$116+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Sep 2 — Sep 91
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
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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 August 3, 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 August 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/192:25 pm
TPA
- ORD
1 stop6h 43m
Frontier
Wed 8/261:59 pm
ORD
- TPA
1 stop9h 36m
Frontier
Deal found 8/2![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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.
Fri 8/282:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Fri 9/411:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Deal found 8/2![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/32:25 pm
TPA
- ORD
1 stop6h 39m
Frontier
Wed 9/96:30 am
ORD
- TPA
1 stop9h 23m
Frontier
Deal found 8/2![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:10 pm
TPA
- MDW
1 stop8h 53m
Frontier
Sat 8/2211:45 am
MDW
- TPA
1 stop6h 04m
Frontier
Deal found 7/31![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:25 pm
TPA
- ORD
1 stop6h 43m
Frontier
Tue 8/251:59 pm
ORD
- TPA
1 stop9h 36m
Frontier
Deal found 7/31![Frontier logo]()
$212
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Tue 8/2511:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Deal found 7/31![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/292:25 pm
TPA
- ORD
1 stop6h 43m
Frontier
Tue 9/17:44 pm
ORD
- TPA
2 stops14h 56m
Frontier
Deal found 8/2![Frontier logo]()
$213
This Trip.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:11 am
TPA
- MDW
1 stop4h 47m
Frontier
Sat 10/2412:03 pm
MDW
- TPA
1 stop9h 56m
Frontier
Deal found 8/1![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:31 pm
TPA
- ORD
2 stops22h 37m
Multiple Airlines
Tue 9/87:05 am
ORD
- TPA
1 stop10h 44m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$214
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:30 am
TPA
- MDW
1 stop4h 00m
Southwest
Mon 8/247:55 pm
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 7/30![Southwest logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/252:25 pm
TPA
- ORD
1 stop6h 34m
Frontier
Thu 8/279:10 pm
ORD
- TPA
2 stops26h 25m
Frontier
Deal found 8/3![Frontier logo]()
$215
This Super.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 pm
TPA
- MDW
1 stop6h 44m
Frontier
Sun 9/276:25 am
MDW
- TPA
1 stop10h 00m
Frontier
Deal found 7/31![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 August 3, 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 August 3, 2026.
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:15 am
TPA
- MDW
Nonstop2h 40m
Southwest
Mon 9/2812:20 pm
MDW
- TPA
1 stop3h 50m
Southwest
Deal found 7/29![Southwest logo]()
$215
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:23 pm
TPA
- ORD
Nonstop3h 08m
United Airlines
Tue 9/84:40 pm
ORD
- TPA
Nonstop2h 56m
United Airlines
Deal found 7/31![United Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 10/306:00 am
TPA
- ORD
1 stop7h 59m
Delta
Mon 11/26:30 am
ORD
- TPA
1 stop6h 29m
Delta
Deal found 8/3![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:30 am
TPA
- MDW
1 stop4h 00m
Southwest
Sat 9/56:00 am
MDW
- TPA
1 stop7h 15m
Southwest
Deal found 7/29![Southwest logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:55 pm
TPA
- RFD
2 stops24h 41m
Multiple Airlines
Sun 8/1611:37 am
RFD
- TPA
1 stop18h 46m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$454
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/111:22 pm
TPA
- ORD
Nonstop3h 08m
United Airlines
Mon 9/148:42 am
ORD
- TPA
1 stop5h 46m
United Airlines
Deal found 7/29![United Airlines logo]()
$230
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:20 pm
TPA
- MDW
1 stop4h 00m
Southwest
Tue 10/61:35 pm
MDW
- TPA
2 stops6h 20m
Southwest
Deal found 7/30![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:48 pm
TPA
- ORD
1 stop7h 11m
Delta
Tue 9/298:05 am
ORD
- TPA
1 stop4h 57m
Delta
Deal found 8/3![Delta logo]()
$255
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/17:00 am
TPA
- ORD
1 stop6h 25m
United Airlines
Sat 9/54:30 pm
ORD
- TPA
Nonstop2h 56m
United Airlines
Deal found 8/3![United Airlines logo]()
$232
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:10 pm
TPA
- MDW
1 stop4h 10m
Southwest
Tue 9/87:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 7/31![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/184:20 pm
TPA
- MDW
1 stop7h 36m
Delta
Sat 11/216:00 am
MDW
- TPA
1 stop7h 15m
Delta
Deal found 8/1![Delta logo]()
$273
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Mon 11/26:50 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 8/1![Southwest logo]()
$235
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:23 pm
TPA
- ORD
1 stop8h 36m
United Airlines
Sun 9/64:30 pm
ORD
- TPA
Nonstop2h 56m
United Airlines
Deal found 7/31![United Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/2912:30 pm
TPA
- MDW
1 stop5h 30m
Southwest
Tue 9/17:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 8/2![Southwest logo]()
$241
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/184:23 pm
TPA
- ORD
Nonstop3h 08m
United Airlines
Sun 9/207:15 am
ORD
- TPA
Nonstop2h 52m
United Airlines
Deal found 7/31![United Airlines logo]()
$271
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:25 am
TPA
- MDW
1 stop6h 25m
Southwest
Mon 9/2812:10 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 7/31![Southwest logo]()
$245
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:26 am
TPA
- ORD
Nonstop3h 06m
United Airlines
Thu 10/88:50 am
ORD
- TPA
1 stop5h 26m
United Airlines
Deal found 7/30![United Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:35 am
TPA
- MDW
1 stop6h 15m
Southwest
Fri 9/47:55 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 8/1![Southwest logo]()
$263
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 7/29![United Airlines logo]()
$295
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:35 pm
TPA
- ORD
Nonstop3h 05m
United Airlines
Sat 10/311:55 pm
ORD
- TPA
Nonstop2h 51m
United Airlines
Deal found 7/31![United Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/68:35 pm
TPA
- RFD
1 stop16h 17m
Multiple Airlines
Sun 1/1012:42 pm
RFD
- TPA
1 stop15h 28m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$600
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:00 am
TPA
- ORD
1 stop6h 27m
United Airlines
Sun 8/304:30 pm
ORD
- TPA
Nonstop2h 56m
United Airlines
Deal found 8/1![United Airlines logo]()
$335
Last-minute flights from Clearwater to ChicagoDiscover last-minute flight deals from Clearwater to Chicago. Data last updated August 3, 2026 and is based on user searches.
Discover last-minute flight deals from Clearwater to Chicago. Data last updated August 3, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:10 pm
TPA
- MDW
1 stop8h 53m
Frontier
Sat 8/2211:45 am
MDW
- TPA
1 stop6h 04m
Frontier
Deal found 7/31![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:40 pm
TPA
- ORD
1 stop15h 13m
Frontier
Fri 9/2510:26 am
ORD
- TPA
1 stop11h 08m
Frontier
Deal found 7/31![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/182:25 pm
TPA
- ORD
1 stop6h 43m
Frontier
Fri 8/287:05 am
ORD
- TPA
1 stop10h 44m
Frontier
Deal found 8/2![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/192:25 pm
TPA
- ORD
1 stop6h 43m
Frontier
Wed 8/261:59 pm
ORD
- TPA
1 stop9h 36m
Frontier
Deal found 8/2![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:25 pm
TPA
- ORD
1 stop6h 43m
Frontier
Sat 8/221:59 pm
ORD
- TPA
1 stop9h 36m
Frontier
Deal found 7/31![Frontier logo]()
$212
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:30 am
TPA
- MDW
1 stop4h 00m
Southwest
Mon 8/247:55 pm
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 7/30![Southwest logo]()
$215
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Tue 8/2511:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Deal found 7/31![Frontier logo]()
$213
This Frontier deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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.
Fri 8/282:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Fri 9/411:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Deal found 8/2![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/292:25 pm
TPA
- ORD
1 stop6h 43m
Frontier
Tue 9/17:44 pm
ORD
- TPA
2 stops22h 05m
Frontier
Deal found 8/3![Frontier logo]()
$213
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/294:23 pm
TPA
- ORD
Nonstop3h 08m
United Airlines
Mon 8/318:45 am
ORD
- TPA
1 stop5h 43m
United Airlines
Deal found 7/29![United Airlines logo]()
$215
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:15 am
TPA
- MDW
Nonstop2h 40m
Southwest
Mon 9/146:20 pm
MDW
- TPA
Nonstop2h 40m
Southwest
Deal found 7/29![Southwest logo]()
$214
This Super.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 pm
TPA
- MDW
1 stop6h 44m
Frontier
Sun 9/276:25 am
MDW
- TPA
1 stop10h 00m
Frontier
Deal found 7/31![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 August 3, 2026.
Search for one-way flight options from Clearwater to Chicago. Find affordable one-way fares based on user searches. Data last updated August 3, 2026.
This Trip.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:25 pm
TPA
- ORD
1 stop6h 43m
Frontier
Deal found 7/29![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/48:07 pm
TPA
- MDW
1 stop15h 43m
Frontier
Deal found 8/2![Frontier logo]()
$117
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/145:15 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 8/3![Southwest logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 10/276:23 pm
TPA
- RFD
2 stops39h 27m
Multiple Airlines
Deal found 8/2![Multiple Airlines logo]()
$118
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:33 pm
TPA
- ORD
Nonstop3h 05m
United Airlines
Deal found 7/31![United Airlines logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:07 pm
TPA
- MDW
1 stop15h 43m
Frontier
Deal found 7/30![Frontier logo]()
$119
This Cheapflightsfares deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:56 pm
TPA
- ORD
1 stop15h 36m
Frontier
Deal found 7/31![Frontier logo]()
$119
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:20 am
TPA
- MDW
2 stops7h 45m
Southwest
Deal found 7/30![Southwest logo]()
$120
This Trip.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:05 am
TPA
- ORD
1 stop14h 03m
Frontier
Deal found 8/1![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:40 pm
TPA
- ORD
1 stop15h 13m
Frontier
Deal found 8/1![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:05 am
TPA
- MDW
2 stops14h 26m
Frontier
Deal found 7/31![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/302:25 pm
TPA
- ORD
1 stop18h 28m
Frontier
Deal found 7/31![Frontier logo]()
$122
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 August 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $210 (Kiwi.com) |
One-way from | $116 (Trip.com) |
Popular in | July |
Cheapest in | October |
Average price | $241 |
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 August 3, 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 - MDW
TPAMDW
Tampa
Thu 9/24
5:15 am-6:55 am
Nonstop2h 40m
Chicago Midway
Mon 9/28
12:20 pm-5:10 pm
1 stop3h 50m
$215
TampaChicago
TPA - ORD
TPAORD
Tampa
Sat 9/5
4:23 pm-6:31 pm
Nonstop3h 08m
Chicago O'Hare Intl
Tue 9/8
4:40 pm-8:36 pm
Nonstop2h 56m
$222
TampaChicago
TPA - MDW
TPAMDW
Tampa
Thu 9/3
11:30 am-2:30 pm
1 stop4h 00m
Chicago Midway
Sat 9/5
6:00 am-2:15 pm
1 stop7h 15m
$224
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 10/3
12:20 pm-3:20 pm
1 stop4h 00m
Chicago Midway
Tue 10/6
1:35 pm-8:55 pm
2 stops6h 20m
$228
TampaChicago
TPA - ORD
TPAORD
Tampa
Fri 9/11
1:22 pm-3:30 pm
Nonstop3h 08m
Chicago O'Hare Intl
Mon 9/14
8:42 am-3:28 pm
1 stop5h 46m
$230
TampaChicago
TPA - ORD
TPAORD
Tampa
Tue 9/1
7:00 am-12:25 pm
1 stop6h 25m
Chicago O'Hare Intl
Sat 9/5
4:30 pm-8:26 pm
Nonstop2h 56m
$232
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 9/5
4:10 pm-7:20 pm
1 stop4h 10m
Chicago Midway
Tue 9/8
7:30 am-11:00 am
Nonstop2h 30m
$232
Quickest round-trip
TampaChicago
TPA - MDW
TPAMDW
Tampa
Tue 10/20
6:00 pm-7:40 pm
Nonstop2h 40m
Chicago Midway
Mon 11/2
6:50 pm-10:25 pm
Nonstop2h 35m
$235
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 8/29
12:30 pm-5:00 pm
1 stop5h 30m
Chicago Midway
Tue 9/1
7:30 am-11:00 am
Nonstop2h 30m
$241
TampaChicago
TPA - ORD
TPAORD
Tampa
Fri 10/30
6:00 am-12:59 pm
1 stop7h 59m
Chicago O'Hare Intl
Mon 11/2
6:30 am-1:59 pm
1 stop6h 29m
$242
Showing 1-10 of 52 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-ORD
TPA-MDW
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-ORD
TPA-MDW
TPA-RFD
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 August 3, 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 31% 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 August 3, 2026.
The most flights from CL9 to CHI are scheduled on a Friday (78 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (34 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 $176 and $312 in August.The cheapest round-trip price found within the last 5 days was $210 on Frontier (Aug 19-Aug 27).
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 August 1, 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 August 3, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andJetBlue 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.
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
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
Lansing
Merrillville
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 August 3, 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 August 3, 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 August 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$46 | Average$194 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$82 | Average$200 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$98 | Average$370 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$329 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$348 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$327 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$367 | FlexibilityNo cancel fee | On-time69% |