$106+ Cheap flights from Midway (MDW) to Clearwater, FL
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Oct 17 — Oct 241
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 October or January, booked 82 days in advance, depart on a Wednesday or Friday and return on a Friday
Cheap flight deals from Midway to Clearwater
Cheapest
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 September 17, 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 September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/286:05 pm -
Nonstop2h 40m
Mon 11/25:10 pm -
1 stop4h 05m
Deal found 9/17![Southwest logo]()
$208
This CheapOair deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
1 stop9h 59m
Sat 11/76:29 pm -
1 stop6h 18m
Deal found 9/16![Frontier logo]()
$209
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/41:15 pm -
2 stops6h 35m
Wed 11/114:00 pm -
2 stops6h 30m
Deal found 9/16![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/169:00 pm -
Nonstop2h 35m
Tue 10/2010:35 am -
1 stop5h 05m
Deal found 9/16![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/71:27 pm -
1 stop7h 35m
Mon 10/126:00 am -
1 stop7h 47m
Deal found 9/16![Delta logo]()
$212
This Mytrip deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:16 am -
1 stop10h 06m
Tue 11/35:11 pm -
2 stops19h 11m
Deal found 9/17![Frontier logo]()
$213
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/66:05 pm -
Nonstop2h 40m
Wed 10/77:20 am -
Nonstop2h 40m
Deal found 9/16![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:00 pm -
Nonstop2h 35m
Sat 10/245:55 am -
1 stop8h 10m
Deal found 9/15![Southwest logo]()
$215
This CheapOair deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop9h 59m
Tue 10/275:11 pm -
1 stop7h 36m
Deal found 9/15![Frontier logo]()
$216
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/264:30 pm -
1 stop5h 55m
Wed 10/282:35 pm -
2 stops6h 15m
Deal found 9/16![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/65:00 am -
Nonstop2h 35m
Thu 11/126:50 pm -
Nonstop2h 45m
Deal found 9/16![Southwest logo]()
$218
This Frontier deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/76:25 am -
1 stop9h 53m
Mon 10/125:57 pm -
1 stop6h 46m
Deal found 9/17![Frontier 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 September 17, 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 September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/14. 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 12/103:50 pm -
1 stop5h 20m
Tue 12/154:00 pm -
2 stops6h 25m
Deal found 9/14![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:00 am -
1 stop5h 15m
Tue 12/88:20 am -
1 stop4h 45m
Deal found 9/15![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:25 pm -
1 stop3h 50m
Tue 12/14:25 pm -
1 stop6h 05m
Deal found 9/15![Southwest logo]()
$238
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:45 pm -
2 stops6h 20m
Wed 10/72:35 pm -
2 stops6h 15m
Deal found 9/15![Southwest logo]()
$244
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:27 pm -
1 stop7h 35m
Tue 11/106:20 am -
1 stop6h 39m
Deal found 9/13![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/211:31 pm -
1 stop6h 24m
Thu 11/266:00 am -
1 stop6h 25m
Deal found 9/13![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 9/13. 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 10/138:05 am -
1 stop4h 35m
Tue 10/207:20 am -
Nonstop2h 40m
Deal found 9/13![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:55 am -
Nonstop2h 30m
Sun 11/17:25 am -
Nonstop2h 50m
Deal found 9/15![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 9/14. 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.
Wed 11/41:15 pm -
2 stops6h 35m
Sun 11/89:30 am -
1 stop5h 55m
Deal found 9/14![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:40 pm -
1 stop4h 40m
Fri 10/167:50 pm -
Nonstop2h 45m
Deal found 9/13![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/1711:55 am -
Nonstop2h 35m
Mon 10/197:50 pm -
Nonstop2h 45m
Deal found 9/16![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 11/2012:50 pm -
1 stop3h 55m
Tue 11/245:15 am -
Nonstop2h 45m
Deal found 9/14![Southwest logo]()
$338
Last-minute flights from Midway to ClearwaterDiscover last-minute flight deals from Midway to Clearwater. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Clearwater. Data last updated September 17, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/66:05 pm -
Nonstop2h 40m
Wed 10/77:20 am -
Nonstop2h 40m
Deal found 9/16![Southwest logo]()
$214
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/71:27 pm -
1 stop7h 35m
Mon 10/126:00 am -
1 stop7h 47m
Deal found 9/16![Delta logo]()
$212
This Frontier deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/76:25 am -
1 stop9h 53m
Mon 10/125:57 pm -
1 stop6h 46m
Deal found 9/17![Frontier logo]()
$219
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/169:00 pm -
Nonstop2h 35m
Tue 10/2010:35 am -
1 stop5h 05m
Deal found 9/16![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 10/169:00 pm -
Nonstop2h 35m
Wed 10/217:20 am -
Nonstop2h 40m
Deal found 9/14![Southwest logo]()
$218
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:00 pm -
Nonstop2h 35m
Sat 10/245:55 am -
1 stop8h 10m
Deal found 9/15![Southwest logo]()
$215
This CheapOair deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop9h 59m
Tue 10/275:11 pm -
1 stop7h 36m
Deal found 9/15![Frontier logo]()
$216
This CheapOair deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
1 stop9h 59m
Sat 11/76:29 pm -
1 stop6h 18m
Deal found 9/16![Frontier logo]()
$209
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/264:30 pm -
1 stop5h 55m
Wed 10/282:35 pm -
2 stops6h 15m
Deal found 9/16![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/286:05 pm -
Nonstop2h 40m
Mon 11/25:10 pm -
1 stop4h 05m
Deal found 9/17![Southwest logo]()
$208
This Mytrip deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:16 am -
1 stop10h 06m
Tue 11/35:11 pm -
2 stops19h 11m
Deal found 9/17![Frontier logo]()
$213
This Southwest deal was found by Cheapflights users on 9/14. 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 10/296:25 pm -
1 stop5h 05m
Thu 11/55:10 pm -
1 stop4h 05m
Deal found 9/14![Southwest logo]()
$220
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 September 17, 2026.
Search for one-way flight options from Midway to Clearwater. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 11/171:15 pm -
2 stops6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:46 pm -
1 stop15h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/166:42 pm -
1 stop21h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/152:04 pm -
1 stop16h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Frontier logo]()
$112
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/59:00 pm -
Nonstop2h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$113
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/55:00 am -
Nonstop2h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$114
This Southwest deal was found by Cheapflights users on 9/13. 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 10/132:45 pm -
2 stops6h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$115
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/239:00 pm -
Nonstop2h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$116
This Frontier deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:15 am -
1 stop9h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$117
This Trip.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Fri 12/113:50 pm -
1 stop14h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$118
This KAYAK deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:59 am -
1 stop4h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$119
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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $208 (Southwest) |
One-way from | $106 (Southwest) |
Popular in | June |
Cheapest in | October |
Average price | $253 |
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 7,457,451 searches. Data last updated September 17, 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
Quickest round-trip
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Fri 10/23
9:00 pm-12:35 am
Nonstop2h 35m
Tampa
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$116
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Fri 11/6
4:19 pm-12:18 am
1 stop6h 59m
Tampa
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$126
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Tue 11/24
5:15 am-8:50 am
Nonstop2h 35m
Tampa
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$133
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Fri 10/9
6:40 pm-12:20 am
1 stop4h 40m
Tampa
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$137
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Sat 12/12
4:08 pm-12:25 am
1 stop7h 17m
Tampa
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$151
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Mon 12/14
6:40 pm-10:20 pm
Nonstop2h 40m
Tampa
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$156
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Sun 12/13
6:50 pm-10:25 pm
Nonstop2h 35m
Tampa
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$156
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Sun 12/6
9:37 am-5:02 pm
1 stop6h 25m
Tampa
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$166
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Tue 10/13
6:05 pm-9:45 pm
Nonstop2h 40m
Tampa
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
ChicagoTampa
MDW Chicago Midway - TPA Tampa
MDWTPA
Chicago Midway
Sat 10/3
11:55 am-3:30 pm
Nonstop2h 35m
Tampa
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$197
Showing 1-10 of 22 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 September 17, 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 16% versus a flight in the evening.
How much does it cost to fly round-trip from Chicago Midway Airport to Clearwater?
Airfare is typical for this route at the moment.
Chicago Midway Airport to Clearwater flights typically cost between $160 and $386 in October.The cheapest round-trip price found within the last 5 days was $208 on Southwest (Oct 28-Nov 2).
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 September 12, 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. Monday mornings 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 September 17, 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.
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
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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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 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$193 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$197 | Average$400 | FlexibilityNo cancel fee | On-time63% |