$99+ Cheap flights from Midway (MDW) to Clearwater, FL
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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Jul 15 — Jul 221
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Clearwater 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 Chicago Midway to Clearwater are usually found in September or October, booked 22 days in advance, depart on a Friday or Wednesday and return on a Friday
Cheap flight deals from Midway to Clearwater
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Best
Last-minute
One-way
Cheapest flights from Midway to ClearwaterExplore the most affordable flight options available from Midway to Clearwater. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 15, 2026.
Explore the most affordable flight options available from Midway to Clearwater. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:00 am
MDW
- TPA
1 stop11h 51m
Frontier
Tue 9/157:00 am
TPA
- MDW
1 stop4h 58m
Frontier
Deal found 6/10![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:04 pm
MDW
- TPA
1 stop5h 47m
Frontier
Tue 8/254:46 pm
TPA
- MDW
1 stop6h 25m
Frontier
Deal found 6/11![Frontier logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:11 pm
MDW
- TPA
1 stop5h 41m
Frontier
Wed 8/125:40 pm
TPA
- MDW
1 stop5h 23m
Frontier
Deal found 6/10![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:05 am
MDW
- TPA
1 stop11h 47m
Frontier
Wed 8/55:40 pm
TPA
- MDW
1 stop5h 23m
Frontier
Deal found 6/10![Frontier logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:00 am
MDW
- TPA
1 stop11h 51m
Frontier
Thu 9/107:00 am
TPA
- MDW
1 stop4h 58m
Frontier
Deal found 6/10![Frontier logo]()
$208
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:25 am
MDW
- TPA
Nonstop2h 30m
Southwest
Tue 7/149:55 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Deal found 6/11![Southwest logo]()
$209
This Frontier deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:25 am
MDW
- TPA
1 stop8h 53m
Frontier
Tue 11/1012:54 pm
TPA
- MDW
1 stop9h 59m
Frontier
Deal found 6/14![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:03 pm
MDW
- TPA
1 stop9h 56m
Frontier
Wed 10/2812:54 pm
TPA
- MDW
1 stop9h 59m
Frontier
Deal found 6/12![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:11 pm
MDW
- TPA
1 stop5h 41m
Frontier
Wed 7/224:46 pm
TPA
- MDW
1 stop6h 17m
Frontier
Deal found 6/10![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:05 am
MDW
- TPA
1 stop11h 30m
Frontier
Wed 8/122:10 pm
TPA
- MDW
1 stop8h 53m
Frontier
Deal found 6/10![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- TPA
1 stop11h 47m
Frontier
Tue 7/212:25 pm
TPA
- MDW
1 stop8h 38m
Frontier
Deal found 6/10![Frontier logo]()
$217
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:20 am
MDW
- TPA
1 stop4h 20m
Southwest
Tue 7/219:55 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Deal found 6/10![Southwest logo]()
$219
Best flights from Midway to ClearwaterDiscover carefully curated flight deals from Midway to Clearwater that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 15, 2026.
Discover carefully curated flight deals from Midway to Clearwater that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 15, 2026.
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:25 pm
MDW
- TPA
Nonstop2h 40m
Southwest
Wed 8/56:00 am
TPA
- MDW
1 stop5h 30m
Southwest
Deal found 6/11![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:30 am
MDW
- TPA
2 stops6h 50m
Southwest
Tue 7/2111:55 am
TPA
- MDW
1 stop4h 55m
Southwest
Deal found 6/10![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/108:10 pm
MDW
- TPA
Nonstop2h 40m
Southwest
Wed 7/159:55 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Deal found 6/11![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/92:30 pm
MDW
- TPA
1 stop6h 25m
Southwest
Tue 7/146:30 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Deal found 6/10![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:25 am
MDW
- TPA
Nonstop2h 30m
Southwest
Wed 7/2911:55 am
TPA
- MDW
1 stop4h 55m
Southwest
Deal found 6/13![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/410:10 am
MDW
- TPA
1 stop6h 00m
Southwest
Sat 8/87:25 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/13![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/143:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Sun 8/167:00 am
TPA
- MDW
1 stop4h 05m
Southwest
Deal found 6/10![Southwest logo]()
$361
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:20 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Tue 8/117:35 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/14![Southwest logo]()
$361
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:10 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Wed 8/195:35 pm
TPA
- MDW
Nonstop2h 35m
Southwest
Deal found 6/14![Southwest logo]()
$361
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/178:10 pm
MDW
- TPA
Nonstop2h 40m
Southwest
Tue 7/215:40 am
TPA
- MDW
1 stop6h 05m
Southwest
Deal found 6/12![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/205:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Mon 7/275:20 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 6/14![Southwest logo]()
$373
Last-minute flights from Midway to ClearwaterDiscover last-minute flight deals from Midway to Clearwater. Data last updated June 15, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Clearwater. Data last updated June 15, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:05 am
MDW
- TPA
1 stop11h 47m
Frontier
Tue 7/144:46 pm
TPA
- MDW
1 stop6h 17m
Frontier
Deal found 6/10![Frontier logo]()
$228
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:25 am
MDW
- TPA
Nonstop2h 30m
Southwest
Tue 7/149:55 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Deal found 6/11![Southwest logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- TPA
1 stop11h 47m
Frontier
Tue 7/212:25 pm
TPA
- MDW
1 stop8h 38m
Frontier
Deal found 6/10![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:11 pm
MDW
- TPA
1 stop5h 41m
Frontier
Wed 7/224:46 pm
TPA
- MDW
1 stop6h 17m
Frontier
Deal found 6/10![Frontier logo]()
$213
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
MDW
- TPA
1 stop5h 39m
Delta
Tue 7/2111:14 am
TPA
- MDW
1 stop6h 01m
Delta
Deal found 6/11![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:20 am
MDW
- TPA
1 stop4h 20m
Southwest
Tue 7/219:55 pm
TPA
- MDW
Nonstop2h 45m
Southwest
Deal found 6/10![Southwest logo]()
$219
This Trip.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2212:11 pm
MDW
- TPA
1 stop5h 41m
Frontier
Wed 8/510:27 am
TPA
- MDW
1 stop6h 23m
Frontier
Deal found 6/13![Frontier logo]()
$227
This Trip.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2512:11 pm
MDW
- TPA
1 stop6h 39m
Frontier
Tue 8/44:46 pm
TPA
- MDW
1 stop6h 17m
Frontier
Deal found 6/11![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:05 am
MDW
- TPA
1 stop11h 47m
Frontier
Wed 8/55:40 pm
TPA
- MDW
1 stop5h 23m
Frontier
Deal found 6/10![Frontier logo]()
$207
This Frontier deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:05 am
MDW
- TPA
1 stop11h 47m
Frontier
Tue 8/42:25 pm
TPA
- MDW
1 stop8h 38m
Frontier
Deal found 6/10![Frontier logo]()
$220
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/288:15 pm
MDW
- TPA
Nonstop2h 40m
Southwest
Wed 8/57:55 am
TPA
- MDW
1 stop5h 25m
Southwest
Deal found 6/10![Southwest logo]()
$225
This Trip.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2812:11 pm
MDW
- TPA
1 stop5h 41m
Frontier
Tue 8/1110:27 am
TPA
- MDW
1 stop7h 24m
Frontier
Deal found 6/11![Frontier logo]()
$226
One-way flights from Midway to ClearwaterSearch for one-way flight options from Midway to Clearwater. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
Search for one-way flight options from Midway to Clearwater. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:00 am
MDW
- TPA
1 stop14h 29m
Frontier
Deal found 6/10![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:05 am
MDW
- TPA
1 stop15h 10m
Frontier
Deal found 6/10![Frontier logo]()
$101
This Trip.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:11 pm
MDW
- TPA
1 stop5h 41m
Frontier
Deal found 6/10![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:17 pm
MDW
- TPA
1 stop14h 20m
Frontier
Deal found 6/10![Frontier logo]()
$109
This Frontier deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:03 pm
MDW
- TPA
1 stop9h 54m
Frontier
Deal found 6/13![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- TPA
1 stop14h 11m
Frontier
Deal found 6/10![Frontier logo]()
$112
This Super.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/712:11 pm
MDW
- TPA
1 stop5h 41m
Frontier
Deal found 6/14![Frontier logo]()
$114
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/711:05 am
MDW
- TPA
1 stop4h 53m
Delta
Deal found 6/10![Delta logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:00 am
MDW
- TPA
1 stop12h 45m
Frontier
Deal found 6/10![Frontier logo]()
$116
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:20 pm
MDW
- TPA
1 stop3h 50m
Southwest
Deal found 6/10![Southwest logo]()
$117
Find flight deals from Midway to Clearwater
Keep the following information in mind while searching for Midway to Clearwater flight deals. Data was last updated June 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $191 (Kiwi.com) |
One-way from | $99 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $366 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Clearwater that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 15, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Clearwater that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 8/1
6:25 pm-10:05 pm
Nonstop2h 40m
Tampa
Wed 8/5
6:00 am-10:30 am
1 stop5h 30m
$295
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sat 7/18
6:30 am-2:20 pm
2 stops6h 50m
Tampa
Tue 7/21
11:55 am-3:50 pm
1 stop4h 55m
$304
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Fri 7/10
8:10 pm-11:50 pm
Nonstop2h 40m
Tampa
Wed 7/15
9:55 pm-11:40 pm
Nonstop2h 45m
$311
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Thu 7/9
2:30 pm-9:55 pm
1 stop6h 25m
Tampa
Tue 7/14
6:30 pm-8:15 pm
Nonstop2h 45m
$321
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Tue 7/21
5:25 am-8:55 am
Nonstop2h 30m
Tampa
Wed 7/29
11:55 am-3:50 pm
1 stop4h 55m
$359
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Tue 8/4
10:10 am-5:10 pm
1 stop6h 00m
Tampa
Sat 8/8
7:25 am-9:05 am
Nonstop2h 40m
$359
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Fri 8/14
3:15 pm-6:50 pm
Nonstop2h 35m
Tampa
Sun 8/16
7:00 am-10:05 am
1 stop4h 05m
$361
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Sun 8/9
6:20 pm-9:55 pm
Nonstop2h 35m
Tampa
Tue 8/11
7:35 am-9:15 am
Nonstop2h 40m
$361
Quickest round-trip
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Thu 8/13
8:10 pm-11:45 pm
Nonstop2h 35m
Tampa
Wed 8/19
5:35 pm-7:10 pm
Nonstop2h 35m
$361
ChicagoTampa
MDW - TPA
MDWTPA
Chicago Midway
Fri 7/17
8:10 pm-11:50 pm
Nonstop2h 40m
Tampa
Tue 7/21
5:40 am-10:45 am
1 stop6h 05m
$371
Showing 1-10 of 23 resultsSorted by cheapest first
Best time to book a flight from Midway to Clearwater
Have a flexible travel schedule? Discover the best time to fly to Clearwater from Midway with our price prediction graph.
MDW-TPA
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 Chicago Midway Airport to Clearwater
MDW-CL9
MDW-TPA
What is the cheapest time of day to fly from MDW to CL9?
Find hourly flight availability from Midway to Clearwater. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 15, 2026.
When flying from Chicago Midway Airport to Clearwater, 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 19% versus a flight in the evening.
Weekly flight availability from Chicago Midway Airport to Clearwater
Explore weekly flight availability from Midway to Clearwater. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 15, 2026.
The most flights from MDW to CL9 are scheduled on a Saturday (14 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Chicago Midway Airport to Clearwater?
What is the cheapest day to fly from Chicago Midway Airport to Clearwater?
Use this chart to determine the cheapest time to fly round-trip from Midway to Clearwater. Price data was last updated on June 13, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Clearwater flight should consider departing on Monday at noon 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 Clearwater
Get insights into the airlines that provide service to Clearwater. 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 Clearwater. Reviews last updated June 15, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Clearwater, such as Southwest and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Crew
8.6
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Midway to Clearwater. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to Clearwater
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Clearwater by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Clearwater by cabin class
Find flights from Midway to Clearwater, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Clearwater flights
Browse other Midway and Clearwater flight options. Last updated on June 15, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on June 15, 2026.
Popular flight searches
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Midway to Clearwater flights
Consider these flights traveling from Midway to Clearwater.
Top 2 airlines flying from Midway to Clearwater
Discover the top 2 airlines that operate flights from Midway to Clearwater. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$70 | Average$176 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$174 | Average$381 | FlexibilityNo cancel fee | On-time63% |