$107+ Cheap flights from Clearwater, FL to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Oct 10 — Oct 171
Round-trip
1 adult, Economy
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Find cheap flights from Clearwater to Chicago 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 Clearwater to Chicago are usually found in January or February, booked 37 days in advance, depart on a Thursday or Friday and return on a Wednesday
Cheap flight deals from Clearwater to Chicago
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Cheapest flights from Clearwater to ChicagoExplore the most affordable flight options available from Clearwater to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
Explore the most affordable flight options available from Clearwater to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
This Super.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2010:39 pm -
Nonstop3h 04m
Sun 11/226:30 am -
Nonstop2h 45m
Deal found 9/6![Frontier logo]()
$210
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:59 pm -
1 stop5h 47m
Tue 10/66:25 am -
1 stop9h 53m
Deal found 9/10![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Fri 10/212:59 pm -
1 stop6h 24m
Mon 10/57:25 am -
2 stops32h 53m
Deal found 9/8![Frontier logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:17 pm -
1 stop8h 18m
Mon 10/510:26 am -
1 stop11h 08m
Deal found 9/10![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Thu 10/112:59 pm -
1 stop5h 47m
Sat 10/36:25 am -
1 stop9h 53m
Deal found 9/8![Frontier logo]()
$213
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/512:54 pm -
1 stop6h 51m
Sun 11/810:26 am -
1 stop5h 56m
Deal found 9/10![Frontier logo]()
$213
This Expedia deal was found by Cheapflights users on 9/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:08 am -
1 stop11h 39m
Tue 11/36:16 am -
1 stop10h 17m
Deal found 9/9![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Mon 9/286:00 pm -
1 stop18h 51m
Wed 9/307:28 pm -
1 stop15h 11m
Deal found 9/9![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Sat 10/246:29 pm -
1 stop6h 14m
Tue 10/276:42 pm -
1 stop16h 07m
Deal found 9/8![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Mon 9/286:00 pm -
1 stop18h 51m
Mon 10/57:28 pm -
1 stop15h 11m
Deal found 9/9![Frontier logo]()
$215
This CheapOair deal was found by Cheapflights users on 9/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:59 pm -
1 stop5h 47m
Mon 10/56:50 am -
1 stop9h 35m
Deal found 9/8![Frontier logo]()
$216
This CheapOair deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:08 am -
1 stop6h 43m
Mon 11/210:26 am -
1 stop11h 09m
Deal found 9/6![Frontier logo]()
$216
Best flights from Clearwater to ChicagoDiscover carefully curated flight deals from Clearwater to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
Discover carefully curated flight deals from Clearwater to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
This Frontier deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:41 pm -
1 stop11h 06m
Mon 11/96:16 am -
1 stop10h 06m
Deal found 9/5![Frontier logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:49 pm -
1 stop11h 01m
Sun 10/189:33 pm -
2 stops37h 12m
Deal found 9/9![Multiple Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:05 pm -
Nonstop2h 40m
Sun 10/256:55 am -
Nonstop2h 30m
Deal found 9/5![Southwest logo]()
$276
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/712:19 pm -
Nonstop3h 03m
Tue 10/138:50 am -
1 stop5h 26m
Deal found 9/9![United Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/66:20 pm -
1 stop4h 50m
Wed 3/101:05 pm -
1 stop5h 08m
Deal found 9/6![Delta logo]()
$301
This Sun Country Air deal was found by Cheapflights users on 9/7. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/268:45 pm -
1 stop23h 25m
Sun 1/37:50 pm -
1 stop13h 50m
Deal found 9/7![Sun Country Air logo]()
$405
This Southwest deal was found by Cheapflights users on 9/8. 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 10/104:25 pm -
Nonstop2h 45m
Wed 10/141:00 pm -
1 stop4h 20m
Deal found 9/8![Southwest logo]()
$282
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:30 pm -
Nonstop3h 05m
Mon 11/98:54 am -
Nonstop2h 58m
Deal found 9/5![United Airlines logo]()
$296
This Southwest deal was found by Cheapflights users on 9/8. 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 12/26:05 pm -
Nonstop2h 40m
Sun 12/612:50 pm -
1 stop3h 55m
Deal found 9/8![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:10 am -
1 stop4h 29m
Wed 10/285:27 am -
1 stop6h 17m
Deal found 9/5![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 9/10. 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.
Fri 11/204:35 pm -
Nonstop2h 45m
Wed 12/210:20 am -
1 stop3h 55m
Deal found 9/10![Southwest logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/610:49 pm -
1 stop12h 06m
Thu 3/1110:45 am -
1 stop19h 25m
Deal found 9/6![Multiple Airlines logo]()
$342
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:33 pm -
Nonstop3h 05m
Sat 10/38:50 am -
1 stop5h 26m
Deal found 9/10![United Airlines logo]()
$312
This Delta deal was found by Cheapflights users on 9/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:20 am -
1 stop4h 51m
Mon 11/96:49 am -
1 stop7h 26m
Deal found 9/8![Delta logo]()
$321
This Southwest deal was found by Cheapflights users on 9/10. 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.
Wed 10/77:20 am -
Nonstop2h 40m
Sat 10/108:10 am -
1 stop7h 40m
Deal found 9/10![Southwest logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1110:49 pm -
1 stop10h 51m
Sun 11/158:37 pm -
2 stops11h 55m
Deal found 9/6![Multiple Airlines logo]()
$350
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Sun 10/117:26 am -
Nonstop3h 06m
Fri 10/164:00 pm -
1 stop6h 32m
Deal found 9/8![United Airlines logo]()
$321
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:05 am -
Nonstop2h 40m
Thu 10/297:05 am -
1 stop3h 55m
Deal found 9/7![Southwest logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:14 pm -
2 stops14h 40m
Sun 10/2510:20 am -
1 stop19h 50m
Deal found 9/6![Multiple Airlines logo]()
$367
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:26 am -
Nonstop3h 06m
Mon 10/512:59 pm -
Nonstop2h 48m
Deal found 9/7![United Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 9/9. 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.
Thu 10/157:10 pm -
1 stop5h 45m
Mon 10/198:35 am -
Nonstop2h 35m
Deal found 9/9![Southwest logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Thu 10/296:14 pm -
2 stops14h 40m
Sun 11/110:20 am -
1 stop19h 50m
Deal found 9/7![Multiple Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:10 pm -
Nonstop2h 45m
Fri 10/3012:45 pm -
1 stop6h 00m
Deal found 9/7![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 9/8. 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 10/39:10 am -
1 stop7h 10m
Tue 10/66:05 pm -
Nonstop2h 40m
Deal found 9/8![Southwest logo]()
$301
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/82:25 pm -
Nonstop3h 09m
Mon 3/157:25 am -
Nonstop2h 41m
Deal found 9/6![United Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/1010:49 pm -
1 stop11h 51m
Sun 10/119:33 pm -
2 stops37h 12m
Deal found 9/10![Multiple Airlines logo]()
$416
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:33 pm -
Nonstop3h 05m
Sun 10/255:00 am -
1 stop8h 07m
Deal found 9/7![United Airlines logo]()
$411
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:05 pm -
2 stops5h 35m
Mon 12/1410:20 am -
1 stop3h 55m
Deal found 9/8![Southwest logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Sat 11/710:49 pm -
1 stop11h 51m
Sun 11/88:37 pm -
2 stops11h 55m
Deal found 9/7![Multiple Airlines logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/610:49 pm -
1 stop12h 06m
Sun 3/1410:45 am -
1 stop19h 25m
Deal found 9/6![Multiple Airlines logo]()
$448
Last-minute flights from Clearwater to ChicagoDiscover last-minute flight deals from Clearwater to Chicago. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Clearwater to Chicago. Data last updated September 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Mon 9/289:22 pm -
1 stop18h 58m
Thu 10/110:26 am -
1 stop5h 59m
Deal found 9/7![Multiple Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Mon 9/286:00 pm -
1 stop18h 51m
Wed 9/307:28 pm -
1 stop15h 11m
Deal found 9/9![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Mon 9/286:00 pm -
1 stop18h 51m
Mon 10/57:28 pm -
1 stop15h 11m
Deal found 9/9![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Wed 9/307:15 am -
1 stop5h 36m
Sat 10/36:20 am -
1 stop9h 58m
Deal found 9/8![Frontier logo]()
$210
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:59 pm -
1 stop5h 47m
Tue 10/66:25 am -
1 stop9h 53m
Deal found 9/10![Frontier logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:17 pm -
1 stop8h 18m
Mon 10/510:26 am -
1 stop11h 08m
Deal found 9/10![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Thu 10/112:59 pm -
1 stop5h 47m
Sat 10/36:25 am -
1 stop9h 53m
Deal found 9/8![Frontier logo]()
$213
This CheapOair deal was found by Cheapflights users on 9/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:59 pm -
1 stop5h 47m
Mon 10/56:50 am -
1 stop9h 35m
Deal found 9/8![Frontier logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Fri 10/212:59 pm -
1 stop6h 24m
Mon 10/57:25 am -
2 stops32h 53m
Deal found 9/8![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Sat 10/246:29 pm -
1 stop6h 14m
Tue 10/276:42 pm -
1 stop16h 07m
Deal found 9/8![Frontier logo]()
$215
This Expedia deal was found by Cheapflights users on 9/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:08 am -
1 stop11h 39m
Tue 11/36:16 am -
1 stop10h 17m
Deal found 9/9![Frontier logo]()
$214
This CheapOair deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:08 am -
1 stop6h 43m
Mon 11/210:26 am -
1 stop11h 09m
Deal found 9/6![Frontier logo]()
$216
One-way flights from Clearwater to ChicagoSearch for one-way flight options from Clearwater to Chicago. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
Search for one-way flight options from Clearwater to Chicago. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:08 am -
1 stop12h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$107
This Super.com deal was found by Cheapflights users on 9/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:57 pm -
1 stop6h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Mon 10/127:59 pm -
1 stop16h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$108
This CheapOair deal was found by Cheapflights users on 9/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/292:03 pm -
1 stop4h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$109
This Cheapflightsfares deal was found by Cheapflights users on 9/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:35 am -
Nonstop3h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/712:52 pm -
1 stop5h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:57 pm -
2 stops15h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$110
This Cheapflightsfares deal was found by Cheapflights users on 9/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:45 pm -
1 stop6h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$110
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/98:01 am -
1 stop5h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$111
This Mytrip deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:29 pm -
1 stop6h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Sun 10/47:15 am -
1 stop27h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$112
This Trip.com deal was found by Cheapflights users on 9/10. 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.
Mon 10/127:08 am -
1 stop17h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$113
Find flight deals from Clearwater to Chicago
Keep the following information in mind while searching for Clearwater to Chicago flight deals. Data was last updated September 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $210 (Super.com) |
One-way from | $107 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $265 |
Cheapflights Fare Finder
Customize your flight search to find flights from Clearwater to Chicago 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 7,457,451 searches. Data last updated September 10, 2026.
Use the filters below to find and compare flights from Clearwater to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
TampaChicago
TPA Tampa - RFD Chicago Greater Rockford
TPARFD
Tampa
Sat 10/3
3:11 pm-9:18 am
1 stop19h 07m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$114
Quickest round-trip
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Sat 10/24
7:35 am-9:15 am
Nonstop2h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$131
TampaChicago
TPA Tampa - ORD Chicago O'Hare Intl
TPAORD
Tampa
Sat 10/31
6:35 pm-8:40 pm
Nonstop3h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$131
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Tue 11/10
1:20 pm-3:00 pm
Nonstop2h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$131
TampaChicago
TPA Tampa - ORD Chicago O'Hare Intl
TPAORD
Tampa
Tue 12/1
6:35 pm-8:40 pm
Nonstop3h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$131
TampaChicago
TPA Tampa - RFD Chicago Greater Rockford
TPARFD
Tampa
Sat 10/31
1:41 pm-10:30 am
2 stops21h 49m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
TampaChicago
TPA Tampa - RFD Chicago Greater Rockford
TPARFD
Tampa
Thu 10/22
12:50 pm-7:54 am
2 stops20h 04m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$136
TampaChicago
TPA Tampa - ORD Chicago O'Hare Intl
TPAORD
Tampa
Tue 12/22
7:45 am-1:04 pm
1 stop6h 19m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$141
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Tue 1/5
9:35 am-12:55 pm
1 stop4h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$141
TampaChicago
TPA Tampa - ORD Chicago O'Hare Intl
TPAORD
Tampa
Tue 10/6
8:30 am-1:47 pm
1 stop6h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
Showing 1-10 of 58 resultsSorted by cheapest first
Best time to book a flight from Clearwater to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Clearwater with our price prediction graph.
TPA-RFD
TPA-MDW
TPA-ORD
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 Clearwater to Chicago
CL9-CHI
TPA-RFD
TPA-MDW
TPA-ORD
What is the cheapest time of day to fly from CL9 to CHI?
Find hourly flight availability from Clearwater to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 10, 2026.
When flying from Clearwater to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 25% versus a flight at noon.
Weekly flight availability from Clearwater to Chicago
Explore weekly flight availability from Clearwater to Chicago. 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 September 10, 2026.
The most flights from CL9 to CHI are scheduled on a Wednesday (64 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (31 on average).
How much does it cost to fly round-trip from Clearwater to Chicago?
Airfare is typical for this route at the moment.
Clearwater to Chicago flights typically cost between $196 and $335 in November.The cheapest round-trip price found within the last 5 days was $210 on Frontier (Nov 20-Nov 22).
What is the cheapest day to fly from Clearwater to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Clearwater to Chicago. Price data was last updated on September 5, 2026.
Travelers seeking maximum savings on their Clearwater to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 10, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Clearwater to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Clearwater to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Clearwater to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 10, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Clearwater to Chicago by cabin class
Find flights from Clearwater to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Clearwater and Chicago flights
Browse other Clearwater and Chicago flight options. Last updated on September 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Clearwater to Chicago flights
Consider these flights traveling from Clearwater to Chicago.
Top 7 airlines flying from Clearwater to Chicago
Discover the top 7 airlines that operate flights from Clearwater to Chicago. 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 7,457,451 searches. Data last updated September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$205 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$82 | Average$199 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$98 | Average$307 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$330 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$355 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$332 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$369 | FlexibilityNo cancel fee | On-time69% |