$117+ Cheap flights from Clearwater, FL to Midway (MDW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Sep 1 — Sep 81
Round-trip
1 adult, Economy
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Find cheap flights from Clearwater to Midway 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 Midway are usually found in October or November, booked 60 days in advance, depart on a Friday or Wednesday and return on a Friday
Cheap flight deals from Clearwater to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Clearwater to MidwayExplore the most affordable flight options available from Clearwater to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.
Explore the most affordable flight options available from Clearwater to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:10 pm
TPA
- MDW
1 stop8h 53m
Frontier
Thu 8/2711:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Deal found 7/31![Frontier logo]()
$212
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Tue 8/2511:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Deal found 7/31![Frontier logo]()
$213
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:15 am
TPA
- MDW
Nonstop2h 40m
Southwest
Mon 9/146:20 pm
MDW
- TPA
Nonstop2h 40m
Southwest
Deal found 7/29![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:30 am
TPA
- MDW
1 stop4h 00m
Southwest
Mon 8/246:20 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 7/29![Southwest logo]()
$215
This Super.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 pm
TPA
- MDW
1 stop6h 44m
Frontier
Sun 9/276:25 am
MDW
- TPA
1 stop10h 00m
Frontier
Deal found 7/31![Frontier logo]()
$216
This Delta deal was found by Cheapflights users on 7/28. 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.
Tue 8/258:15 am
TPA
- MDW
1 stop5h 24m
Delta
Wed 9/26:05 am
MDW
- TPA
1 stop5h 24m
Delta
Deal found 7/28![Delta logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:05 am
TPA
- MDW
2 stops14h 26m
Frontier
Mon 8/2411:50 am
MDW
- TPA
1 stop11h 45m
Frontier
Deal found 7/31![Frontier logo]()
$218
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:35 pm
TPA
- MDW
1 stop6h 45m
Southwest
Thu 9/33:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 7/30![Southwest logo]()
$219
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Thu 9/36:05 am
MDW
- TPA
1 stop11h 44m
Frontier
Deal found 7/30![Frontier logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Thu 8/2011:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Deal found 7/29![Frontier logo]()
$221
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/253:00 pm
TPA
- MDW
1 stop5h 35m
Southwest
Wed 8/266:00 am
MDW
- TPA
2 stops7h 05m
Southwest
Deal found 7/30![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 7/28. 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.
Tue 8/255:55 pm
TPA
- MDW
1 stop5h 41m
Delta
Sat 8/296:11 am
MDW
- TPA
1 stop4h 18m
Delta
Deal found 7/28![Delta logo]()
$223
Best flights from Clearwater to MidwayDiscover carefully curated flight deals from Clearwater to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2026.
Discover carefully curated flight deals from Clearwater to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2026.
This Southwest deal was found by Cheapflights users on 7/28. 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.
Thu 10/2211:00 am
TPA
- MDW
1 stop5h 00m
Southwest
Mon 10/267:05 am
MDW
- TPA
1 stop3h 55m
Southwest
Deal found 7/28![Southwest logo]()
$220
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:13 pm
TPA
- MDW
1 stop6h 51m
Delta
Mon 12/75:09 pm
MDW
- TPA
1 stop6h 16m
Delta
Deal found 7/29![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:20 pm
TPA
- MDW
1 stop4h 00m
Southwest
Tue 10/61:35 pm
MDW
- TPA
2 stops6h 20m
Southwest
Deal found 7/30![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:10 pm
TPA
- MDW
1 stop4h 10m
Southwest
Tue 9/87:30 am
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 7/31![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 pm
TPA
- MDW
Nonstop2h 40m
Southwest
Mon 11/26:50 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 8/1![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:15 am
TPA
- MDW
Nonstop2h 40m
Southwest
Sat 9/53:05 pm
MDW
- TPA
Nonstop2h 40m
Southwest
Deal found 7/31![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:25 am
TPA
- MDW
1 stop6h 25m
Southwest
Mon 9/2812:10 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 7/31![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:35 am
TPA
- MDW
1 stop6h 15m
Southwest
Fri 9/47:55 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 8/1![Southwest logo]()
$263
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:25 pm
TPA
- MDW
Nonstop2h 35m
Southwest
Mon 8/317:55 pm
MDW
- TPA
Nonstop2h 30m
Southwest
Deal found 7/31![Southwest logo]()
$272
Last-minute flights from Clearwater to MidwayDiscover last-minute flight deals from Clearwater to Midway. Data last updated August 2, 2026 and is based on user searches.
Discover last-minute flight deals from Clearwater to Midway. Data last updated August 2, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:10 pm
TPA
- MDW
1 stop8h 53m
Frontier
Thu 8/2711:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Deal found 7/31![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
Mon 8/175:40 pm
TPA
- MDW
1 stop5h 23m
Frontier
Thu 8/206:05 am
MDW
- TPA
1 stop11h 44m
Frontier
Deal found 7/28![Frontier logo]()
$214
This Delta deal was found by Cheapflights users on 7/28. 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.
Tue 8/186:20 am
TPA
- MDW
1 stop4h 39m
Delta
Wed 8/1910:54 am
MDW
- TPA
1 stop6h 59m
Delta
Deal found 7/28![Delta logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Thu 8/2011:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Deal found 7/29![Frontier logo]()
$221
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:00 pm
TPA
- MDW
1 stop5h 55m
Southwest
Thu 8/203:20 pm
MDW
- TPA
1 stop3h 55m
Southwest
Deal found 7/29![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:30 am
TPA
- MDW
1 stop4h 00m
Southwest
Mon 8/246:20 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 7/29![Southwest logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:05 am
TPA
- MDW
2 stops14h 26m
Frontier
Mon 8/2411:50 am
MDW
- TPA
1 stop11h 45m
Frontier
Deal found 7/31![Frontier logo]()
$218
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Tue 8/2511:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Deal found 7/31![Frontier logo]()
$213
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/253:00 pm
TPA
- MDW
1 stop5h 35m
Southwest
Wed 8/266:00 am
MDW
- TPA
2 stops7h 05m
Southwest
Deal found 7/30![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:35 pm
TPA
- MDW
1 stop6h 45m
Southwest
Thu 9/33:15 pm
MDW
- TPA
Nonstop2h 35m
Southwest
Deal found 7/30![Southwest logo]()
$219
This Frontier deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Fri 9/411:50 am
MDW
- TPA
1 stop5h 59m
Frontier
Deal found 8/2![Frontier logo]()
$211
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Thu 9/36:05 am
MDW
- TPA
1 stop11h 44m
Frontier
Deal found 7/30![Frontier logo]()
$220
One-way flights from Clearwater to MidwaySearch for one-way flight options from Clearwater to Midway. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
Search for one-way flight options from Clearwater to Midway. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:25 pm
TPA
- MDW
1 stop21h 25m
Frontier
Deal found 7/29![Frontier logo]()
$117
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:15 am
TPA
- MDW
Nonstop2h 40m
Southwest
Deal found 7/31![Southwest logo]()
$118
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:20 am
TPA
- MDW
2 stops7h 45m
Southwest
Deal found 7/30![Southwest logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:05 am
TPA
- MDW
2 stops14h 26m
Frontier
Deal found 7/31![Frontier logo]()
$122
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:10 pm
TPA
- MDW
1 stop4h 05m
Southwest
Deal found 8/1![Southwest logo]()
$123
This Super.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:27 am
TPA
- MDW
1 stop6h 23m
Frontier
Deal found 8/1![Frontier logo]()
$125
This Trip.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Deal found 7/29![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:05 am
TPA
- MDW
2 stops14h 26m
Frontier
Deal found 7/30![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:31 pm
TPA
- MDW
2 stops25h 16m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/32:25 pm
TPA
- MDW
1 stop9h 22m
Frontier
Deal found 8/1![Frontier logo]()
$129
Find flight deals from Clearwater to Midway
Keep the following information in mind while searching for Clearwater to Midway flight deals. Data was last updated August 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $211 (Frontier) |
One-way from | $117 (Kiwi.com) |
Popular in | March |
Cheapest in | October |
Average price | $268 |
Cheapflights Fare Finder
Customize your flight search to find flights from Clearwater to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 2, 2026.
Use the filters below to find and compare flights from Clearwater to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
TampaChicago
TPA - MDW
TPAMDW
Tampa
Thu 10/22
11:00 am-3:00 pm
1 stop5h 00m
Chicago Midway
Mon 10/26
7:05 am-12:00 pm
1 stop3h 55m
$220
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 10/3
12:20 pm-3:20 pm
1 stop4h 00m
Chicago Midway
Tue 10/6
1:35 pm-8:55 pm
2 stops6h 20m
$228
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 12/5
12:13 pm-6:04 pm
1 stop6h 51m
Chicago Midway
Mon 12/7
5:09 pm-12:25 am
1 stop6h 16m
$229
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 9/5
4:10 pm-7:20 pm
1 stop4h 10m
Chicago Midway
Tue 9/8
7:30 am-11:00 am
Nonstop2h 30m
$232
TampaChicago
TPA - MDW
TPAMDW
Tampa
Tue 10/20
6:00 pm-7:40 pm
Nonstop2h 40m
Chicago Midway
Mon 11/2
6:50 pm-10:25 pm
Nonstop2h 35m
$235
TampaChicago
TPA - MDW
TPAMDW
Tampa
Thu 9/3
5:15 am-6:55 am
Nonstop2h 40m
Chicago Midway
Sat 9/5
3:05 pm-6:45 pm
Nonstop2h 40m
$240
TampaChicago
TPA - MDW
TPAMDW
Tampa
Tue 9/22
6:25 am-11:50 am
1 stop6h 25m
Chicago Midway
Mon 9/28
12:10 pm-3:45 pm
Nonstop2h 35m
$245
TampaChicago
TPA - MDW
TPAMDW
Tampa
Wed 9/2
10:35 am-3:50 pm
1 stop6h 15m
Chicago Midway
Fri 9/4
7:55 pm-11:30 pm
Nonstop2h 35m
$263
Quickest round-trip
TampaChicago
TPA - MDW
TPAMDW
Tampa
Fri 8/28
5:25 pm-7:00 pm
Nonstop2h 35m
Chicago Midway
Mon 8/31
7:55 pm-11:25 pm
Nonstop2h 30m
$272
Cheapest one-way
TampaChicago
TPA - MDW
TPAMDW
Tampa
Sat 12/5
3:30 pm-5:15 pm
Nonstop2h 45m
$118
Showing 1-10 of 20 resultsSorted by cheapest first
Best time to book a flight from Clearwater to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Clearwater with our price prediction graph.
TPA-MDW
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 Midway Airport
CL9-MDW
TPA-MDW
What is the cheapest time of day to fly from CL9 to MDW?
Find hourly flight availability from Clearwater to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 2, 2026.
It’s optimal to fly from Clearwater to Chicago Midway Airport in the evening. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight in the morning.
How much does it cost to fly round-trip from Clearwater to Chicago Midway Airport?
Airfare is typical for this route at the moment.
Clearwater to Chicago Midway Airport flights typically cost between $209 and $426 in August.The cheapest round-trip price found within the last 5 days was $211 on Frontier (Aug 28-Sep 4).
What is the cheapest day to fly from Clearwater to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Clearwater to Midway. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their Clearwater to Chicago Midway Airport flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated August 2, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andJetBlue from Clearwater to Chicago Midway Airport 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
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Clearwater to Midway. 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 Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Clearwater to Midway
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 2, 2026.
Clearwater and Midway flights
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Clearwater to Midway flights
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Top 4 airlines flying from Clearwater to Midway
Discover the top 4 airlines that operate flights from Clearwater to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$46 | Average$183 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$240 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$168 | Average$371 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$202 | Average$360 | FlexibilityNo cancel fee | On-time62% |