$69+ Cheap flights from Chicago (CHI) to Clearwater, FL
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
May 1 — May 81
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Clearwater with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Clearwater are usually found in September or October, booked 29 days in advance, depart on a Thursday or Saturday and return on a Thursday
Cheap flight deals from Chicago to Clearwater
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Best
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Cheapest flights from Chicago to ClearwaterExplore the most affordable flight options available from Chicago to Clearwater. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.
Explore the most affordable flight options available from Chicago to Clearwater. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1311:25 am
ORD
- TPA
Nonstop2h 44m
Spirit Airlines
Thu 4/168:31 pm
TPA
- ORD
1 stop4h 53m
Spirit Airlines
Deal found 3/28![Spirit Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Tue 4/144:36 pm
ORD
- TPA
1 stop5h 42m
Multiple Airlines
Fri 4/179:51 pm
TPA
- ORD
Nonstop3h 07m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$127
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/288:52 pm
ORD
- TPA
Nonstop2h 37m
Spirit Airlines
Tue 5/510:21 am
TPA
- ORD
Nonstop3h 02m
Spirit Airlines
Deal found 3/27![Spirit Airlines logo]()
$128
This CheapOair deal was found by Cheapflights users on 3/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/128:30 am
ORD
- TPA
Nonstop2h 39m
Multiple Airlines
Sun 5/177:18 am
TPA
- ORD
Nonstop3h 09m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$129
This Mytrip deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:15 pm
ORD
- TPA
2 stops20h 42m
Spirit Airlines
Wed 4/228:31 pm
TPA
- ORD
1 stop4h 53m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$130
This Spirit deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:28 am
ORD
- TPA
1 stop4h 29m
Spirit Airlines
Mon 4/204:18 pm
TPA
- ORD
Nonstop3h 02m
Spirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$131
This Cheapflightsfares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:25 am
ORD
- TPA
Nonstop2h 48m
Frontier
Mon 4/2010:55 pm
TPA
- ORD
Nonstop3h 14m
Frontier
Deal found 3/30![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/142:15 pm
MDW
- TPA
1 stop9h 11m
Multiple Airlines
Fri 4/176:02 pm
TPA
- MDW
1 stop5h 24m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$132
This Priceline deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1811:45 am
ORD
- TPA
Nonstop2h 54m
Multiple Airlines
Tue 4/214:18 pm
TPA
- ORD
Nonstop3h 02m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/1711:28 am
ORD
- TPA
1 stop4h 29m
Multiple Airlines
Sun 4/196:02 pm
TPA
- ORD
1 stop18h 30m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/187:34 pm
MDW
- TPA
1 stop20h 23m
Multiple Airlines
Tue 4/216:02 pm
TPA
- MDW
1 stop5h 12m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1311:25 am
ORD
- TPA
Nonstop2h 44m
Multiple Airlines
Tue 4/148:14 am
TPA
- ORD
1 stop14h 03m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$135
Best flights from Chicago to ClearwaterDiscover carefully curated flight deals from Chicago to Clearwater that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2026.
Discover carefully curated flight deals from Chicago to Clearwater that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2026.
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:40 am
MDW
- TPA
1 stop3h 50m
Southwest
Wed 5/201:35 pm
TPA
- MDW
1 stop4h 20m
Southwest
Deal found 3/30![Southwest logo]()
$184
This United Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/267:31 am
ORD
- TPA
Nonstop2h 53m
United Airlines
Wed 6/36:57 pm
TPA
- ORD
1 stop5h 29m
United Airlines
Deal found 3/31![United Airlines logo]()
$194
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/115:19 pm
ORD
- TPA
1 stop4h 57m
Delta
Wed 5/134:37 pm
TPA
- ORD
1 stop4h 49m
Delta
Deal found 3/31![Delta logo]()
$208
This United Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/128:45 am
ORD
- TPA
1 stop5h 43m
United Airlines
Sat 5/166:57 pm
TPA
- ORD
1 stop5h 47m
United Airlines
Deal found 3/31![United Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/163:30 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Mon 5/186:30 pm
TPA
- MDW
Nonstop2h 50m
Southwest
Deal found 3/29![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/127:40 am
MDW
- TPA
1 stop3h 50m
Southwest
Sat 5/166:10 pm
TPA
- MDW
1 stop5h 35m
Southwest
Deal found 3/31![Southwest logo]()
$199
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:19 pm
ORD
- TPA
1 stop4h 57m
Delta
Wed 5/271:45 pm
TPA
- ORD
1 stop7h 41m
Delta
Deal found 3/29![Delta logo]()
$219
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/95:19 pm
ORD
- TPA
1 stop4h 57m
Delta
Mon 5/183:16 pm
TPA
- ORD
1 stop6h 10m
Delta
Deal found 3/31![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 3/27. 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.
Wed 5/277:40 am
MDW
- TPA
1 stop3h 50m
Southwest
Wed 6/36:00 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Deal found 3/27![Southwest logo]()
$205
This Delta deal was found by Cheapflights users on 3/28. 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 6/35:30 am
ORD
- TPA
1 stop6h 10m
Delta
Wed 6/36:53 pm
TPA
- ORD
1 stop6h 15m
Delta
Deal found 3/28![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 3/27. 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.
Mon 5/118:30 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Mon 5/187:00 pm
TPA
- MDW
1 stop5h 55m
Southwest
Deal found 3/27![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 3/27. 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.
Sat 5/235:10 pm
MDW
- TPA
1 stop6h 19m
Delta
Wed 5/2711:01 am
TPA
- MDW
1 stop6h 11m
Delta
Deal found 3/27![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 6/18:30 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Thu 6/49:20 am
TPA
- MDW
1 stop5h 05m
Southwest
Deal found 3/31![Southwest logo]()
$209
This United Airlines deal was found by Cheapflights users on 3/28. 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.
Sun 5/317:31 am
ORD
- TPA
Nonstop2h 53m
United Airlines
Wed 6/37:27 pm
TPA
- ORD
Nonstop3h 11m
United Airlines
Deal found 3/28![United Airlines logo]()
$286
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:45 am
MDW
- TPA
1 stop6h 05m
Southwest
Mon 5/46:30 pm
TPA
- MDW
Nonstop2h 50m
Southwest
Deal found 3/30![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:45 pm
ORD
- TPA
1 stop7h 20m
Southwest
Mon 5/115:40 am
TPA
- ORD
2 stops10h 50m
Southwest
Deal found 3/30![Southwest logo]()
$224
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Sun 5/105:30 am
ORD
- TPA
1 stop5h 04m
Delta
Sun 5/176:53 pm
TPA
- ORD
1 stop6h 06m
Delta
Deal found 3/31![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1211:55 am
ORD
- TPA
2 stops9h 05m
Southwest
Wed 5/139:35 am
TPA
- ORD
2 stops9h 50m
Southwest
Deal found 3/29![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 3/27. 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 5/1611:50 am
ORD
- TPA
Nonstop2h 40m
Southwest
Sun 5/177:25 am
TPA
- ORD
1 stop6h 50m
Southwest
Deal found 3/27![Southwest logo]()
$238
This Southwest deal was found by Cheapflights users on 3/27. 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 5/147:45 am
MDW
- TPA
1 stop5h 30m
Southwest
Sun 5/177:25 pm
TPA
- MDW
1 stop6h 35m
Southwest
Deal found 3/27![Southwest logo]()
$248
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2111:10 am
MDW
- TPA
1 stop3h 45m
Southwest
Fri 4/246:30 pm
TPA
- MDW
Nonstop2h 50m
Southwest
Deal found 3/29![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2512:05 pm
MDW
- TPA
2 stops7h 10m
Southwest
Wed 4/291:45 pm
TPA
- MDW
2 stops6h 50m
Southwest
Deal found 3/31![Southwest logo]()
$288
Last-minute flights from Chicago to ClearwaterDiscover last-minute flight deals from Chicago to Clearwater. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Clearwater. Data last updated April 1, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 3/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1311:25 am
ORD
- TPA
Nonstop2h 44m
Spirit Airlines
Thu 4/168:31 pm
TPA
- ORD
1 stop4h 53m
Spirit Airlines
Deal found 3/28![Spirit Airlines logo]()
$126
This Cheapflightsfares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:25 am
ORD
- TPA
Nonstop2h 48m
Frontier
Mon 4/2010:55 pm
TPA
- ORD
Nonstop3h 14m
Frontier
Deal found 3/30![Frontier logo]()
$132
This Cheapflightsfares deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:17 am
ORD
- TPA
1 stop9h 24m
Spirit Airlines
Sat 4/184:18 pm
TPA
- ORD
Nonstop3h 02m
Spirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Tue 4/144:36 pm
ORD
- TPA
1 stop5h 42m
Multiple Airlines
Fri 4/179:51 pm
TPA
- ORD
Nonstop3h 07m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/144:36 pm
ORD
- TPA
1 stop5h 42m
Multiple Airlines
Fri 5/19:51 pm
TPA
- ORD
Nonstop3h 07m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/142:15 pm
MDW
- TPA
1 stop9h 11m
Multiple Airlines
Fri 4/176:02 pm
TPA
- MDW
1 stop5h 24m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$132
This Spirit deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:28 am
ORD
- TPA
1 stop4h 29m
Spirit Airlines
Mon 4/204:18 pm
TPA
- ORD
Nonstop3h 02m
Spirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/1711:28 am
ORD
- TPA
1 stop4h 29m
Multiple Airlines
Sun 4/196:02 pm
TPA
- ORD
1 stop18h 30m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$134
This Mytrip deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:15 pm
ORD
- TPA
2 stops20h 42m
Spirit Airlines
Wed 4/228:31 pm
TPA
- ORD
1 stop4h 53m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$130
This Priceline deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1811:45 am
ORD
- TPA
Nonstop2h 54m
Multiple Airlines
Tue 4/214:18 pm
TPA
- ORD
Nonstop3h 02m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/187:34 pm
MDW
- TPA
1 stop20h 23m
Multiple Airlines
Tue 4/216:02 pm
TPA
- MDW
1 stop5h 12m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$134
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/288:52 pm
ORD
- TPA
Nonstop2h 37m
Spirit Airlines
Tue 5/510:21 am
TPA
- ORD
Nonstop3h 02m
Spirit Airlines
Deal found 3/27![Spirit Airlines logo]()
$128
One-way flights from Chicago to ClearwaterSearch for one-way flight options from Chicago to Clearwater. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
Search for one-way flight options from Chicago to Clearwater. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:28 am
ORD
- TPA
1 stop4h 29m
Spirit Airlines
Deal found 3/29![Spirit Airlines logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:16 am
ORD
- TPA
1 stop14h 10m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/142:15 pm
MDW
- TPA
1 stop9h 11m
Frontier
Deal found 3/31![Frontier logo]()
$71
This Mytrip deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:15 pm
ORD
- TPA
2 stops20h 42m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Tue 4/286:10 am
MDW
- TPA
1 stop9h 47m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$72
This Cheapflightsfares deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:28 am
ORD
- TPA
1 stop4h 29m
Spirit Airlines
Deal found 3/29![Spirit Airlines logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:34 pm
MDW
- TPA
1 stop11h 00m
Frontier
Deal found 3/28![Frontier logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2911:28 am
ORD
- TPA
1 stop21h 36m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$73
This WAYA deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:15 pm
MDW
- TPA
1 stop9h 11m
Frontier
Deal found 3/30![Frontier logo]()
$74
This WAYA deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Thu 4/304:28 pm
ORD
- TPA
1 stop6h 58m
Frontier
Deal found 3/31![Frontier logo]()
$74
This Super.com deal was found by Cheapflights users on 3/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:34 pm
MDW
- TPA
1 stop11h 00m
Frontier
Deal found 3/27![Frontier logo]()
$75
This WAYA deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/156:08 pm
ORD
- TPA
1 stop5h 18m
Frontier
Deal found 3/31![Frontier logo]()
$75
Find flight deals from Chicago to Clearwater
Keep the following information in mind while searching for Chicago to Clearwater flight deals. Data was last updated April 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $126 (Cheapflightsfares) |
One-way from | $69 (Cheapflightsfares) |
Popular in | December |
Cheapest in | September |
Average price | $234 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Clearwater that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 1, 2026.
Use the filters below to find and compare flights from Chicago to Clearwater that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Wed 5/13
7:40 am-12:30 pm
1 stop3h 50m
Tampa
Wed 5/20
1:35 pm-4:55 pm
1 stop4h 20m
$184
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Tue 5/26
7:31 am-11:24 am
Nonstop2h 53m
Tampa
Wed 6/3
6:57 pm-11:26 pm
1 stop5h 29m
$194
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Tue 5/12
8:45 am-3:28 pm
1 stop5h 43m
Tampa
Sat 5/16
6:57 pm-11:44 pm
1 stop5h 47m
$199
Quickest round-trip
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 5/16
3:30 pm-7:05 pm
Nonstop2h 35m
Tampa
Mon 5/18
6:30 pm-8:20 pm
Nonstop2h 50m
$199
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Tue 5/12
7:40 am-12:30 pm
1 stop3h 50m
Tampa
Sat 5/16
6:10 pm-10:45 pm
1 stop5h 35m
$199
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Wed 5/27
7:40 am-12:30 pm
1 stop3h 50m
Tampa
Wed 6/3
6:00 pm-7:45 pm
Nonstop2h 45m
$205
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Mon 5/11
5:19 pm-11:16 pm
1 stop4h 57m
Tampa
Wed 5/13
4:37 pm-8:26 pm
1 stop4h 49m
$208
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Mon 5/11
8:30 pm-12:05 am
Nonstop2h 35m
Tampa
Mon 5/18
7:00 pm-11:55 pm
1 stop5h 55m
$209
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Mon 6/1
8:30 pm-12:05 am
Nonstop2h 35m
Tampa
Thu 6/4
9:20 am-1:25 pm
1 stop5h 05m
$209
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 5/2
7:45 am-2:50 pm
1 stop6h 05m
Tampa
Mon 5/4
6:30 pm-8:20 pm
Nonstop2h 50m
$209
Showing 1-10 of 46 resultsSorted by cheapest first
Best time to book a flight from Chicago to Clearwater
Have a flexible travel schedule? Discover the best time to fly to Clearwater from Chicago with our price prediction graph.
ORD-TPA
MDW-TPA
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Clearwater
CHI-CL9
ORD-TPA
MDW-TPA
How far ahead should I book a flight from Chicago to Clearwater?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Clearwater. Price data was last updated on March 13, 2026.
The price you pay for your flight from Chicago to Clearwater may vary depending on when you book. For the best chance of a lower fare, look to book 29 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Chicago to Clearwater?
Currently, March is the cheapest month in which you can book a flight from Chicago to Clearwater (average of $56). Flying from Chicago to Clearwater in April is currently the most expensive (average of $91). 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 CL9?
Find hourly flight availability from Chicago to Clearwater. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 1, 2026.
It’s typically best to fly out from Chicago to Clearwater in the afternoon. Doing so could potentially save you 14% on the flight price compared to flying at noon, which is usually more expensive.
What is the cheapest day to fly from Chicago to Clearwater?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Clearwater. Price data was last updated on March 28, 2026.
Travelers seeking maximum savings on their Chicago to Clearwater flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Clearwater
Explore weekly flight availability from Chicago to Clearwater. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 1, 2026.
The most flights from CHI to CL9 are scheduled on a Tuesday (77 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 on average).
How much does it cost to fly round-trip from Chicago to Clearwater?
Reviews of airlines servicing Clearwater
Get insights into the airlines that provide service to Clearwater. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Clearwater. Reviews last updated April 1, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Clearwater to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
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. 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.
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Alternative routes for Chicago to Clearwater
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Clearwater by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Clearwater by cabin class
Find flights from Chicago to Clearwater, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Clearwater flights
Browse other Chicago and Clearwater flight options. Last updated on April 1, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on April 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Clearwater flights
Consider these flights traveling from Chicago to Clearwater.
Top 8 airlines flying from Chicago to Clearwater
Discover the top 8 airlines that operate flights from Chicago to Clearwater. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$48 | Average$199 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$76 | Average$175 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$87 | Average$217 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$98 | Average$405 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$312 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$153 | Average$355 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$156 | Average$358 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$353 | FlexibilityNo cancel fee | On-time69% |