$85+ Cheap flights from Milwaukee (MKE) to Kissimmee, 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MCO
jun. 27 — jul. 41
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee to Kissimmee 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
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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 Milwaukee-Mitchell to Kissimmee are usually found in January or February, booked 83 days in advance, depart on a Thursday or Tuesday and return on a Wednesday
Cheap flight deals from Milwaukee to Kissimmee
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Last-minute
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Cheapest flights from Milwaukee to KissimmeeExplore the most affordable flight options available from Milwaukee to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on mayo 28, 2026.
Explore the most affordable flight options available from Milwaukee to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on mayo 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/128:10 pm
MKE
- MCO
Nonstop2h 47m
Frontier
sáb. 10/175:02 pm
MCO
- MKE
Nonstop3h 13m
Frontier
Deal found 5/23![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/18:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
mar. 9/86:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 5/26![Frontier logo]()
$168
This Frontier deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/18:10 pm
MKE
- MCO
Nonstop2h 47m
Frontier
lun. 10/55:02 pm
MCO
- MKE
Nonstop3h 13m
Frontier
Deal found 5/26![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/158:10 pm
MKE
- MCO
Nonstop2h 47m
Frontier
lun. 10/195:02 pm
MCO
- MKE
Nonstop3h 13m
Frontier
Deal found 5/27![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/258:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
mar. 9/16:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 5/27![Frontier logo]()
$177
This Super.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/308:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
mar. 7/76:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 5/26![Frontier logo]()
$183
This Frontier deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/148:43 am
MKE
- MCO
Nonstop2h 53m
Frontier
mar. 7/216:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 5/27![Frontier logo]()
$190
This Frontier deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/208:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
mar. 8/256:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 5/27![Frontier logo]()
$202
This Frontier deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/68:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
jue. 9/105:02 pm
MCO
- MKE
Nonstop3h 13m
Frontier
Deal found 5/27![Frontier logo]()
$206
This Super.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/48:43 am
MKE
- MCO
Nonstop2h 53m
Frontier
mar. 8/116:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 5/26![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/258:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
jue. 8/276:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 5/27![Frontier logo]()
$210
Best flights from Milwaukee to KissimmeeDiscover carefully curated flight deals from Milwaukee to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated mayo 28, 2026.
Discover carefully curated flight deals from Milwaukee to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated mayo 28, 2026.
This Southwest deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/35:00 am
MKE
- MCO
Nonstop2h 40m
Southwest
mar. 7/78:50 pm
MCO
- MKE
Nonstop3h 00m
Southwest
Deal found 5/24![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/1410:11 am
MKE
- MCO
1 stop5h 29m
Delta
mar. 7/214:05 pm
MCO
- MKE
1 stop5h 15m
Delta
Deal found 5/27![Delta logo]()
$267
This United Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/161:19 pm
MKE
- MCO
1 stop5h 13m
United Airlines
sáb. 8/227:40 am
MCO
- MKE
1 stop5h 58m
United Airlines
Deal found 5/26![United Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/303:40 pm
MKE
- MCO
1 stop4h 25m
Southwest
mar. 7/78:50 pm
MCO
- MKE
Nonstop3h 00m
Southwest
Deal found 5/26![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/233:00 pm
MKE
- MCO
1 stop6h 51m
Delta
sáb. 6/275:30 am
MCO
- MKE
1 stop4h 48m
Delta
Deal found 5/23![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/66:25 am
MKE
- MCO
1 stop6h 45m
Southwest
mar. 8/112:05 pm
MCO
- MKE
1 stop8h 20m
Southwest
Deal found 5/26![Southwest logo]()
$279
This Southwest deal was found by Cheapflights users on 5/23. 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.
mié. 6/246:45 am
MKE
- MCO
2 stops6h 55m
Southwest
mié. 7/16:10 am
MCO
- MKE
1 stop4h 35m
Southwest
Deal found 5/23![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/274:00 pm
MKE
- MCO
1 stop6h 10m
Southwest
sáb. 7/412:50 pm
MCO
- MKE
Nonstop2h 45m
Southwest
Deal found 5/27![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 5/23. 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.
vie. 6/198:15 pm
MKE
- MCO
Nonstop2h 50m
Southwest
mié. 6/246:10 am
MCO
- MKE
1 stop4h 35m
Southwest
Deal found 5/23![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/257:30 am
MKE
- MCO
Nonstop2h 40m
Southwest
jue. 6/258:45 pm
MCO
- MKE
1 stop4h 30m
Southwest
Deal found 5/27![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/64:20 pm
MKE
- MCO
1 stop6h 00m
Southwest
lun. 8/107:05 am
MCO
- MKE
Nonstop2h 50m
Southwest
Deal found 5/24![Southwest logo]()
$327
Last-minute flights from Milwaukee to KissimmeeDiscover last-minute flight deals from Milwaukee to Kissimmee. Data last updated mayo 28, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Kissimmee. Data last updated mayo 28, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/168:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
mié. 6/245:25 am
MCO
- MKE
1 stop6h 48m
Frontier
Deal found 5/26![Frontier logo]()
$217
This Trip.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/168:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
mar. 6/236:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 5/26![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/168:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
jue. 6/256:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 5/26![Frontier logo]()
$226
This Priceline deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/1712:08 pm
MKE
- MCO
1 stop5h 23m
Frontier
mié. 6/245:25 am
MCO
- MKE
1 stop6h 48m
Frontier
Deal found 5/26![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/2412:08 pm
MKE
- MCO
1 stop5h 23m
Frontier
mar. 7/76:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 5/25![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/2412:08 pm
MKE
- MCO
1 stop5h 23m
Frontier
mié. 7/15:25 am
MCO
- MKE
1 stop6h 48m
Frontier
Deal found 5/26![Frontier logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/258:53 am
MKE
- MCO
Nonstop2h 51m
Frontier
mar. 7/76:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 5/25![Frontier logo]()
$222
This Expedia deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/2612:08 pm
MKE
- MCO
1 stop9h 01m
Frontier
mar. 7/76:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 5/26![Frontier logo]()
$231
This Super.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/308:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
mar. 7/76:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 5/26![Frontier logo]()
$183
One-way flights from Milwaukee to KissimmeeSearch for one-way flight options from Milwaukee to Kissimmee. Find affordable one-way fares based on user searches. Data last updated mayo 28, 2026.
Search for one-way flight options from Milwaukee to Kissimmee. Find affordable one-way fares based on user searches. Data last updated mayo 28, 2026.
This Frontier deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/258:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
Deal found 5/27![Frontier logo]()
$85
This Super.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/308:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
Deal found 5/27![Frontier logo]()
$89
This Frontier deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/188:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
Deal found 5/25![Frontier logo]()
$94
This Frontier deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/148:43 am
MKE
- MCO
Nonstop2h 53m
Frontier
Deal found 5/26![Frontier logo]()
$96
This Super.com deal was found by Cheapflights users on 5/23. 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.
mar. 6/168:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
Deal found 5/23![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/218:43 am
MKE
- MCO
Nonstop2h 53m
Frontier
Deal found 5/28![Frontier logo]()
$104
This Super.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/112:08 pm
MKE
- MCO
1 stop5h 23m
Frontier
Deal found 5/26![Frontier logo]()
$114
This Frontier deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/2412:08 pm
MKE
- MCO
1 stop5h 23m
Frontier
Deal found 5/27![Frontier logo]()
$115
This Super.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/208:43 am
MKE
- MCO
Nonstop2h 51m
Frontier
Deal found 5/24![Frontier logo]()
$116
This American Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/1911:29 am
MKE
- MCO
1 stop4h 36m
American Airlines
Deal found 5/26![American Airlines logo]()
$119
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/197:11 am
MKE
- MCO
1 stop6h 48m
Delta
Deal found 5/25![Delta logo]()
$120
Find flight deals from Milwaukee to Kissimmee
Keep the following information in mind while searching for Milwaukee to Kissimmee flight deals. Data was last updated mayo 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Kiwi.com) |
One-way from | $85 (Frontier) |
Popular in | April |
Cheapest in | January |
Average price | $345 |
Cheapflights Fare Finder
Customize your flight search to find flights from Milwaukee to Kissimmee 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 mayo 28, 2026.
Use the filters below to find and compare flights from Milwaukee to Kissimmee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
vie. 7/3
5:00 am-8:40 am
Nonstop2h 40m
Orlando
mar. 7/7
8:50 pm-10:50 pm
Nonstop3h 00m
$252
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
mar. 6/30
3:40 pm-9:05 pm
1 stop4h 25m
Orlando
mar. 7/7
8:50 pm-10:50 pm
Nonstop3h 00m
$262
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
mar. 7/14
10:11 am-4:40 pm
1 stop5h 29m
Orlando
mar. 7/21
4:05 pm-8:20 pm
1 stop5h 15m
$267
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
jue. 8/6
6:25 am-2:10 pm
1 stop6h 45m
Orlando
mar. 8/11
2:05 pm-9:25 pm
1 stop8h 20m
$279
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
mié. 6/24
6:45 am-2:40 pm
2 stops6h 55m
Orlando
mié. 7/1
6:10 am-9:45 am
1 stop4h 35m
$282
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
sáb. 6/27
4:00 pm-11:10 pm
1 stop6h 10m
Orlando
sáb. 7/4
12:50 pm-2:35 pm
Nonstop2h 45m
$292
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
vie. 6/19
8:15 pm-12:05 am
Nonstop2h 50m
Orlando
mié. 6/24
6:10 am-9:45 am
1 stop4h 35m
$292
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
mar. 6/23
3:00 pm-10:51 pm
1 stop6h 51m
Orlando
sáb. 6/27
5:30 am-9:18 am
1 stop4h 48m
$302
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
jue. 6/25
7:30 am-11:10 am
Nonstop2h 40m
Orlando
jue. 6/25
8:45 pm-12:15 am
1 stop4h 30m
$327
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
jue. 8/6
4:20 pm-11:20 pm
1 stop6h 00m
Orlando
lun. 8/10
7:05 am-8:55 am
Nonstop2h 50m
$327
Showing 1-10 of 22 resultsSorted by cheapest first
Best time to book a flight from Milwaukee to Kissimmee
Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Milwaukee with our price prediction graph.
MKE-MCO
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 Milwaukee to Kissimmee
MKE-K1S
MKE-MCO
What is the cheapest time of day to fly from MKE to K1S?
Find hourly flight availability from Milwaukee to Kissimmee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated mayo 28, 2026.
It’s typically best to fly out from Milwaukee to Kissimmee in the afternoon. Doing so could potentially save you 22% on the flight price compared to flying in the morning, which is usually more expensive.
How much does it cost to fly round-trip from Milwaukee to Kissimmee?
What is the cheapest day to fly from Milwaukee to Kissimmee?
Use this chart to determine the cheapest time to fly round-trip from Milwaukee to Kissimmee. Price data was last updated on May 23, 2026.
Travelers seeking maximum savings on their Milwaukee to Kissimmee flight should consider departing on Monday evenings when fares are most often at their lowest. Wednesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Kissimmee
Get insights into the airlines that provide service to Kissimmee. 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 Kissimmee. Reviews last updated mayo 28, 2026.
Read reviews from past customers who have flown Southwest,Delta, andAmerican Airlines from Milwaukee to Kissimmee. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Spirit Airlines
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Kissimmee. 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 Milwaukee to Kissimmee
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Complete your trip
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Milwaukee and Kissimmee flights
Browse other Milwaukee and Kissimmee flight options. Last updated on mayo 28, 2026.
Other flights from Milwaukee
Browse through other flights departing from Milwaukee. Flights are based on user searches made on Cheapflights and were last updated on mayo 28, 2026.
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Milwaukee to Kissimmee flights
Consider these flights traveling from Milwaukee to Kissimmee.
Top 7 airlines flying from Milwaukee to Kissimmee
Discover the top 7 airlines that operate flights from Milwaukee to Kissimmee. 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 mayo 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$83 | Average$242 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$86 | Average$217 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$114 | Average$272 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$150 | Average$443 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$437 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$189 | Average$471 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$251 | Average$449 | FlexibilityNo cancel fee | On-time63% |