$85+ Cheap flights from Chicago (CHI) to Clearwater, FL
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jun 12 — Jun 191
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 30 days in advance, depart on a Wednesday or Saturday and return on a Friday
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 May 13, 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 May 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Sun 11/18:00 am
ORD
- TPA
Nonstop2h 58m
Frontier
Thu 11/51:05 pm
TPA
- ORD
Nonstop3h 21m
Frontier
Deal found 5/11![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 5/9. 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 5/11. 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.
Wed 7/16:00 am
MDW
- TPA
1 stop14h 17m
Frontier
Sat 7/41:18 pm
TPA
- MDW
1 stop9h 53m
Frontier
Deal found 5/11![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 5/271:50 pm
ORD
- TPA
1 stop6h 37m
Frontier
Tue 6/22:25 pm
TPA
- ORD
1 stop6h 04m
Frontier
Deal found 5/12![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Wed 6/312:04 pm
MDW
- TPA
1 stop5h 47m
Frontier
Tue 6/94:46 pm
TPA
- MDW
1 stop6h 25m
Frontier
Deal found 5/11![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Wed 5/2712:04 pm
MDW
- TPA
1 stop8h 23m
Frontier
Tue 6/24:46 pm
TPA
- MDW
1 stop6h 16m
Frontier
Deal found 5/11![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Sat 6/66:55 am
ORD
- TPA
1 stop9h 52m
Frontier
Tue 6/162:25 pm
TPA
- ORD
1 stop6h 25m
Frontier
Deal found 5/11![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/11:50 pm
ORD
- TPA
1 stop20h 49m
Frontier
Mon 6/82:25 pm
TPA
- ORD
1 stop6h 04m
Frontier
Deal found 5/12![Frontier logo]()
$168
This American Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Wed 8/56:19 pm
ORD
- TPA
Nonstop2h 47m
American Airlines
Wed 8/126:19 am
TPA
- ORD
Nonstop3h 11m
American Airlines
Deal found 5/13![American Airlines logo]()
$169
This Southwest deal was found by Cheapflights users on 5/11. 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.
Wed 7/18:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Wed 7/86:55 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/11![Southwest logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Wed 6/1712:04 pm
MDW
- TPA
1 stop8h 13m
Frontier
Wed 6/244:46 pm
TPA
- MDW
1 stop6h 25m
Frontier
Deal found 5/11![Frontier logo]()
$170
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 May 13, 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 May 13, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/238:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Wed 6/249:55 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/9![Southwest logo]()
$169
This Delta deal was found by Cheapflights users on 5/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:27 pm
MDW
- TPA
1 stop6h 52m
Delta
Sat 9/56:15 am
TPA
- MDW
1 stop7h 15m
Delta
Deal found 5/11![Delta logo]()
$219
This United Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/25:56 pm
ORD
- TPA
Nonstop2h 53m
United Airlines
Sat 6/67:42 pm
TPA
- ORD
Nonstop3h 11m
United Airlines
Deal found 5/12![United Airlines logo]()
$244
This Southwest deal was found by Cheapflights users on 5/11. 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.
Tue 6/162:35 pm
MDW
- TPA
1 stop6h 55m
Southwest
Wed 6/249:55 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/11![Southwest logo]()
$215
This Delta deal was found by Cheapflights users on 5/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/65:30 am
ORD
- TPA
1 stop5h 04m
Delta
Wed 7/85:15 am
TPA
- ORD
1 stop4h 20m
Delta
Deal found 5/11![Delta logo]()
$254
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/47:35 am
MDW
- TPA
Nonstop2h 35m
Southwest
Sat 7/119:20 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/9![Southwest logo]()
$241
This United Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 7/227:31 am
ORD
- TPA
Nonstop2h 53m
United Airlines
Thu 8/67:50 am
TPA
- ORD
Nonstop3h 10m
United Airlines
Deal found 5/12![United Airlines logo]()
$266
This Delta deal was found by Cheapflights users on 5/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:30 am
ORD
- TPA
1 stop5h 04m
Delta
Sun 7/55:15 am
TPA
- ORD
1 stop5h 58m
Delta
Deal found 5/11![Delta logo]()
$264
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 6/248:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Sat 6/277:50 pm
TPA
- MDW
1 stop4h 25m
Southwest
Deal found 5/8![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/25:56 pm
ORD
- TPA
Nonstop2h 53m
United Airlines
Fri 6/56:57 pm
TPA
- ORD
1 stop5h 29m
United Airlines
Deal found 5/12![United Airlines logo]()
$281
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.
Sat 5/305:55 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Mon 6/13:55 pm
TPA
- MDW
1 stop5h 40m
Southwest
Deal found 5/8![Southwest logo]()
$250
This Southwest deal was found by Cheapflights users on 5/11. 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.
Wed 8/267:40 am
MDW
- TPA
2 stops6h 10m
Southwest
Mon 8/3111:30 am
TPA
- MDW
1 stop4h 00m
Southwest
Deal found 5/11![Southwest logo]()
$251
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.
Mon 7/65:30 am
ORD
- TPA
1 stop6h 15m
Delta
Sat 7/115:15 am
TPA
- ORD
1 stop5h 51m
Delta
Deal found 5/9![Delta logo]()
$306
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 6/172:30 pm
ORD
- TPA
Nonstop2h 54m
United Airlines
Sun 6/218:00 am
TPA
- ORD
Nonstop3h 10m
United Airlines
Deal found 5/8![United Airlines logo]()
$309
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/207:45 am
MDW
- TPA
Nonstop2h 40m
Southwest
Tue 6/239:55 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/9![Southwest logo]()
$256
This United Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 5/166:20 pm
ORD
- TPA
Nonstop2h 57m
United Airlines
Mon 5/186:57 pm
TPA
- ORD
1 stop5h 47m
United Airlines
Deal found 5/12![United Airlines logo]()
$329
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:50 am
MDW
- TPA
2 stops7h 00m
Southwest
Fri 10/309:25 am
TPA
- MDW
1 stop5h 35m
Southwest
Deal found 5/10![Southwest logo]()
$275
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.
Thu 7/98:40 am
ORD
- TPA
1 stop5h 35m
United Airlines
Mon 7/136:57 pm
TPA
- ORD
1 stop5h 34m
United Airlines
Deal found 5/8![United Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:30 am
MDW
- TPA
2 stops6h 50m
Southwest
Wed 7/229:05 am
TPA
- MDW
1 stop6h 15m
Southwest
Deal found 5/12![Southwest logo]()
$281
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/275:50 pm
MDW
- TPA
1 stop4h 40m
Southwest
Wed 7/19:55 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/10![Southwest logo]()
$285
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1911:55 am
ORD
- TPA
2 stops9h 05m
Southwest
Wed 5/277:55 pm
TPA
- ORD
2 stops17h 55m
Southwest
Deal found 5/9![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 5/11. 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.
Thu 5/282:00 pm
ORD
- TPA
Nonstop2h 50m
Southwest
Mon 6/12:00 pm
TPA
- ORD
Nonstop3h 05m
Southwest
Deal found 5/11![Southwest logo]()
$322
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:55 pm
ORD
- TPA
1 stop5h 10m
Southwest
Wed 5/277:55 pm
TPA
- ORD
2 stops17h 55m
Southwest
Deal found 5/10![Southwest logo]()
$333
Last-minute flights from Chicago to ClearwaterDiscover last-minute flight deals from Chicago to Clearwater. Data last updated May 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Clearwater. Data last updated May 13, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 5/271:50 pm
ORD
- TPA
1 stop6h 37m
Frontier
Tue 6/22:25 pm
TPA
- ORD
1 stop6h 04m
Frontier
Deal found 5/12![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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
Tue 6/24:46 pm
TPA
- MDW
1 stop6h 16m
Frontier
Deal found 5/12![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 5/10. 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.
Sat 5/306:55 am
ORD
- TPA
1 stop9h 52m
Frontier
Wed 6/32:25 pm
TPA
- ORD
1 stop6h 04m
Frontier
Deal found 5/10![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/11:50 pm
ORD
- TPA
1 stop20h 49m
Frontier
Mon 6/82:25 pm
TPA
- ORD
1 stop6h 04m
Frontier
Deal found 5/12![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Mon 6/112:04 pm
MDW
- TPA
1 stop5h 47m
Frontier
Tue 6/94:46 pm
TPA
- MDW
1 stop6h 25m
Frontier
Deal found 5/11![Frontier logo]()
$173
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/311:10 am
MDW
- TPA
1 stop3h 45m
Southwest
Tue 6/96:55 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/12![Southwest logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Sat 6/66:55 am
ORD
- TPA
1 stop9h 52m
Frontier
Tue 6/162:25 pm
TPA
- ORD
1 stop6h 25m
Frontier
Deal found 5/11![Frontier logo]()
$167
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 Southwest deal was found by Cheapflights users on 5/11. 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.
Wed 6/178:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Wed 6/249:55 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 5/11![Southwest logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Wed 6/1712:04 pm
MDW
- TPA
1 stop8h 13m
Frontier
Wed 6/244:46 pm
TPA
- MDW
1 stop6h 25m
Frontier
Deal found 5/11![Frontier logo]()
$170
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 May 13, 2026.
Search for one-way flight options from Chicago to Clearwater. Find affordable one-way fares based on user searches. Data last updated May 13, 2026.
This American Airlines deal was found by Cheapflights users on 5/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:19 pm
ORD
- TPA
Nonstop2h 47m
American Airlines
Deal found 5/11![American Airlines logo]()
$85
This Southwest deal was found by Cheapflights users on 5/11. 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.
Wed 7/18:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 5/11![Southwest logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 7/76:00 am
MDW
- TPA
1 stop28h 40m
Frontier
Deal found 5/12![Frontier logo]()
$88
This Super.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/101:29 pm
ORD
- TPA
1 stop6h 48m
Frontier
Deal found 5/13![Frontier logo]()
$89
This Southwest deal was found by Cheapflights users on 5/11. 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.
Wed 6/37:40 am
MDW
- TPA
1 stop3h 50m
Southwest
Deal found 5/11![Southwest logo]()
$90
This Trip.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 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 5/10![Frontier logo]()
$91
This Trip.com deal was found by Cheapflights users on 5/11. 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.
Thu 5/281:50 pm
ORD
- TPA
1 stop6h 37m
Frontier
Deal found 5/11![Frontier logo]()
$92
This Trip.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 5/286:00 am
MDW
- TPA
1 stop11h 51m
Frontier
Deal found 5/12![Frontier logo]()
$92
This Trip.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Fri 5/296:55 am
ORD
- TPA
1 stop10h 56m
Frontier
Deal found 5/12![Frontier logo]()
$93
This Frontier deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/51:50 pm
ORD
- TPA
1 stop6h 26m
Frontier
Deal found 5/13![Frontier logo]()
$95
This Frontier deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:11 pm
MDW
- TPA
1 stop5h 41m
Frontier
Deal found 5/13![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Wed 7/221:50 pm
ORD
- TPA
1 stop6h 26m
Frontier
Deal found 5/11![Frontier logo]()
$96
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 May 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $161 (Kiwi.com) |
One-way from | $85 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $252 |
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 May 13, 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
Quickest round-trip
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Tue 6/23
8:15 pm-11:50 pm
Nonstop2h 35m
Tampa
Wed 6/24
9:55 pm-11:35 pm
Nonstop2h 40m
$169
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Tue 6/16
2:35 pm-10:30 pm
1 stop6h 55m
Tampa
Wed 6/24
9:55 pm-11:35 pm
Nonstop2h 40m
$215
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 8/29
1:27 pm-9:19 pm
1 stop6h 52m
Tampa
Sat 9/5
6:15 am-12:30 pm
1 stop7h 15m
$219
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 7/4
7:35 am-11:10 am
Nonstop2h 35m
Tampa
Sat 7/11
9:20 pm-11:00 pm
Nonstop2h 40m
$241
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Tue 6/2
5:56 pm-9:49 pm
Nonstop2h 53m
Tampa
Sat 6/6
7:42 pm-9:53 pm
Nonstop3h 11m
$244
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Wed 6/24
8:15 pm-11:50 pm
Nonstop2h 35m
Tampa
Sat 6/27
7:50 pm-11:15 pm
1 stop4h 25m
$249
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 5/30
5:55 pm-9:30 pm
Nonstop2h 35m
Tampa
Mon 6/1
3:55 pm-8:35 pm
1 stop5h 40m
$250
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Wed 8/26
7:40 am-2:50 pm
2 stops6h 10m
Tampa
Mon 8/31
11:30 am-2:30 pm
1 stop4h 00m
$251
ChicagoTampa
ORD - TPA
ORDTPA
Chicago O'Hare Intl
Mon 7/6
5:30 am-11:34 am
1 stop5h 04m
Tampa
Wed 7/8
5:15 am-8:35 am
1 stop4h 20m
$254
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 6/20
7:45 am-11:25 am
Nonstop2h 40m
Tampa
Tue 6/23
9:55 pm-11:35 pm
Nonstop2h 40m
$256
Showing 1-10 of 44 resultsSorted by cheapest first
Best time to book a flight from Chicago to Clearwater
Have a flexible travel schedule? Discover the best time to fly to Clearwater from Chicago with our price prediction graph.
ORD-TPA
MDW-TPA
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Clearwater
CHI-CL9
ORD-TPA
MDW-TPA
What is the cheapest time of day to fly from CHI to CL9?
Find hourly flight availability from Chicago to Clearwater. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 13, 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 in the evening, 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 May 9, 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 May 13, 2026.
The most flights from CHI to CL9 are scheduled on a Monday (74 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (55 on average).
How much does it cost to fly round-trip from Chicago to Clearwater?
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 May 13, 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
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Clearwater. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chicago to Clearwater
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Complete your trip
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 May 13, 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 13, 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 May 13, 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% |