stop5h 20m
Southwest
Deal found 5/8![Southwest logo]()
$179
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:15 pm
ORD
- TPA
1 stop5h 49m
Delta
Wed 9/307:59 pm
TPA
- ORD
1 stop4h 58m
Delta
Deal found 5/10![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:40 am
ORD
- TPA
1 stop5h 45m
United Airlines
Tue 7/77:42 pm
TPA
- ORD
Nonstop3h 11m
United Airlines
Deal found 5/9![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 5/6. 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 8/57:40 am
MDW
- TPA
2 stops6h 10m
Southwest
Wed 8/127:00 pm
TPA
- MDW
1 stop4h 20m
Southwest
Deal found 5/6![Southwest logo]()
$194
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/99:48 am
ORD
- TPA
1 stop4h 39m
Delta
Tue 6/167:57 pm
TPA
- ORD
1 stop5h 02m
Delta
Deal found 5/9![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/294:20 pm
ORD
- TPA
Nonstop2h 56m
United Airlines
Sat 9/57:30 am
TPA
- ORD
Nonstop3h 03m
United Airlines
Deal found 5/10![United Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Wed 6/249:55 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/8![Southwest logo]()
$205
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/211:26 am
ORD
- TPA
1 stop5h 15m
Delta
Mon 6/87:57 pm
TPA
- ORD
1 stop5h 02m
Delta
Deal found 5/10![Delta logo]()
$208
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:00 am
ORD
- TPA
Nonstop2h 56m
United Airlines
Wed 9/95:32 pm
TPA
- ORD
1 stop6h 45m
United Airlines
Deal found 5/8![United Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 5/6. 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 5/2811:26 am
ORD
- TPA
1 stop6h 25m
Delta
Tue 6/25:46 pm
TPA
- ORD
1 stop5h 41m
Delta
Deal found 5/6![Delta logo]()
$208
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Wed 9/232:45 pm
TPA
- MDW
1 stop5h 20m
Southwest
Deal found 5/8![Southwest logo]()
$215
This United Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:30 pm
ORD
- TPA
Nonstop2h 54m
United Airlines
Sat 6/67:05 am
TPA
- ORD
1 stop7h 03m
United Airlines
Deal found 5/9![United Airlines logo]()
$219
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:30 am
MDW
- TPA
2 stops6h 20m
Southwest
Sat 10/313:10 pm
TPA
- MDW
1 stop4h 00m
Southwest
Deal found 5/6![Southwest logo]()
$220
This Delta deal was found by Cheapflights users on 5/6. 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.
Fri 7/33:22 pm
ORD
- TPA
1 stop5h 08m
Delta
Tue 7/75:53 pm
TPA
- ORD
1 stop7h 00m
Delta
Deal found 5/6![Delta logo]()
$243
This United Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/205:59 pm
ORD
- TPA
Nonstop2h 53m
United Airlines
Tue 6/236:57 pm
TPA
- ORD
1 stop5h 29m
United Airlines
Deal found 5/10![United Airlines logo]()
$251
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/195:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Tue 6/239:55 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/8![Southwest logo]()
$230
This United Airlines deal was found by Cheapflights users on 5/6. 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 5/272:26 pm
ORD
- TPA
Nonstop2h 54m
United Airlines
Sun 5/317:35 am
TPA
- ORD
Nonstop3h 10m
United Airlines
Deal found 5/6![United Airlines logo]()
$259
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/185:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Tue 6/234:40 pm
TPA
- MDW
1 stop4h 15m
Southwest
Deal found 5/8![Southwest logo]()
$240
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/235:30 am
ORD
- TPA
1 stop5h 04m
Delta
Sun 6/287:57 pm
TPA
- ORD
1 stop5h 02m
Delta
Deal found 5/10![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 5/6. 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 6/303:10 pm
MDW
- TPA
2 stops7h 00m
Southwest
Tue 7/77:45 pm
TPA
- MDW
1 stop4h 25m
Southwest
Deal found 5/6![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 5/6. 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 5/2912:45 pm
MDW
- TPA
2 stops6h 30m
Southwest
Mon 6/13:55 pm
TPA
- MDW
1 stop5h 40m
Southwest
Deal found 5/6![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 5/5. 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 6/54:40 pm
MDW
- TPA
1 stop4h 15m
Southwest
Mon 6/810:30 pm
TPA
- MDW
Nonstop2h 35m
Southwest
Deal found 5/5![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/268:10 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Sat 6/275:30 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/7![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/195:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Mon 6/225:20 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/7![Southwest logo]()
$291
Last-minute flights from Chicago to Clearwater BeachDiscover last-minute flight deals from Chicago to Clearwater Beach. Data last updated May 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Clearwater Beach. Data last updated May 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:55 am
ORD
- TPA
1 stop10h 56m
Frontier
Tue 6/24:46 pm
TPA
- ORD
1 stop16h 09m
Frontier
Deal found 5/9![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:04 pm
MDW
- TPA
1 stop5h 47m
Frontier
Wed 6/32:25 pm
TPA
- MDW
1 stop8h 37m
Frontier
Deal found 5/10![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/281:50 pm
ORD
- TPA
1 stop20h 49m
Frontier
Wed 6/32:25 pm
TPA
- ORD
1 stop6h 04m
Frontier
Deal found 5/9![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 6/36:55 am
ORD
- TPA
1 stop10h 56m
Frontier
Tue 6/97:45 am
TPA
- ORD
2 stops13h 08m
Frontier
Deal found 5/6![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 6/312:04 pm
MDW
- TPA
1 stop8h 23m
Frontier
Tue 6/97:45 am
TPA
- MDW
2 stops15h 26m
Frontier
Deal found 5/6![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:55 am
ORD
- TPA
1 stop10h 56m
Frontier
Tue 6/162:25 pm
TPA
- ORD
1 stop6h 25m
Frontier
Deal found 5/9![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:27 pm
MDW
- TPA
1 stop5h 24m
Frontier
Tue 6/164:46 pm
TPA
- MDW
1 stop6h 25m
Frontier
Deal found 5/9![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/912:27 pm
MDW
- TPA
1 stop5h 24m
Frontier
Wed 6/177:45 am
TPA
- MDW
2 stops15h 26m
Frontier
Deal found 5/5![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 6/301:29 pm
ORD
- TPA
1 stop6h 48m
Frontier
Tue 7/72:25 pm
TPA
- ORD
1 stop6h 28m
Frontier
Deal found 5/6![Frontier logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
MDW
- TPA
1 stop14h 17m
Frontier
Fri 7/32:25 pm
TPA
- MDW
1 stop8h 46m
Frontier
Deal found 5/7![Frontier logo]()
$162
This American Airlines deal was found by Cheapflights users on 5/6. 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 6/306:10 pm
ORD
- TPA
Nonstop2h 42m
American Airlines
Tue 7/76:44 am
TPA
- ORD
Nonstop3h 05m
American Airlines
Deal found 5/6![American Airlines logo]()
$169
This Southwest deal was found by Cheapflights users on 5/6. 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 6/305:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Tue 6/309:55 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/6![Southwest logo]()
$169
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 May 10, 2026.
Search for one-way flight options from Chicago to Clearwater Beach. Find affordable one-way fares based on user searches. Data last updated May 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/16:00 am
MDW
- TPA
1 stop11h 51m
Frontier
Deal found 5/5![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 5/306:55 am
ORD
- TPA
1 stop9h 52m
Frontier
Deal found 5/6![Frontier logo]()
$84
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/305:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 5/7![Southwest logo]()
$85
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:30 pm
ORD
- TPA
Nonstop2h 54m
United Airlines
Deal found 5/8![United Airlines logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/712:11 pm
MDW
- TPA
1 stop22h 29m
Frontier
Deal found 5/9![Frontier logo]()
$88
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:40 am
MDW
- TPA
1 stop3h 50m
Southwest
Deal found 5/8![Southwest logo]()
$90
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/88:40 am
ORD
- TPA
1 stop5h 35m
United Airlines
Deal found 5/7![United Airlines logo]()
$90
This Trip.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
MDW
- TPA
1 stop10h 44m
Frontier
Deal found 5/9![Frontier logo]()
$91
This Expedia deal was found by Cheapflights users on 5/6. 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.
Fri 10/308:00 am
ORD
- TPA
Nonstop2h 58m
Frontier
Deal found 5/6![Frontier logo]()
$91
This Trip.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
MDW
- TPA
1 stop14h 27m
Frontier
Deal found 5/9![Frontier logo]()
$92
This Trip.com deal was found by Cheapflights users on 5/6. 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 5/286:55 am
ORD
- TPA
1 stop10h 56m
Frontier
Deal found 5/6![Frontier logo]()
$92
This Trip.com deal was found by Cheapflights users on 5/5. 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 7/156:00 am
MDW
- TPA
1 stop11h 52m
Frontier
Deal found 5/5![Frontier logo]()
$93
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 May 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $159 (Kiwi.com) |
One-way from | $84 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $252 |
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 May 10, 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 9/2
7:30 am-11:00 am
Nonstop2h 30m
Tampa
Wed 9/9
2:45 pm-7:05 pm
1 stop5h 20m
$179
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Wed 8/5
7:40 am-2:50 pm
2 stops6h 10m
Tampa
Wed 8/12
7:00 pm-10:20 pm
1 stop4h 20m
$194
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Wed 9/2
1:15 pm-8:04 pm
1 stop5h 49m
Tampa
Wed 9/30
7:59 pm-11:57 pm
1 stop4h 58m
$197
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Tue 6/30
8:40 am-3:25 pm
1 stop5h 45m
Tampa
Tue 7/7
7:42 pm-9:53 pm
Nonstop3h 11m
$197
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Tue 6/9
9:48 am-3:27 pm
1 stop4h 39m
Tampa
Tue 6/16
7:57 pm-11:59 pm
1 stop5h 02m
$197
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Sat 8/29
4:20 pm-8:16 pm
Nonstop2h 56m
Tampa
Sat 9/5
7:30 am-9:33 am
Nonstop3h 03m
$199
Quickest round-trip
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Wed 6/17
8:15 pm-11:50 pm
Nonstop2h 35m
Tampa
Wed 6/24
9:55 pm-11:35 pm
Nonstop2h 40m
$205
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Tue 6/2
11:26 am-5:41 pm
1 stop5h 15m
Tampa
Mon 6/8
7:57 pm-11:59 pm
1 stop5h 02m
$208
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Thu 5/28
11:26 am-6:51 pm
1 stop6h 25m
Tampa
Tue 6/2
5:46 pm-10:27 pm
1 stop5h 41m
$208
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Wed 9/2
11:00 am-2:56 pm
Nonstop2h 56m
Tampa
Wed 9/9
5:32 pm-11:17 pm
1 stop6h 45m
$209
Showing 1-10 of 47 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 May 10, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 14% on flights from Chicago to Clearwater Beach by exploring options for tickets in the afternoon.
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 May 9, 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.
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 May 10, 2026.
The most flights from CHI to CW9 are scheduled on a Saturday (79 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (39 on average).
How much does it cost to fly round-trip from Chicago to Clearwater Beach?
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 May 10, 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.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
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 Beach. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Popular flights
Alternative routes for Chicago to Clearwater Beach
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Clearwater Beach by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Clearwater Beach by cabin class
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 May 10, 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 May 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 8 airlines flying from Chicago to Clearwater Beach
Discover the top 8 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 May 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$48 | Average$199 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$77 | Average$178 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$98 | Average$359 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$105 | Average$220 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$147 | Average$288 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$356 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$156 | Average$356 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$358 | FlexibilityNo cancel fee | On-time69% |