$63+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
4月 11 — 4月 181
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Clearwater Beach with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Clearwater Beach are usually found in September or October, booked 29 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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Best
Last-minute
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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 3月 12, 2026.
Explore the most affordable flight options available from Chicago to Clearwater Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3月 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/7. 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.
週三 4/156:08 pm
ORD
- TPA
1 stop5h 18m
Frontier
週一 4/2010:55 pm
TPA
- ORD
Nonstop3h 14m
Frontier
Deal found 3/7![Frontier logo]()
$121
This Cheapflightsfares deal was found by Cheapflights users on 3/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 5/1612:53 pm
ORD
- TPA
Nonstop2h 56m
Frontier
週六 5/2312:08 pm
TPA
- ORD
Nonstop3h 11m
Frontier
Deal found 3/7![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
週二 4/286:08 pm
ORD
- TPA
1 stop5h 18m
Frontier
週二 5/58:44 am
TPA
- ORD
1 stop14h 55m
Frontier
Deal found 3/9![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
週三 4/292:15 pm
MDW
- TPA
1 stop9h 11m
Frontier
週一 5/47:50 pm
TPA
- MDW
1 stop27h 12m
Frontier
Deal found 3/10![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
週六 4/184:28 pm
ORD
- TPA
1 stop6h 58m
Frontier
週一 4/2010:55 pm
TPA
- ORD
Nonstop3h 14m
Frontier
Deal found 3/9![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
週六 4/257:59 pm
ORD
- TPA
Nonstop3h 00m
Multiple Airlines
週一 5/43:10 pm
TPA
- ORD
Nonstop3h 00m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 5/64:28 pm
ORD
- TPA
1 stop6h 58m
Frontier
週二 5/128:44 am
TPA
- ORD
1 stop14h 55m
Frontier
Deal found 3/8![Frontier logo]()
$126
This Cheapflightsfares deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 4/135:25 am
ORD
- TPA
Nonstop2h 48m
Frontier
週五 4/2410:13 pm
TPA
- ORD
Nonstop3h 14m
Frontier
Deal found 3/11![Frontier logo]()
$127
This Expedia deal was found by Cheapflights users on 3/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 4/193:08 pm
ORD
- TPA
Nonstop2h 59m
Multiple Airlines
週三 4/224:18 pm
TPA
- ORD
Nonstop3h 02m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$128
This CheapOair deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 4/65:25 am
ORD
- TPA
Nonstop2h 48m
Multiple Airlines
週二 4/1410:54 pm
TPA
- ORD
1 stop11h 42m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
週日 4/125:25 am
ORD
- TPA
Nonstop2h 48m
Frontier
週五 4/175:30 am
TPA
- ORD
1 stop7h 07m
Frontier
Deal found 3/10![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
週六 5/94:28 pm
ORD
- TPA
1 stop6h 58m
Frontier
週一 5/119:51 pm
TPA
- ORD
Nonstop3h 07m
Frontier
Deal found 3/10![Frontier logo]()
$131
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 3月 12, 2026.
Discover carefully curated flight deals from Chicago to Clearwater Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 3月 12, 2026.
This United Airlines deal was found by Cheapflights users on 3/8. 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.
週六 5/1612:55 pm
ORD
- TPA
1 stop7h 02m
United Airlines
週六 5/237:27 pm
TPA
- ORD
Nonstop3h 11m
United Airlines
Deal found 3/8![United Airlines logo]()
$173
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 4/255:55 pm
MDW
- TPA
Nonstop2h 35m
Southwest
週六 5/99:00 am
TPA
- MDW
Nonstop2h 45m
Southwest
Deal found 3/9![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 3/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 4/255:59 pm
ORD
- TPA
1 stop5h 27m
Delta
週二 4/284:55 pm
TPA
- ORD
1 stop6h 26m
Delta
Deal found 3/7![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 4/155:55 am
MDW
- TPA
Nonstop2h 30m
Southwest
週三 4/223:55 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Deal found 3/11![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 4/183:30 pm
MDW
- TPA
Nonstop2h 35m
Southwest
週一 4/2011:00 am
TPA
- MDW
1 stop5h 50m
Southwest
Deal found 3/9![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 3/8. 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.
週日 4/198:00 am
ORD
- TPA
1 stop15h 40m
Southwest
週六 4/258:25 am
TPA
- ORD
2 stops8h 05m
Southwest
Deal found 3/8![Southwest logo]()
$213
This Delta deal was found by Cheapflights users on 3/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 5/177:00 am
ORD
- TPA
1 stop4h 47m
Delta
週六 5/235:49 pm
TPA
- ORD
1 stop4h 57m
Delta
Deal found 3/7![Delta logo]()
$258
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 4/256:00 am
ORD
- TPA
2 stops12h 40m
Southwest
週六 5/98:25 am
TPA
- ORD
2 stops8h 05m
Southwest
Deal found 3/9![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週四 5/215:56 pm
ORD
- TPA
Nonstop2h 53m
United Airlines
週一 5/257:35 am
TPA
- ORD
Nonstop3h 10m
United Airlines
Deal found 3/11![United Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 4/222:00 pm
ORD
- TPA
Nonstop2h 50m
Southwest
週日 4/2610:55 pm
TPA
- ORD
2 stops14h 55m
Southwest
Deal found 3/9![Southwest logo]()
$258
This Southwest deal was found by Cheapflights users on 3/8. 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.
週五 4/36:30 pm
MDW
- TPA
Nonstop2h 35m
Southwest
週三 4/86:10 am
TPA
- MDW
1 stop6h 25m
Southwest
Deal found 3/8![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 3/8. 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.
週二 3/243:35 pm
MDW
- TPA
1 stop4h 15m
Southwest
週二 3/317:00 am
TPA
- MDW
Nonstop2h 50m
Southwest
Deal found 3/8![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週四 4/168:30 pm
MDW
- TPA
Nonstop2h 35m
Southwest
週四 4/233:35 pm
TPA
- MDW
1 stop5h 55m
Southwest
Deal found 3/10![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 4/512:30 pm
MDW
- TPA
1 stop4h 05m
Southwest
週三 4/82:35 pm
TPA
- MDW
1 stop6h 30m
Southwest
Deal found 3/9![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 6/105:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
週一 6/158:00 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 3/10![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 3/8. 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.
週二 3/244:45 pm
MDW
- TPA
1 stop4h 15m
Southwest
週一 3/308:20 pm
TPA
- MDW
1 stop4h 45m
Southwest
Deal found 3/8![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週五 4/105:40 pm
MDW
- TPA
1 stop4h 20m
Southwest
週一 4/135:40 am
TPA
- MDW
1 stop5h 45m
Southwest
Deal found 3/10![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 4/16:15 am
ORD
- TPA
2 stops12h 05m
Southwest
週三 4/810:10 am
TPA
- ORD
2 stops9h 15m
Southwest
Deal found 3/11![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 4/132:00 pm
ORD
- TPA
Nonstop2h 50m
Southwest
週四 4/162:00 pm
TPA
- ORD
Nonstop3h 05m
Southwest
Deal found 3/11![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 6/106:00 am
ORD
- TPA
2 stops14h 15m
Southwest
週一 6/157:15 am
TPA
- ORD
1 stop7h 15m
Southwest
Deal found 3/10![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週五 4/106:15 am
ORD
- TPA
2 stops13h 30m
Southwest
週一 4/139:50 pm
TPA
- ORD
2 stops16h 00m
Southwest
Deal found 3/9![Southwest logo]()
$341
Last-minute flights from Chicago to Clearwater BeachDiscover last-minute flight deals from Chicago to Clearwater Beach. Data last updated 3月 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Clearwater Beach. Data last updated 3月 12, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 4/65:25 am
ORD
- TPA
Nonstop2h 48m
Multiple Airlines
週二 4/1410:54 pm
TPA
- ORD
1 stop11h 42m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
週二 4/77:17 am
ORD
- TPA
1 stop9h 24m
Multiple Airlines
週二 4/147:50 pm
TPA
- ORD
1 stop15h 12m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$132
This Super.com deal was found by Cheapflights users on 3/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 4/119:32 am
ORD
- TPA
Nonstop2h 54m
Frontier
週一 4/2010:55 pm
TPA
- ORD
Nonstop3h 14m
Frontier
Deal found 3/9![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
週日 4/125:25 am
ORD
- TPA
Nonstop2h 48m
Frontier
週五 4/175:30 am
TPA
- ORD
1 stop7h 07m
Frontier
Deal found 3/10![Frontier logo]()
$130
This Cheapflightsfares deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週一 4/135:25 am
ORD
- TPA
Nonstop2h 48m
Frontier
週五 4/2410:13 pm
TPA
- ORD
Nonstop3h 14m
Frontier
Deal found 3/11![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 3/7. 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.
週三 4/156:08 pm
ORD
- TPA
1 stop5h 18m
Frontier
週一 4/2010:55 pm
TPA
- ORD
Nonstop3h 14m
Frontier
Deal found 3/7![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
週六 4/184:28 pm
ORD
- TPA
1 stop6h 58m
Frontier
週一 4/2010:55 pm
TPA
- ORD
Nonstop3h 14m
Frontier
Deal found 3/9![Frontier logo]()
$124
This Expedia deal was found by Cheapflights users on 3/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 4/193:08 pm
ORD
- TPA
Nonstop2h 59m
Multiple Airlines
週三 4/224:18 pm
TPA
- ORD
Nonstop3h 02m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
週六 4/257:59 pm
ORD
- TPA
Nonstop3h 00m
Multiple Airlines
週一 5/43:10 pm
TPA
- ORD
Nonstop3h 00m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
週六 4/257:59 pm
ORD
- TPA
Nonstop3h 00m
Multiple Airlines
週六 5/93:53 pm
TPA
- ORD
1 stop6h 24m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
週二 4/286:08 pm
ORD
- TPA
1 stop5h 18m
Frontier
週二 5/58:44 am
TPA
- ORD
1 stop14h 55m
Frontier
Deal found 3/9![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
週三 4/292:15 pm
MDW
- TPA
1 stop9h 11m
Frontier
週一 5/47:50 pm
TPA
- MDW
1 stop27h 12m
Frontier
Deal found 3/10![Frontier logo]()
$123
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 3月 12, 2026.
Search for one-way flight options from Chicago to Clearwater Beach. Find affordable one-way fares based on user searches. Data last updated 3月 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 4/1811:45 am
ORD
- TPA
Nonstop2h 54m
Frontier
Deal found 3/8![Frontier logo]()
$63
This Frontier deal was found by Cheapflights users on 3/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週二 3/243:28 pm
ORD
- TPA
Nonstop2h 56m
Frontier
Deal found 3/8![Frontier logo]()
$64
This Trip.com deal was found by Cheapflights users on 3/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 5/166:00 am
MDW
- TPA
1 stop17h 26m
Frontier
Deal found 3/8![Frontier logo]()
$64
This Cheapflightsfares deal was found by Cheapflights users on 3/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 4/87:17 am
ORD
- TPA
1 stop9h 24m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
週六 4/187:34 pm
MDW
- TPA
1 stop11h 00m
Frontier
Deal found 3/9![Frontier logo]()
$65
This Trip.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週二 5/51:59 pm
ORD
- TPA
1 stop6h 28m
Frontier
Deal found 3/11![Frontier logo]()
$66
This eDestinos deal was found by Cheapflights users on 3/9. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週二 5/194:28 pm
ORD
- TPA
1 stop14h 06m
Frontier
Deal found 3/9![Frontier logo]()
$67
This eDestinos deal was found by Cheapflights users on 3/9. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週二 5/192:20 pm
MDW
- TPA
1 stop9h 06m
Frontier
Deal found 3/9![Frontier logo]()
$67
This Cheapflightsfares deal was found by Cheapflights users on 3/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 4/49:32 am
ORD
- TPA
Nonstop2h 54m
Frontier
Deal found 3/9![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週二 4/142:15 pm
MDW
- TPA
1 stop9h 11m
Frontier
Deal found 3/11![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週六 4/259:16 am
ORD
- TPA
1 stop21h 18m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週三 5/611:51 am
ORD
- TPA
1 stop8h 36m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$72
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 3月 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $121 (Kiwi.com) |
One-way from | $63 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $292 |
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 3月 12, 2026.
Use the filters below to find and compare flights from Chicago to Clearwater Beach that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
週六 5/16
12:55 pm-8:57 pm
1 stop7h 02m
Tampa
週六 5/23
7:27 pm-9:38 pm
Nonstop3h 11m
$173
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
週六 4/25
5:55 pm-9:30 pm
Nonstop2h 35m
Tampa
週六 5/9
9:00 am-10:45 am
Nonstop2h 45m
$197
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
週六 4/25
5:59 pm-12:26 am
1 stop5h 27m
Tampa
週二 4/28
4:55 pm-10:21 pm
1 stop6h 26m
$197
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
週三 4/15
5:55 am-9:25 am
Nonstop2h 30m
Tampa
週三 4/22
3:55 pm-5:40 pm
Nonstop2h 45m
$197
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
週六 4/18
3:30 pm-7:05 pm
Nonstop2h 35m
Tampa
週一 4/20
11:00 am-3:50 pm
1 stop5h 50m
$207
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
週日 4/19
8:00 am-12:40 am
1 stop15h 40m
Tampa
週六 4/25
8:25 am-3:30 pm
2 stops8h 05m
$213
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
週六 4/25
6:00 am-7:40 pm
2 stops12h 40m
Tampa
週六 5/9
8:25 am-3:30 pm
2 stops8h 05m
$227
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
週日 5/17
7:00 am-12:47 pm
1 stop4h 47m
Tampa
週六 5/23
5:49 pm-9:46 pm
1 stop4h 57m
$258
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
週三 4/22
2:00 pm-5:50 pm
Nonstop2h 50m
Tampa
週日 4/26
10:55 pm-12:50 pm
2 stops14h 55m
$258
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
週五 4/3
6:30 pm-10:05 pm
Nonstop2h 35m
Tampa
週三 4/8
6:10 am-11:35 am
1 stop6h 25m
$267
Showing 1-10 of 45 resultsSorted by cheapest first
Best time to book a flight from Chicago to Clearwater Beach
Have a flexible travel schedule? Discover the best time to fly to Clearwater Beach from Chicago with our price prediction graph.
ORD-TPA
MDW-TPA
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Clearwater Beach
CHI-CW9
ORD-TPA
MDW-TPA
How far ahead should I book a flight from Chicago to Clearwater Beach?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Clearwater Beach. Price data was last updated on March 6, 2026.
The best time to book flights from Chicago to Clearwater Beach is 29 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago to Clearwater Beach?
Currently, March is the cheapest month in which you can book a flight from Chicago to Clearwater Beach (average of $56). Flying from Chicago to Clearwater Beach in December is currently the most expensive (average of $89). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 3月 12, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 12% 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 February 21, 2026.
Travelers seeking maximum savings on their Chicago to Clearwater Beach flight should consider departing on Wednesday evenings 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 3月 12, 2026.
The most flights from CHI to CW9 are scheduled on a Thursday (76 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (47 on average).
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 3月 12, 2026.
Read through reviews of airlines operating flights from Chicago to Clearwater Beach, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Clearwater 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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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 Beach
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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 3月 12, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on 3月 12, 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 3月 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$48 | Average$190 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$74 | Average$173 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$82 | Average$208 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$98 | Average$411 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$288 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$155 | Average$350 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$156 | Average$352 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$156 | Average$354 | FlexibilityNo cancel fee | On-time71% |