$89+ Cheap flights from Clearwater, FL to Chicago (CHI)
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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Jul 16 — Jul 231
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 October or January, booked 83 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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Best
Last-minute
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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 June 16, 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 June 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/228:57 pm
TPA
- RFD
1 stop14h 40m
Multiple Airlines
Sun 8/211:27 am
RFD
- TPA
1 stop18h 56m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
Wed 8/129:35 pm
TPA
- ORD
1 stop26h 52m
Frontier
Tue 8/186:55 am
ORD
- TPA
1 stop10h 56m
Frontier
Deal found 6/10![Frontier logo]()
$208
This Southwest deal was found by Cheapflights users on 6/11. 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 7/219:55 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Tue 7/285:25 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 6/11![Southwest logo]()
$209
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/226:44 am
TPA
- ORD
Nonstop3h 05m
American Airlines
Wed 7/228:29 pm
ORD
- TPA
Nonstop2h 50m
American Airlines
Deal found 6/11![American Airlines logo]()
$209
This Travelocity deal was found by Cheapflights users on 6/11. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/47:00 am
TPA
- MDW
1 stop5h 07m
Frontier
Wed 11/1812:03 pm
MDW
- TPA
1 stop9h 54m
Frontier
Deal found 6/11![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 6/10. 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.
Tue 8/1110:27 am
TPA
- ORD
1 stop6h 33m
Frontier
Wed 8/129:57 pm
ORD
- TPA
1 stop12h 38m
Frontier
Deal found 6/10![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 10/291:05 pm
TPA
- ORD
Nonstop3h 21m
Frontier
Wed 11/42:03 pm
ORD
- TPA
1 stop7h 54m
Frontier
Deal found 6/15![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 8/42:25 pm
TPA
- ORD
1 stop6h 28m
Frontier
Mon 8/107:05 am
ORD
- TPA
1 stop27h 35m
Frontier
Deal found 6/12![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/158:57 pm
TPA
- RFD
1 stop14h 40m
Multiple Airlines
Sun 7/1911:27 am
RFD
- TPA
1 stop18h 56m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 9/157:00 am
TPA
- MDW
1 stop4h 58m
Frontier
Sat 9/197:25 am
MDW
- TPA
1 stop8h 53m
Frontier
Deal found 6/15![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 9/157:00 am
TPA
- ORD
1 stop6h 02m
Frontier
Sat 9/192:03 pm
ORD
- TPA
1 stop7h 54m
Frontier
Deal found 6/15![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/158:57 pm
TPA
- RFD
1 stop14h 40m
Multiple Airlines
Thu 7/2311:27 am
RFD
- TPA
1 stop18h 56m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$215
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 June 16, 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 June 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/228:57 pm
TPA
- RFD
1 stop14h 40m
Multiple Airlines
Sun 8/211:27 am
RFD
- TPA
1 stop18h 56m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 6/10. 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 8/53:40 pm
TPA
- MDW
1 stop5h 30m
Southwest
Wed 8/127:40 am
MDW
- TPA
2 stops6h 10m
Southwest
Deal found 6/10![Southwest logo]()
$246
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:30 am
TPA
- ORD
Nonstop3h 03m
United Airlines
Tue 8/188:45 am
ORD
- TPA
1 stop5h 43m
United Airlines
Deal found 6/10![United Airlines logo]()
$251
This KAYAK deal was found by Cheapflights users on 6/11. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/206:44 am
TPA
- ORD
Nonstop3h 05m
American Airlines
Wed 7/228:29 pm
ORD
- TPA
Nonstop2h 50m
American Airlines
Deal found 6/11![American Airlines logo]()
$332
This JetBlue deal was found by Cheapflights users on 6/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/115:36 pm
TPA
- ORD
1 stop7h 08m
JetBlue
Sat 7/182:35 pm
ORD
- TPA
1 stop5h 22m
JetBlue
Deal found 6/12![JetBlue logo]()
$398
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/298:57 pm
TPA
- RFD
1 stop14h 40m
Multiple Airlines
Sun 8/211:27 am
RFD
- TPA
1 stop18h 56m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:57 pm
TPA
- RFD
1 stop14h 50m
Multiple Airlines
Sun 8/911:37 am
RFD
- TPA
1 stop18h 46m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$221
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/119:00 am
TPA
- ORD
1 stop6h 30m
United Airlines
Sat 8/157:15 am
ORD
- TPA
Nonstop2h 56m
United Airlines
Deal found 6/11![United Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/258:57 pm
TPA
- RFD
1 stop14h 40m
Multiple Airlines
Sun 8/211:27 am
RFD
- TPA
1 stop18h 56m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$226
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:30 am
TPA
- ORD
Nonstop3h 03m
United Airlines
Sat 8/224:20 pm
ORD
- TPA
Nonstop2h 56m
United Airlines
Deal found 6/11![United Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 11/410:49 pm
TPA
- RFD
1 stop10h 51m
Multiple Airlines
Thu 11/129:30 am
RFD
- TPA
1 stop5h 57m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 7/88:57 pm
TPA
- RFD
1 stop14h 40m
Multiple Airlines
Sun 7/1211:27 am
RFD
- TPA
1 stop18h 56m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 6/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:35 pm
TPA
- MDW
Nonstop2h 35m
Southwest
Wed 8/57:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 6/13![Southwest logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/18:57 pm
TPA
- RFD
1 stop14h 40m
Multiple Airlines
Thu 8/1311:37 am
RFD
- TPA
1 stop18h 46m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$235
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/259:20 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Mon 7/272:25 pm
MDW
- TPA
Nonstop2h 40m
Southwest
Deal found 6/15![Southwest logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 7/228:57 pm
TPA
- RFD
1 stop14h 40m
Multiple Airlines
Sun 7/2611:27 am
RFD
- TPA
1 stop18h 56m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$245
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 9/37:30 am
TPA
- ORD
Nonstop3h 03m
United Airlines
Tue 9/85:45 pm
ORD
- TPA
Nonstop2h 56m
United Airlines
Deal found 6/14![United Airlines logo]()
$361
This Southwest deal was found by Cheapflights users on 6/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/47:35 am
TPA
- MDW
Nonstop2h 40m
Southwest
Thu 8/1312:20 pm
MDW
- TPA
1 stop3h 50m
Southwest
Deal found 6/13![Southwest logo]()
$367
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 8/64:30 pm
TPA
- ORD
Nonstop3h 10m
United Airlines
Tue 8/1111:00 am
ORD
- TPA
Nonstop2h 57m
United Airlines
Deal found 6/14![United Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:57 pm
TPA
- RFD
1 stop14h 50m
Multiple Airlines
Sun 8/1611:37 am
RFD
- TPA
2 stops23h 03m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 6/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/78:25 am
TPA
- MDW
Nonstop2h 40m
Southwest
Thu 9/1712:10 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 6/13![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 6/11. 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.
Fri 7/318:00 am
TPA
- MDW
Nonstop2h 40m
Southwest
Mon 8/35:00 am
MDW
- TPA
Nonstop2h 25m
Southwest
Deal found 6/11![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 6/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:23 pm
TPA
- ORD
Nonstop3h 08m
United Airlines
Mon 9/77:15 am
ORD
- TPA
Nonstop2h 56m
United Airlines
Deal found 6/13![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 6/12. 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.
Fri 8/2111:30 am
TPA
- MDW
1 stop4h 00m
Southwest
Sun 8/236:50 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 6/12![Southwest logo]()
$379
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/279:00 am
TPA
- ORD
1 stop6h 27m
United Airlines
Sun 8/305:45 pm
ORD
- TPA
Nonstop2h 56m
United Airlines
Deal found 6/15![United Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/88:57 pm
TPA
- RFD
1 stop14h 40m
Multiple Airlines
Mon 7/137:50 pm
RFD
- TPA
2 stops14h 50m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$292
This United Airlines deal was found by Cheapflights users on 6/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/84:30 pm
TPA
- ORD
Nonstop3h 10m
United Airlines
Tue 7/148:40 am
ORD
- TPA
1 stop5h 45m
United Airlines
Deal found 6/13![United Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/223:25 pm
TPA
- MDW
1 stop5h 40m
Southwest
Wed 7/291:15 pm
MDW
- TPA
2 stops7h 00m
Southwest
Deal found 6/15![Southwest logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/228:57 pm
TPA
- RFD
1 stop14h 40m
Multiple Airlines
Wed 8/511:29 am
RFD
- TPA
2 stops28h 49m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$310
This United Airlines deal was found by Cheapflights users on 6/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/712:30 pm
TPA
- ORD
Nonstop3h 10m
United Airlines
Tue 7/218:40 am
ORD
- TPA
1 stop5h 45m
United Airlines
Deal found 6/13![United Airlines logo]()
$380
Last-minute flights from Clearwater to ChicagoDiscover last-minute flight deals from Clearwater to Chicago. Data last updated June 16, 2026 and is based on user searches.
Discover last-minute flight deals from Clearwater to Chicago. Data last updated June 16, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/11. 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 7/811:55 am
TPA
- MDW
1 stop6h 10m
Southwest
Tue 7/145:25 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 6/11![Southwest logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/1310:31 pm
TPA
- ORD
1 stop14h 44m
Multiple Airlines
Tue 7/218:05 am
ORD
- TPA
1 stop22h 03m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/158:57 pm
TPA
- RFD
1 stop14h 40m
Multiple Airlines
Sun 7/1911:27 am
RFD
- TPA
1 stop18h 56m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/158:57 pm
TPA
- RFD
1 stop14h 40m
Multiple Airlines
Thu 7/2311:27 am
RFD
- TPA
1 stop18h 56m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$215
This Southwest deal was found by Cheapflights users on 6/11. 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 7/219:55 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Tue 7/285:25 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 6/11![Southwest logo]()
$209
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:25 pm
TPA
- ORD
1 stop6h 50m
United Airlines
Tue 7/285:56 pm
ORD
- TPA
Nonstop2h 53m
United Airlines
Deal found 6/11![United Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/228:57 pm
TPA
- RFD
1 stop14h 40m
Multiple Airlines
Sun 8/211:27 am
RFD
- TPA
1 stop18h 56m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$207
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/226:44 am
TPA
- ORD
Nonstop3h 05m
American Airlines
Wed 7/228:29 pm
ORD
- TPA
Nonstop2h 50m
American Airlines
Deal found 6/11![American Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 6/11. 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 7/286:55 am
TPA
- MDW
Nonstop2h 40m
Southwest
Tue 8/116:05 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 6/11![Southwest logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/282:25 pm
TPA
- ORD
1 stop6h 28m
Frontier
Tue 8/41:50 pm
ORD
- TPA
1 stop6h 26m
Frontier
Deal found 6/15![Frontier logo]()
$217
This Cheapflightsfares deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/292:25 pm
TPA
- ORD
1 stop6h 28m
Frontier
Tue 8/41:50 pm
ORD
- TPA
1 stop6h 26m
Frontier
Deal found 6/11![Frontier logo]()
$218
This Expedia deal was found by Cheapflights users on 6/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/292:25 pm
TPA
- MDW
1 stop8h 38m
Frontier
Tue 8/412:11 pm
MDW
- TPA
1 stop8h 05m
Frontier
Deal found 6/11![Frontier logo]()
$220
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 June 16, 2026.
Search for one-way flight options from Clearwater to Chicago. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 8/1110:27 am
TPA
- ORD
1 stop10h 48m
Frontier
Deal found 6/12![Frontier logo]()
$89
This Trip.com deal was found by Cheapflights users on 6/11. 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.
Tue 9/82:25 pm
TPA
- MDW
1 stop8h 46m
Frontier
Deal found 6/11![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 9/912:54 pm
TPA
- MDW
1 stop10h 04m
Frontier
Deal found 6/11![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 8/44:46 pm
TPA
- MDW
1 stop18h 05m
Frontier
Deal found 6/10![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 8/57:00 am
TPA
- ORD
1 stop13h 53m
Frontier
Deal found 6/11![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 7/222:59 pm
TPA
- RFD
1 stop20h 38m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$104
This Super.com deal was found by Cheapflights users on 6/13. 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.
Tue 8/1110:27 am
TPA
- MDW
1 stop7h 24m
Frontier
Deal found 6/13![Frontier logo]()
$104
This Frontier deal was found by Cheapflights users on 6/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:27 am
TPA
- MDW
1 stop6h 23m
Frontier
Deal found 6/12![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 6/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/810:37 am
TPA
- ORD
1 stop6h 33m
Frontier
Deal found 6/12![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/310:31 pm
TPA
- ORD
1 stop14h 44m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$107
This Trip.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/510:27 am
TPA
- MDW
1 stop6h 23m
Frontier
Deal found 6/15![Frontier logo]()
$108
This Trip.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:10 pm
TPA
- ORD
1 stop6h 43m
Frontier
Deal found 6/15![Frontier logo]()
$108
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 June 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $207 (Kiwi.com) |
One-way from | $89 (Kiwi.com) |
Popular in | June |
Cheapest in | October |
Average price | $311 |
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 2,558,603 searches. Data last updated June 16, 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 - RFD
TPARFD
Tampa
Wed 7/22
8:57 pm-10:37 am
1 stop14h 40m
Chicago Greater Rockford
Sun 8/2
11:27 am-7:23 am
1 stop18h 56m
$207
TampaChicago
TPA - RFD
TPARFD
Tampa
Wed 7/29
8:57 pm-10:37 am
1 stop14h 40m
Chicago Greater Rockford
Sun 8/2
11:27 am-7:23 am
1 stop18h 56m
$214
TampaChicago
TPA - RFD
TPARFD
Tampa
Wed 8/5
8:57 pm-10:47 am
1 stop14h 50m
Chicago Greater Rockford
Sun 8/9
11:37 am-7:23 am
1 stop18h 46m
$221
TampaChicago
TPA - RFD
TPARFD
Tampa
Sat 7/25
8:57 pm-10:37 am
1 stop14h 40m
Chicago Greater Rockford
Sun 8/2
11:27 am-7:23 am
1 stop18h 56m
$226
TampaChicago
TPA - RFD
TPARFD
Tampa
Wed 11/4
10:49 pm-8:40 am
1 stop10h 51m
Chicago Greater Rockford
Thu 11/12
9:30 am-4:27 pm
1 stop5h 57m
$226
TampaChicago
TPA - RFD
TPARFD
Tampa
Wed 7/8
8:57 pm-10:37 am
1 stop14h 40m
Chicago Greater Rockford
Sun 7/12
11:27 am-7:23 am
1 stop18h 56m
$227
TampaChicago
TPA - RFD
TPARFD
Tampa
Sat 8/1
8:57 pm-10:37 am
1 stop14h 40m
Chicago Greater Rockford
Thu 8/13
11:37 am-7:23 am
1 stop18h 46m
$235
TampaChicago
TPA - RFD
TPARFD
Tampa
Wed 7/22
8:57 pm-10:37 am
1 stop14h 40m
Chicago Greater Rockford
Sun 7/26
11:27 am-7:23 am
1 stop18h 56m
$245
TampaChicago
TPA - MDW
TPAMDW
Tampa
Wed 8/5
3:40 pm-8:10 pm
1 stop5h 30m
Chicago Midway
Wed 8/12
7:40 am-2:50 pm
2 stops6h 10m
$246
TampaChicago
TPA - RFD
TPARFD
Tampa
Wed 8/12
8:57 pm-10:47 am
1 stop14h 50m
Chicago Greater Rockford
Sun 8/16
11:37 am-11:40 am
2 stops23h 03m
$247
Showing 1-10 of 60 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 June 16, 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 19% 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 June 16, 2026.
The most flights from CL9 to CHI are scheduled on a Saturday (84 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (56 on average).
How much does it cost to fly round-trip from Clearwater to Chicago?
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 June 13, 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. Tuesday at noon 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 June 16, 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.
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
Lansing
Merrillville
Hammond
Porter
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Alternative routes for Clearwater to Chicago
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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 June 16, 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 June 16, 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 2,558,603 searches. Data last updated June 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$46 | Average$167 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$70 | Average$191 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$142 | Average$594 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$324 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$317 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$316 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$362 | FlexibilityNo cancel fee | On-time69% |