$105+ Cheap flights from Clearwater, FL to Milwaukee (MKE)
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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MKE
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from Clearwater to Milwaukee 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 Milwaukee-Mitchell are usually found in October or May, booked 49 days in advance, depart on a Saturday or Friday and return on a Friday
Cheap flight deals from Clearwater to Milwaukee
Cheapest
Best
Last-minute
One-way
Cheapest flights from Clearwater to MilwaukeeExplore the most affordable flight options available from Clearwater to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
Explore the most affordable flight options available from Clearwater to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
This Southwest deal was found by Cheapflights users on 8/17. 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 9/911:40 am -
Nonstop2h 45m
Wed 9/1610:50 am -
Nonstop2h 40m
Deal found 8/17![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/911:40 am -
Nonstop2h 45m
Mon 9/146:25 am -
1 stop7h 55m
Deal found 8/18![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 8/16. 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 9/98:45 am -
1 stop6h 05m
Mon 9/146:37 pm -
1 stop4h 51m
Deal found 8/16![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 11/218:50 pm -
Nonstop2h 50m
Thu 11/266:30 am -
1 stop8h 50m
Deal found 8/18![Southwest logo]()
$288
This Southwest deal was found by Cheapflights users on 8/17. 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.
Fri 9/112:25 pm -
Nonstop2h 45m
Mon 9/146:25 am -
1 stop7h 55m
Deal found 8/17![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:15 am -
1 stop4h 51m
Mon 9/144:49 pm -
1 stop6h 39m
Deal found 8/17![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 11/95:40 am -
1 stop7h 25m
Fri 11/134:50 pm -
2 stops5h 40m
Deal found 8/21![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 12/117:55 pm -
Nonstop2h 55m
Mon 12/1410:45 am -
Nonstop2h 45m
Deal found 8/21![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/1511:35 am -
2 stops9h 25m
Tue 9/227:50 am -
2 stops8h 15m
Deal found 8/19![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/2411:30 am -
2 stops10h 55m
Mon 9/284:20 pm -
1 stop4h 40m
Deal found 8/20![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/172:25 pm -
Nonstop2h 45m
Thu 9/244:20 pm -
1 stop6h 10m
Deal found 8/18![Southwest logo]()
$315
Best flights from Clearwater to MilwaukeeDiscover carefully curated flight deals from Clearwater to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
Discover carefully curated flight deals from Clearwater to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:00 am -
1 stop7h 44m
Mon 10/196:51 pm -
1 stop4h 27m
Deal found 8/18![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 8/17. 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.
Fri 10/169:10 pm -
Nonstop2h 50m
Mon 10/193:45 pm -
Nonstop2h 40m
Deal found 8/17![Southwest logo]()
$292
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Sun 9/137:30 am -
1 stop5h 00m
Wed 9/166:00 am -
2 stops8h 28m
Deal found 8/18![United Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/276:20 am -
1 stop6h 09m
Thu 10/295:30 am -
1 stop7h 29m
Deal found 8/20![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/219:20 am -
Nonstop2h 50m
Sun 10/256:05 pm -
1 stop6h 25m
Deal found 8/19![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/49:25 am -
Nonstop2h 50m
Thu 10/86:20 am -
1 stop5h 25m
Deal found 8/20![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 10/45:15 am -
1 stop4h 51m
Thu 10/85:30 am -
1 stop7h 29m
Deal found 8/21![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 10/188:35 pm -
Nonstop2h 50m
Mon 10/196:20 am -
1 stop5h 25m
Deal found 8/18![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/1311:50 am -
Nonstop2h 45m
Wed 9/1610:50 am -
Nonstop2h 40m
Deal found 8/18![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/282:25 pm -
Nonstop2h 45m
Tue 9/2910:50 am -
Nonstop2h 40m
Deal found 8/21![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/144:30 pm -
2 stops6h 45m
Sun 10/187:05 am -
1 stop4h 05m
Deal found 8/19![Southwest logo]()
$367
Last-minute flights from Clearwater to MilwaukeeDiscover last-minute flight deals from Clearwater to Milwaukee. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Clearwater to Milwaukee. Data last updated August 21, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/17. 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 9/911:40 am -
Nonstop2h 45m
Wed 9/1610:50 am -
Nonstop2h 40m
Deal found 8/17![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/911:40 am -
Nonstop2h 45m
Mon 9/146:25 am -
1 stop7h 55m
Deal found 8/18![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 8/16. 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 9/98:45 am -
1 stop6h 05m
Mon 9/146:37 pm -
1 stop4h 51m
Deal found 8/16![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 8/17. 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.
Fri 9/112:25 pm -
Nonstop2h 45m
Mon 9/146:25 am -
1 stop7h 55m
Deal found 8/17![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:15 am -
1 stop4h 51m
Mon 9/144:49 pm -
1 stop6h 39m
Deal found 8/17![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/1511:35 am -
2 stops9h 25m
Tue 9/227:50 am -
2 stops8h 15m
Deal found 8/19![Southwest logo]()
$312
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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.
Wed 9/167:30 am -
1 stop5h 00m
Wed 9/236:00 am -
2 stops8h 28m
Deal found 8/19![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/172:25 pm -
Nonstop2h 45m
Thu 9/244:20 pm -
1 stop6h 10m
Deal found 8/18![Southwest logo]()
$315
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/211:05 pm -
1 stop7h 28m
Tue 9/228:03 am -
1 stop5h 05m
Deal found 8/21![American Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/2411:30 am -
2 stops10h 55m
Mon 9/284:20 pm -
1 stop4h 40m
Deal found 8/20![Southwest logo]()
$313
One-way flights from Clearwater to MilwaukeeSearch for one-way flight options from Clearwater to Milwaukee. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
Search for one-way flight options from Clearwater to Milwaukee. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/226:00 pm -
2 stops40h 08m
Deal found 8/21![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:00 pm -
2 stops40h 20m
Deal found 8/21![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/232:10 pm -
2 stops19h 58m
Deal found 8/20![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1912:50 pm -
2 stops21h 30m
Deal found 8/17![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/162:10 pm -
2 stops19h 58m
Deal found 8/18![Frontier logo]()
$137
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 10/316:45 am -
Nonstop2h 45m
Deal found 8/18![Southwest logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/215:57 pm -
2 stops26h 18m
Deal found 8/20![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
2 stops37h 08m
Deal found 8/17![Frontier logo]()
$141
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:13 pm -
1 stop6h 37m
Deal found 8/18![United Airlines logo]()
$144
Find flight deals from Clearwater to Milwaukee
Keep the following information in mind while searching for Clearwater to Milwaukee flight deals. Data was last updated August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $277 (Southwest) |
One-way from | $105 (Kiwi.com) |
Popular in | January |
Cheapest in | October |
Average price | $446 |
Cheapflights Fare Finder
Customize your flight search to find flights from Clearwater to Milwaukee 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 August 21, 2026.
Use the filters below to find and compare flights from Clearwater to Milwaukee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
TampaMilwaukee
TPA Tampa - MKE Milwaukee-Mitchell
TPAMKE
Tampa
Mon 10/12
6:00 am-12:44 pm
1 stop7h 44m
Milwaukee-Mitchell
Mon 10/19
6:51 pm-12:18 am
1 stop4h 27m
$287
TampaMilwaukee
TPA Tampa - MKE Milwaukee-Mitchell
TPAMKE
Tampa
Tue 10/27
6:20 am-11:29 am
1 stop6h 09m
Milwaukee-Mitchell
Thu 10/29
5:30 am-1:59 pm
1 stop7h 29m
$287
TampaMilwaukee
TPA Tampa - MKE Milwaukee-Mitchell
TPAMKE
Tampa
Fri 10/16
9:10 pm-11:00 pm
Nonstop2h 50m
Milwaukee-Mitchell
Mon 10/19
3:45 pm-7:25 pm
Nonstop2h 40m
$292
TampaMilwaukee
TPA Tampa - MKE Milwaukee-Mitchell
TPAMKE
Tampa
Wed 10/21
9:20 am-11:10 am
Nonstop2h 50m
Milwaukee-Mitchell
Sun 10/25
6:05 pm-1:30 am
1 stop6h 25m
$337
TampaMilwaukee
TPA Tampa - MKE Milwaukee-Mitchell
TPAMKE
Tampa
Sun 10/4
9:25 am-11:15 am
Nonstop2h 50m
Milwaukee-Mitchell
Thu 10/8
6:20 am-12:45 pm
1 stop5h 25m
$342
TampaMilwaukee
TPA Tampa - MKE Milwaukee-Mitchell
TPAMKE
Tampa
Sun 10/4
5:15 am-9:06 am
1 stop4h 51m
Milwaukee-Mitchell
Thu 10/8
5:30 am-1:59 pm
1 stop7h 29m
$342
TampaMilwaukee
TPA Tampa - MKE Milwaukee-Mitchell
TPAMKE
Tampa
Sun 10/18
8:35 pm-10:25 pm
Nonstop2h 50m
Milwaukee-Mitchell
Mon 10/19
6:20 am-12:45 pm
1 stop5h 25m
$342
TampaMilwaukee
TPA Tampa - MKE Milwaukee-Mitchell
TPAMKE
Tampa
Sun 9/13
7:30 am-11:30 am
1 stop5h 00m
Milwaukee-Mitchell
Wed 9/16
6:00 am-3:28 pm
2 stops8h 28m
$347
Quickest round-trip
TampaMilwaukee
TPA Tampa - MKE Milwaukee-Mitchell
TPAMKE
Tampa
Sun 9/13
11:50 am-1:35 pm
Nonstop2h 45m
Milwaukee-Mitchell
Wed 9/16
10:50 am-2:30 pm
Nonstop2h 40m
$357
TampaMilwaukee
TPA Tampa - MKE Milwaukee-Mitchell
TPAMKE
Tampa
Mon 9/28
2:25 pm-4:10 pm
Nonstop2h 45m
Milwaukee-Mitchell
Tue 9/29
10:50 am-2:30 pm
Nonstop2h 40m
$357
Showing 1-10 of 23 resultsSorted by cheapest first
Best time to book a flight from Clearwater to Milwaukee
Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Clearwater with our price prediction graph.
TPA-MKE
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 Milwaukee
CL9-MKE
TPA-MKE
What is the cheapest time of day to fly from CL9 to MKE?
Find hourly flight availability from Clearwater to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 21, 2026.
One of the essential ways to save on airfare from Clearwater to Milwaukee is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 19% on airfare.
How much does it cost to fly round-trip from Clearwater to Milwaukee?
Airfare is below average for this route at the moment.
Clearwater to Milwaukee flights typically cost between $397 and $572 in September.The cheapest round-trip price found within the last 5 days was $277 on Southwest (Sep 9-Sep 12).
What is the cheapest day to fly from Clearwater to Milwaukee?
Use this chart to determine the cheapest time to fly round-trip from Clearwater to Milwaukee. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their Clearwater to Milwaukee flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Milwaukee
Get insights into the airlines that provide service to Milwaukee. 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 Milwaukee. Reviews last updated August 21, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Clearwater to Milwaukee have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
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 Milwaukee. 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 Milwaukee?
Book flights to Milwaukee if you plan to visit one of these locationsSheboygan
Port Washington
New Berlin
Oak Creek
Wauwatosa
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Alternative routes for Clearwater to Milwaukee
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Milwaukee by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Clearwater to Milwaukee by cabin class
Find flights from Clearwater to Milwaukee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Milwaukee
Explore flights to Milwaukee departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 21, 2026.
Clearwater and Milwaukee flights
Browse other Clearwater and Milwaukee flight options. Last updated on August 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Clearwater to Milwaukee flights
Consider these flights traveling from Clearwater to Milwaukee.
Top 5 airlines flying from Clearwater to Milwaukee
Discover the top 5 airlines that operate flights from Clearwater to Milwaukee. 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 August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$226 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$133 | Average$403 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$167 | Average$377 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$194 | Average$397 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$249 | Average$429 | FlexibilityNo cancel fee | On-time63% |