$73+ 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 6/23. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
mag 29 — giu 51
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 Friday or Thursday and return on a Wednesday
Cheap flight deals from Clearwater to Chicago
Cheapest
Best
Last-minute
One-way
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 aprile 29, 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 aprile 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
mer 5/2710:21 am
TPA
- ORD
Nonstop3h 02m
Multiple Airlines
mar 6/21:50 pm
ORD
- TPA
1 stop6h 37m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
mer 5/274:46 pm
TPA
- MDW
1 stop6h 16m
Frontier
lun 6/112:04 pm
MDW
- TPA
1 stop8h 23m
Frontier
Deal found 4/25![Frontier logo]()
$149
This Booking.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sab 5/161:25 pm
TPA
- ORD
1 stop7h 26m
Multiple Airlines
dom 5/178:30 am
ORD
- TPA
Nonstop2h 39m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
mer 5/274:46 pm
TPA
- MDW
1 stop6h 16m
Frontier
mar 6/212:27 pm
MDW
- TPA
1 stop5h 24m
Frontier
Deal found 4/28![Frontier logo]()
$150
This Frontier deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
ven 5/19:51 pm
TPA
- ORD
Nonstop3h 07m
Frontier
ven 5/86:55 am
ORD
- TPA
1 stop8h 14m
Frontier
Deal found 4/24![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
mer 5/279:46 pm
TPA
- ORD
1 stop15h 51m
Multiple Airlines
sab 5/306:55 am
ORD
- TPA
1 stop9h 52m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
mar 5/262:25 pm
TPA
- MDW
1 stop8h 37m
Frontier
lun 6/112:04 pm
MDW
- TPA
1 stop5h 47m
Frontier
Deal found 4/28![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
ven 5/19:51 pm
TPA
- ORD
Nonstop3h 07m
Multiple Airlines
dom 5/38:52 pm
ORD
- TPA
Nonstop2h 37m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
sab 5/168:17 am
TPA
- MDW
1 stop14h 45m
Frontier
lun 5/186:00 am
MDW
- TPA
1 stop9h 09m
Frontier
Deal found 4/24![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
gio 5/282:25 pm
TPA
- ORD
1 stop18h 30m
Frontier
sab 5/301:50 pm
ORD
- TPA
1 stop5h 08m
Frontier
Deal found 4/28![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
mar 5/262:25 pm
TPA
- ORD
1 stop6h 16m
Frontier
mer 6/31:50 pm
ORD
- TPA
1 stop6h 37m
Frontier
Deal found 4/28![Frontier logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
mer 6/32:25 pm
TPA
- ORD
1 stop6h 26m
Multiple Airlines
mar 6/97:52 am
ORD
- TPA
1 stop22h 38m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$155
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 aprile 29, 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 aprile 29, 2026.
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
mer 5/277:42 pm
TPA
- ORD
Nonstop3h 11m
United Airlines
mar 6/25:56 pm
ORD
- TPA
Nonstop2h 53m
United Airlines
Deal found 4/27![United Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
sab 5/3011:26 am
TPA
- RFD
1 stop24h 11m
Multiple Airlines
gio 6/411:27 am
RFD
- TPA
1 stop8h 24m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$199
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
mar 6/305:15 am
TPA
- MDW
1 stop5h 54m
Delta
sab 7/44:25 pm
MDW
- TPA
1 stop7h 06m
Delta
Deal found 4/25![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
mar 8/115:35 pm
TPA
- MDW
Nonstop2h 35m
Southwest
mar 9/297:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 4/25![Southwest logo]()
$229
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
lun 6/17:27 pm
TPA
- ORD
Nonstop3h 11m
United Airlines
mer 6/38:40 am
ORD
- TPA
1 stop5h 35m
United Airlines
Deal found 4/28![United Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
mer 7/158:28 pm
TPA
- RFD
1 stop15h 09m
Multiple Airlines
dom 7/1911:27 am
RFD
- TPA
1 stop18h 56m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$211
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
mar 6/235:15 am
TPA
- MDW
1 stop5h 54m
Delta
sab 6/271:21 pm
MDW
- TPA
1 stop6h 50m
Delta
Deal found 4/28![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
mar 6/239:55 pm
TPA
- MDW
Nonstop2h 40m
Southwest
mer 7/15:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 4/28![Southwest logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
sab 8/18:28 pm
TPA
- RFD
1 stop15h 09m
Multiple Airlines
gio 8/611:37 am
RFD
- TPA
1 stop8h 42m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$226
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
mar 6/305:15 am
TPA
- MDW
1 stop5h 54m
Delta
dom 7/56:00 am
MDW
- TPA
1 stop7h 15m
Delta
Deal found 4/25![Delta logo]()
$244
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
sab 5/167:15 am
TPA
- MDW
1 stop6h 55m
Southwest
mar 5/194:45 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 4/27![Southwest logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
mer 5/279:46 pm
TPA
- RFD
1 stop13h 51m
Multiple Airlines
lun 6/18:03 pm
RFD
- TPA
2 stops21h 48m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$238
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
ven 7/37:45 pm
TPA
- ORD
Nonstop3h 11m
United Airlines
mer 7/88:40 am
ORD
- TPA
1 stop5h 35m
United Airlines
Deal found 4/28![United Airlines logo]()
$262
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
mer 7/12:00 pm
TPA
- ORD
1 stop7h 31m
Delta
lun 7/66:35 am
ORD
- TPA
1 stop6h 40m
Delta
Deal found 4/25![Delta logo]()
$244
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
mer 5/273:55 pm
TPA
- MDW
Nonstop2h 45m
Southwest
mar 6/24:45 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 4/27![Southwest logo]()
$256
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
gio 9/109:55 am
TPA
- ORD
Nonstop3h 01m
United Airlines
mer 9/1612:57 pm
ORD
- TPA
1 stop6h 26m
United Airlines
Deal found 4/24![United Airlines logo]()
$266
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
lun 5/255:26 am
TPA
- MDW
1 stop5h 34m
Delta
ven 6/55:08 pm
MDW
- TPA
1 stop4h 49m
Delta
Deal found 4/28![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
gio 6/255:20 am
TPA
- MDW
Nonstop2h 40m
Southwest
sab 6/275:50 pm
MDW
- TPA
1 stop4h 40m
Southwest
Deal found 4/26![Southwest logo]()
$266
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
ven 10/212:27 pm
TPA
- ORD
Nonstop2h 57m
United Airlines
dom 10/47:30 am
ORD
- TPA
Nonstop2h 41m
United Airlines
Deal found 4/24![United Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
lun 6/297:46 pm
TPA
- RFD
2 stops38h 27m
Multiple Airlines
dom 7/511:27 am
RFD
- TPA
1 stop18h 56m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
lun 5/255:26 am
TPA
- ORD
1 stop5h 50m
Delta
mer 5/279:49 am
ORD
- TPA
1 stop6h 52m
Delta
Deal found 4/26![Delta logo]()
$258
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
gio 6/1810:30 pm
TPA
- MDW
Nonstop2h 35m
Southwest
ven 6/198:10 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 4/28![Southwest logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
sab 6/2710:28 pm
TPA
- RFD
1 stop13h 09m
Multiple Airlines
ven 7/37:50 pm
RFD
- TPA
2 stops27h 19m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
mer 7/86:20 am
TPA
- ORD
1 stop4h 50m
Delta
mar 7/1411:20 am
ORD
- TPA
1 stop4h 28m
Delta
Deal found 4/28![Delta logo]()
$261
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
ven 7/310:30 pm
TPA
- MDW
Nonstop2h 35m
Southwest
dom 7/59:20 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 4/26![Southwest logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
sab 6/2712:15 pm
TPA
- RFD
2 stops23h 22m
Multiple Airlines
dom 7/511:27 am
RFD
- TPA
1 stop9h 06m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
dom 5/247:56 pm
TPA
- ORD
1 stop5h 12m
Delta
mar 6/29:49 am
ORD
- TPA
1 stop4h 43m
Delta
Deal found 4/28![Delta logo]()
$273
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
gio 5/142:00 pm
TPA
- ORD
Nonstop3h 05m
Southwest
sab 5/2311:50 am
ORD
- TPA
Nonstop2h 40m
Southwest
Deal found 4/27![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
ven 7/37:57 pm
TPA
- ORD
1 stop5h 02m
Delta
lun 7/65:30 am
ORD
- TPA
1 stop5h 04m
Delta
Deal found 4/25![Delta logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
sab 6/278:14 am
TPA
- RFD
1 stop27h 23m
Multiple Airlines
sab 7/410:05 am
RFD
- TPA
2 stops20h 33m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$330
Last-minute flights from Clearwater to ChicagoDiscover last-minute flight deals from Clearwater to Chicago. Data last updated aprile 29, 2026 and is based on user searches.
Discover last-minute flight deals from Clearwater to Chicago. Data last updated aprile 29, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
ven 5/19:51 pm
TPA
- ORD
Nonstop3h 07m
Frontier
ven 5/86:55 am
ORD
- TPA
1 stop8h 14m
Frontier
Deal found 4/24![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
ven 5/19:51 pm
TPA
- ORD
Nonstop3h 07m
Multiple Airlines
dom 5/38:52 pm
ORD
- TPA
Nonstop2h 37m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$152
This Cheapflightsfares deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
ven 5/18:31 pm
TPA
- ORD
1 stop4h 53m
Spirit Airlines
sab 5/25:09 pm
ORD
- TPA
Nonstop2h 39m
Spirit Airlines
Deal found 4/24![Spirit Airlines logo]()
$156
This Booking.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sab 5/161:25 pm
TPA
- ORD
1 stop7h 26m
Multiple Airlines
dom 5/178:30 am
ORD
- TPA
Nonstop2h 39m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
sab 5/168:17 am
TPA
- MDW
1 stop14h 45m
Frontier
lun 5/186:00 am
MDW
- TPA
1 stop9h 09m
Frontier
Deal found 4/24![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
mar 5/262:25 pm
TPA
- MDW
1 stop8h 37m
Frontier
lun 6/112:04 pm
MDW
- TPA
1 stop5h 47m
Frontier
Deal found 4/28![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
mar 5/262:25 pm
TPA
- ORD
1 stop6h 16m
Frontier
mer 6/31:50 pm
ORD
- TPA
1 stop6h 37m
Frontier
Deal found 4/28![Frontier logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
mer 5/2710:21 am
TPA
- ORD
Nonstop3h 02m
Multiple Airlines
mar 6/21:50 pm
ORD
- TPA
1 stop6h 37m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
mer 5/274:46 pm
TPA
- MDW
1 stop6h 16m
Frontier
lun 6/112:04 pm
MDW
- TPA
1 stop8h 23m
Frontier
Deal found 4/25![Frontier logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
mer 5/274:46 pm
TPA
- MDW
1 stop6h 16m
Frontier
mar 6/212:27 pm
MDW
- TPA
1 stop5h 24m
Frontier
Deal found 4/28![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
mer 5/279:46 pm
TPA
- ORD
1 stop15h 51m
Multiple Airlines
sab 5/306:55 am
ORD
- TPA
1 stop9h 52m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
gio 5/282:25 pm
TPA
- ORD
1 stop18h 30m
Frontier
sab 5/301:50 pm
ORD
- TPA
1 stop5h 08m
Frontier
Deal found 4/28![Frontier logo]()
$153
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 aprile 29, 2026.
Search for one-way flight options from Clearwater to Chicago. Find affordable one-way fares based on user searches. Data last updated aprile 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
mar 6/232:25 pm
TPA
- MDW
1 stop21h 44m
Frontier
Deal found 4/27![Frontier logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
gio 6/49:46 pm
TPA
- ORD
1 stop15h 51m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
gio 5/282:25 pm
TPA
- MDW
1 stop8h 37m
Frontier
Deal found 4/29![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
mar 5/262:25 pm
TPA
- ORD
1 stop18h 30m
Frontier
Deal found 4/29![Frontier logo]()
$76
This Trip.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
mar 6/94:46 pm
TPA
- MDW
1 stop6h 25m
Frontier
Deal found 4/28![Frontier logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
ven 5/1510:25 pm
TPA
- ORD
1 stop21h 19m
Frontier
Deal found 4/24![Frontier logo]()
$78
This Trip.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
mer 5/272:25 pm
TPA
- MDW
1 stop8h 37m
Frontier
Deal found 4/24![Frontier logo]()
$79
This Trip.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
gio 6/42:25 pm
TPA
- ORD
1 stop6h 26m
Frontier
Deal found 4/25![Frontier logo]()
$79
This Super.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
sab 5/161:25 pm
TPA
- ORD
1 stop7h 26m
Frontier
Deal found 4/25![Frontier logo]()
$80
This Trip.com deal was found by Cheapflights users on 4/29. 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.
mar 5/262:25 pm
TPA
- MDW
1 stop8h 37m
Frontier
Deal found 4/29![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
mer 6/34:46 pm
TPA
- ORD
1 stop16h 09m
Frontier
Deal found 4/26![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
mer 5/279:46 pm
TPA
- RFD
1 stop13h 51m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$82
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 aprile 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $148 (Kiwi.com) |
One-way from | $73 (Kiwi.com) |
Popular in | March |
Cheapest in | October |
Average price | $267 |
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 aprile 29, 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
mer 5/27
7:42 pm-9:53 pm
Nonstop3h 11m
Chicago O'Hare Intl
mar 6/2
5:56 pm-9:49 pm
Nonstop2h 53m
$169
TampaChicago
TPA - ORD
TPAORD
Tampa
lun 6/1
7:27 pm-9:38 pm
Nonstop3h 11m
Chicago O'Hare Intl
mer 6/3
8:40 am-3:15 pm
1 stop5h 35m
$190
TampaChicago
TPA - RFD
TPARFD
Tampa
sab 5/30
11:26 am-10:37 am
1 stop24h 11m
Chicago Greater Rockford
gio 6/4
11:27 am-8:51 pm
1 stop8h 24m
$199
TampaChicago
TPA - RFD
TPARFD
Tampa
mer 7/15
8:28 pm-10:37 am
1 stop15h 09m
Chicago Greater Rockford
dom 7/19
11:27 am-7:23 am
1 stop18h 56m
$211
TampaChicago
TPA - RFD
TPARFD
Tampa
sab 8/1
8:28 pm-10:37 am
1 stop15h 09m
Chicago Greater Rockford
gio 8/6
11:37 am-9:19 pm
1 stop8h 42m
$226
TampaChicago
TPA - MDW
TPAMDW
Tampa
mar 6/30
5:15 am-10:09 am
1 stop5h 54m
Chicago Midway
sab 7/4
4:25 pm-12:31 am
1 stop7h 06m
$229
Quickest round-trip
TampaChicago
TPA - MDW
TPAMDW
Tampa
mar 8/11
5:35 pm-7:10 pm
Nonstop2h 35m
Chicago Midway
mar 9/29
7:30 am-11:00 am
Nonstop2h 30m
$229
TampaChicago
TPA - MDW
TPAMDW
Tampa
mar 6/23
5:15 am-10:09 am
1 stop5h 54m
Chicago Midway
sab 6/27
1:21 pm-9:11 pm
1 stop6h 50m
$229
TampaChicago
TPA - RFD
TPARFD
Tampa
mer 5/27
9:46 pm-10:37 am
1 stop13h 51m
Chicago Greater Rockford
lun 6/1
8:03 pm-6:51 pm
2 stops21h 48m
$238
TampaChicago
TPA - MDW
TPAMDW
Tampa
mar 6/23
9:55 pm-11:35 pm
Nonstop2h 40m
Chicago Midway
mer 7/1
5:30 am-9:00 am
Nonstop2h 30m
$241
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-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 aprile 29, 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 afternoon, which can drop the price by up to 13% 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 April 25, 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 aprile 29, 2026.
The most flights from CL9 to CHI are scheduled on a Wednesday (74 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 on average).
How much does it cost to fly round-trip from Clearwater to Chicago?
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 aprile 29, 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
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
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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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 aprile 29, 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 aprile 29, 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 aprile 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$46 | Average$163 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$68 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$70 | Average$179 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$98 | Average$415 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$326 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$348 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$303 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$308 | FlexibilityNo cancel fee | On-time71% |