$74+ 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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Apr 13 — Apr 201
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 March 14, 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 March 14, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:51 pm
TPA
- ORD
Nonstop3h 07m
Frontier
Sat 5/27:34 pm
ORD
- TPA
Nonstop3h 03m
Frontier
Deal found 3/8![Frontier logo]()
$111
This Frontier deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:30 am
TPA
- ORD
Nonstop3h 13m
Frontier
Sun 5/105:11 am
ORD
- TPA
1 stop12h 22m
Frontier
Deal found 3/9![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Fri 4/174:18 pm
TPA
- ORD
Nonstop3h 02m
Multiple Airlines
Mon 4/205:48 pm
ORD
- TPA
Nonstop3h 02m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Fri 4/179:51 pm
TPA
- ORD
Nonstop3h 07m
Frontier
Sat 4/254:28 pm
ORD
- TPA
1 stop14h 06m
Frontier
Deal found 3/12![Frontier logo]()
$118
This Expedia deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:23 pm
TPA
- ORD
Nonstop3h 03m
Spirit Airlines
Wed 4/17:17 am
ORD
- TPA
1 stop9h 24m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2411:45 am
TPA
- ORD
Nonstop3h 13m
Multiple Airlines
Tue 3/317:17 am
ORD
- TPA
1 stop9h 24m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Thu 4/164:18 pm
TPA
- ORD
Nonstop3h 02m
Multiple Airlines
Sun 4/193:08 pm
ORD
- TPA
Nonstop2h 59m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$121
This CheapOair deal was found by Cheapflights users on 3/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/154:45 pm
TPA
- ORD
Nonstop3h 02m
Multiple Airlines
Mon 4/205:48 pm
ORD
- TPA
Nonstop3h 02m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$123
This Expedia deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:38 am
TPA
- ORD
Nonstop3h 15m
Multiple Airlines
Mon 4/2711:28 am
ORD
- TPA
1 stop4h 29m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:13 pm
TPA
- MDW
1 stop10h 01m
Frontier
Sat 4/257:34 pm
MDW
- TPA
1 stop11h 00m
Frontier
Deal found 3/11![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:04 pm
TPA
- ORD
1 stop15h 51m
Frontier
Wed 5/201:59 pm
ORD
- TPA
1 stop6h 28m
Frontier
Deal found 3/10![Frontier logo]()
$126
This eDestinos deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:50 pm
TPA
- MDW
1 stop24h 41m
Frontier
Wed 4/222:15 pm
MDW
- TPA
1 stop18h 49m
Frontier
Deal found 3/10![Frontier logo]()
$131
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 March 14, 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 March 14, 2026.
This CheapOair deal was found by Cheapflights users on 3/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2410:13 pm
TPA
- ORD
Nonstop3h 14m
Multiple Airlines
Sun 4/268:52 pm
ORD
- TPA
Nonstop2h 37m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$158
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:31 pm
TPA
- ORD
1 stop4h 53m
Spirit Airlines
Sun 4/268:52 pm
ORD
- TPA
Nonstop2h 37m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$165
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/910:08 am
TPA
- ORD
Nonstop3h 16m
Frontier
Sun 4/125:25 am
ORD
- TPA
Nonstop2h 48m
Frontier
Deal found 3/13![Frontier logo]()
$187
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/244:20 pm
TPA
- MDW
Nonstop2h 50m
Southwest
Tue 4/285:55 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 3/9![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 3/12. 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 5/97:10 am
TPA
- ORD
Nonstop3h 05m
United Airlines
Sat 5/96:20 pm
ORD
- TPA
Nonstop2h 57m
United Airlines
Deal found 3/12![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 3/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:10 am
TPA
- ORD
1 stop7h 35m
Delta
Tue 5/55:04 pm
ORD
- TPA
1 stop4h 48m
Delta
Deal found 3/12![Delta logo]()
$217
This CheapOair deal was found by Cheapflights users on 3/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:59 pm
TPA
- ORD
1 stop5h 28m
Spirit Airlines
Sun 5/1010:26 am
ORD
- TPA
Nonstop2h 39m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 4/810:54 pm
TPA
- RFD
1 stop11h 53m
Multiple Airlines
Sun 4/1210:37 am
RFD
- TPA
1 stop6h 04m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$202
This Southwest deal was found by Cheapflights users on 3/12. 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 5/96:55 am
TPA
- MDW
Nonstop2h 45m
Southwest
Sat 5/912:45 pm
MDW
- TPA
1 stop6h 40m
Southwest
Deal found 3/12![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/124:37 pm
TPA
- ORD
1 stop4h 49m
Delta
Sat 5/169:10 am
ORD
- TPA
1 stop6h 44m
Delta
Deal found 3/10![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 3/12. 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 5/99:00 am
TPA
- ORD
Nonstop3h 05m
Southwest
Sat 5/91:55 pm
ORD
- TPA
1 stop5h 10m
Southwest
Deal found 3/12![Southwest logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:31 pm
TPA
- RFD
1 stop14h 16m
Multiple Airlines
Sun 5/1010:37 am
RFD
- TPA
1 stop7h 59m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:53 pm
TPA
- ORD
1 stop6h 06m
Delta
Sat 5/163:00 pm
ORD
- TPA
1 stop5h 57m
Delta
Deal found 3/10![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:00 am
TPA
- MDW
1 stop6h 10m
Southwest
Sat 5/29:30 am
MDW
- TPA
1 stop6h 20m
Southwest
Deal found 3/10![Southwest logo]()
$217
This Expedia deal was found by Cheapflights users on 3/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:25 pm
TPA
- ORD
1 stop6h 26m
Multiple Airlines
Wed 6/176:00 am
ORD
- TPA
1 stop8h 00m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$252
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:15 am
TPA
- MDW
Nonstop2h 50m
Southwest
Wed 4/155:55 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 3/9![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 3/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:49 pm
TPA
- MDW
1 stop4h 20m
Delta
Sun 5/106:23 am
MDW
- TPA
1 stop6h 38m
Delta
Deal found 3/13![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 3/13. 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.
Fri 5/87:00 am
TPA
- MDW
Nonstop2h 50m
Southwest
Mon 5/115:00 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 3/13![Southwest logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 4/253:53 pm
TPA
- RFD
1 stop18h 54m
Multiple Airlines
Mon 4/278:35 pm
RFD
- TPA
2 stops26h 51m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$268
This Southwest deal was found by Cheapflights users on 3/12. 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 5/154:20 pm
TPA
- MDW
Nonstop2h 50m
Southwest
Mon 5/188:30 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 3/12![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 3/12. 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 5/154:20 pm
TPA
- MDW
Nonstop2h 50m
Southwest
Sun 5/178:50 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 3/12![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 3/13. 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.
Fri 4/243:35 pm
TPA
- MDW
1 stop5h 55m
Southwest
Sun 4/268:20 am
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 3/13![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Thu 4/99:41 am
TPA
- RFD
2 stops25h 13m
Multiple Airlines
Thu 4/1610:37 am
RFD
- TPA
1 stop21h 28m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$360
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1010:55 pm
TPA
- ORD
2 stops14h 55m
Southwest
Wed 5/135:55 am
ORD
- TPA
2 stops11h 40m
Southwest
Deal found 3/9![Southwest logo]()
$253
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/17:00 am
TPA
- MDW
Nonstop2h 50m
Southwest
Wed 4/85:55 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 3/9![Southwest logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:54 pm
TPA
- RFD
1 stop14h 06m
Multiple Airlines
Sun 5/3111:27 am
RFD
- TPA
1 stop6h 34m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 3/12. 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 5/85:10 am
TPA
- ORD
1 stop9h 05m
Southwest
Sun 5/102:40 pm
ORD
- TPA
2 stops17h 40m
Southwest
Deal found 3/12![Southwest logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 3/1810:54 pm
TPA
- RFD
1 stop11h 53m
Multiple Airlines
Sun 3/2210:37 am
RFD
- TPA
1 stop19h 42m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Thu 3/199:12 am
TPA
- RFD
2 stops25h 37m
Multiple Airlines
Sun 3/2210:37 am
RFD
- TPA
1 stop19h 42m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$562
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/26:46 pm
TPA
- RFD
2 stops16h 08m
Multiple Airlines
Sun 4/510:37 am
RFD
- TPA
1 stop6h 04m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$564
Last-minute flights from Clearwater to ChicagoDiscover last-minute flight deals from Clearwater to Chicago. Data last updated March 14, 2026 and is based on user searches.
Discover last-minute flight deals from Clearwater to Chicago. Data last updated March 14, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:23 pm
TPA
- ORD
Nonstop3h 03m
Spirit Airlines
Wed 4/17:17 am
ORD
- TPA
1 stop9h 24m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2411:45 am
TPA
- ORD
Nonstop3h 13m
Multiple Airlines
Tue 3/317:17 am
ORD
- TPA
1 stop9h 24m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$120
This CheapOair deal was found by Cheapflights users on 3/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/154:45 pm
TPA
- ORD
Nonstop3h 02m
Multiple Airlines
Mon 4/205:48 pm
ORD
- TPA
Nonstop3h 02m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:44 am
TPA
- ORD
1 stop9h 16m
Frontier
Sun 4/193:08 pm
ORD
- TPA
Nonstop2h 59m
Frontier
Deal found 3/11![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:44 am
TPA
- ORD
1 stop9h 16m
Frontier
Sat 4/184:28 pm
ORD
- TPA
1 stop6h 58m
Frontier
Deal found 3/10![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Thu 4/164:18 pm
TPA
- ORD
Nonstop3h 02m
Multiple Airlines
Sun 4/193:08 pm
ORD
- TPA
Nonstop2h 59m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Fri 4/174:18 pm
TPA
- ORD
Nonstop3h 02m
Multiple Airlines
Mon 4/205:48 pm
ORD
- TPA
Nonstop3h 02m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Fri 4/179:51 pm
TPA
- ORD
Nonstop3h 07m
Frontier
Sat 4/254:28 pm
ORD
- TPA
1 stop14h 06m
Frontier
Deal found 3/12![Frontier logo]()
$118
This Super.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:30 am
TPA
- ORD
Nonstop3h 07m
Frontier
Sat 4/257:59 pm
ORD
- TPA
Nonstop3h 00m
Frontier
Deal found 3/11![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:13 pm
TPA
- MDW
1 stop10h 01m
Frontier
Sat 4/257:34 pm
MDW
- TPA
1 stop11h 00m
Frontier
Deal found 3/11![Frontier logo]()
$126
This Expedia deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:38 am
TPA
- ORD
Nonstop3h 15m
Multiple Airlines
Mon 4/2711:28 am
ORD
- TPA
1 stop4h 29m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$125
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:18 pm
TPA
- ORD
Nonstop3h 02m
Spirit Airlines
Sun 4/268:52 pm
ORD
- TPA
Nonstop2h 37m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$127
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 March 14, 2026.
Search for one-way flight options from Clearwater to Chicago. Find affordable one-way fares based on user searches. Data last updated March 14, 2026.
This Trip.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:44 am
TPA
- MDW
1 stop11h 47m
Frontier
Deal found 3/9![Frontier logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:50 pm
TPA
- ORD
1 stop15h 33m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$74
This Cheapflightsfares deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1410:54 pm
TPA
- ORD
1 stop11h 42m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$75
This Trip.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/185:30 am
TPA
- ORD
1 stop6h 14m
Frontier
Deal found 3/9![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/315:30 am
TPA
- MDW
1 stop16h 24m
Frontier
Deal found 3/10![Frontier logo]()
$77
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Sun 5/37:50 pm
TPA
- ORD
1 stop27h 49m
Frontier
Deal found 3/13![Frontier logo]()
$77
This Super.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:30 am
TPA
- ORD
Nonstop3h 07m
Frontier
Deal found 3/9![Frontier logo]()
$78
This Super.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/212:58 pm
TPA
- MDW
1 stop6h 39m
Frontier
Deal found 3/9![Frontier logo]()
$79
This Cheapflightsfares deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/74:54 pm
TPA
- ORD
Nonstop3h 20m
Frontier
Deal found 3/9![Frontier logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Fri 4/176:02 pm
TPA
- MDW
1 stop29h 12m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Sat 4/185:01 am
TPA
- ORD
1 stop17h 11m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$80
This Super.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/234:23 pm
TPA
- ORD
Nonstop3h 03m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$81
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 March 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $111 (Cheapflightsfares) |
One-way from | $74 (Trip.com) |
Popular in | March |
Cheapest in | October |
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 2,558,603 searches. Data last updated March 14, 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 - ORD
TPAORD
Tampa
Fri 4/24
10:13 pm-12:27 am
Nonstop3h 14m
Chicago O'Hare Intl
Sun 4/26
8:52 pm-12:29 am
Nonstop2h 37m
$158
TampaChicago
TPA - ORD
TPAORD
Tampa
Fri 4/24
8:31 pm-12:24 am
1 stop4h 53m
Chicago O'Hare Intl
Sun 4/26
8:52 pm-12:29 am
Nonstop2h 37m
$165
TampaChicago
TPA - ORD
TPAORD
Tampa
Fri 5/8
7:59 pm-12:27 am
1 stop5h 28m
Chicago O'Hare Intl
Sun 5/10
10:26 am-2:05 pm
Nonstop2h 39m
$166
TampaChicago
TPA - ORD
TPAORD
Tampa
Thu 4/9
10:08 am-12:24 pm
Nonstop3h 16m
Chicago O'Hare Intl
Sun 4/12
5:25 am-9:13 am
Nonstop2h 48m
$187
Quickest round-trip
TampaChicago
TPA - MDW
TPAMDW
Tampa
Fri 4/24
4:20 pm-6:10 pm
Nonstop2h 50m
Chicago Midway
Tue 4/28
5:55 am-9:25 am
Nonstop2h 30m
$197
TampaChicago
TPA - ORD
TPAORD
Tampa
Sat 5/9
7:10 am-9:15 am
Nonstop3h 05m
Chicago O'Hare Intl
Sat 5/9
6:20 pm-10:17 pm
Nonstop2h 57m
$197
TampaChicago
TPA - RFD
TPARFD
Tampa
Wed 4/8
10:54 pm-9:47 am
1 stop11h 53m
Chicago Greater Rockford
Sun 4/12
10:37 am-5:41 pm
1 stop6h 04m
$202
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 5/9
6:55 am-8:40 am
Nonstop2h 45m
Chicago Midway
Sat 5/9
12:45 pm-8:25 pm
1 stop6h 40m
$207
TampaChicago
TPA - ORD
TPAORD
Tampa
Sat 5/9
9:00 am-11:05 am
Nonstop3h 05m
Chicago O'Hare Intl
Sat 5/9
1:55 pm-8:05 pm
1 stop5h 10m
$207
TampaChicago
TPA - ORD
TPAORD
Tampa
Tue 5/5
6:10 am-12:45 pm
1 stop7h 35m
Chicago O'Hare Intl
Tue 5/5
5:04 pm-10:52 pm
1 stop4h 48m
$217
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-MDW
TPA-ORD
TPA-RFD
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-MDW
TPA-ORD
TPA-RFD
How far ahead should I book a flight from Clearwater to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Clearwater to Chicago. Price data was last updated on March 6, 2026.
To ensure you get the cheapest price possible for a flight from Clearwater to Chicago, you should look to book at least 77 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Clearwater to Chicago?
Currently, September is the cheapest month in which you can book a flight from Clearwater to Chicago (average of $46). Flying from Clearwater to Chicago in June is currently the most expensive (average of $105). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from 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 March 14, 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 18% versus a flight at noon.
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 March 12, 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.
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 March 14, 2026.
The most flights from CL9 to CHI are scheduled on a Saturday (88 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (40 on average).
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 March 14, 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
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreAnonymous,Feb 2025
MCO - STL
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for 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 March 14, 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 March 14, 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 8 airlines flying from Clearwater to Chicago
Discover the top 8 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 March 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$46 | Average$164 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$60 | Average$177 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$68 | Average$154 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$98 | Average$383 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$328 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$148 | Average$302 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$153 | Average$346 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$306 | FlexibilityNo cancel fee | On-time71% |