$115+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MCO
Aug 23 — Aug 301
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
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 Milwaukee-Mitchell to Kissimmee are usually found in January or August, booked 62 days in advance, depart on a Tuesday or Thursday and return on a Wednesday
Cheap flight deals from Milwaukee to Kissimmee
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Best
Last-minute
One-way
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 July 24, 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 July 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Thu 9/248:10 pm
MKE
- MCO
Nonstop2h 47m
Frontier
Thu 10/85:02 pm
MCO
- MKE
Nonstop3h 13m
Frontier
Deal found 7/20![Frontier logo]()
$177
This Frontier deal was found by Cheapflights users on 7/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:10 pm
MKE
- MCO
Nonstop2h 47m
Frontier
Mon 10/125:02 pm
MCO
- MKE
Nonstop3h 13m
Frontier
Deal found 7/23![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:10 pm
MKE
- MCO
Nonstop2h 47m
Frontier
Fri 10/304:56 pm
MCO
- MKE
Nonstop3h 12m
Frontier
Deal found 7/19![Frontier logo]()
$179
This Super.com deal was found by Cheapflights users on 7/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/612:10 pm
MKE
- MCO
Nonstop2h 48m
Frontier
Fri 9/115:02 pm
MCO
- MKE
Nonstop3h 13m
Frontier
Deal found 7/19![Frontier logo]()
$185
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:10 pm
MKE
- MCO
Nonstop2h 48m
Frontier
Thu 8/209:15 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 7/21![Frontier logo]()
$187
This Frontier deal was found by Cheapflights users on 7/22. 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.
Thu 10/298:03 pm
MKE
- MCO
Nonstop2h 47m
Frontier
Mon 11/24:56 pm
MCO
- MKE
Nonstop3h 12m
Frontier
Deal found 7/22![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/128:10 pm
MKE
- MCO
Nonstop2h 47m
Frontier
Mon 10/195:02 pm
MCO
- MKE
Nonstop3h 13m
Frontier
Deal found 7/19![Frontier logo]()
$192
This Frontier deal was found by Cheapflights users on 7/22. 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 9/118:10 pm
MKE
- MCO
Nonstop2h 47m
Frontier
Mon 9/215:02 pm
MCO
- MKE
Nonstop3h 13m
Frontier
Deal found 7/22![Frontier logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:10 pm
MKE
- MCO
Nonstop2h 47m
Frontier
Sat 10/175:02 pm
MCO
- MKE
Nonstop3h 13m
Frontier
Deal found 7/19![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Thu 10/158:10 pm
MKE
- MCO
Nonstop2h 47m
Frontier
Sat 10/175:02 pm
MCO
- MKE
Nonstop3h 13m
Frontier
Deal found 7/23![Frontier logo]()
$201
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:10 pm
MKE
- MCO
Nonstop2h 48m
Frontier
Sun 8/239:15 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 7/21![Frontier logo]()
$202
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 July 24, 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 July 24, 2026.
This Southwest deal was found by Cheapflights users on 7/23. 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.
Thu 11/512:45 pm
MKE
- MCO
1 stop5h 40m
Southwest
Tue 11/106:45 pm
MCO
- MKE
1 stop4h 25m
Southwest
Deal found 7/23![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 7/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/281:28 pm
MKE
- MCO
1 stop6h 45m
Delta
Mon 10/53:40 pm
MCO
- MKE
1 stop7h 09m
Delta
Deal found 7/19![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/224:25 pm
MKE
- MCO
Nonstop2h 45m
Southwest
Sat 8/291:20 pm
MCO
- MKE
Nonstop2h 50m
Southwest
Deal found 7/22![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 7/23. 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.
Tue 11/38:10 am
MKE
- MCO
1 stop5h 00m
Southwest
Tue 11/103:20 pm
MCO
- MKE
Nonstop3h 00m
Southwest
Deal found 7/23![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 7/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:30 pm
MKE
- MCO
1 stop7h 39m
Delta
Wed 11/115:30 am
MCO
- MKE
1 stop4h 52m
Delta
Deal found 7/19![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 7/22. 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 10/127:20 am
MKE
- MCO
1 stop6h 45m
Southwest
Thu 10/154:00 pm
MCO
- MKE
Nonstop2h 50m
Southwest
Deal found 7/22![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 7/22. 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 8/197:50 am
MKE
- MCO
1 stop7h 25m
Southwest
Wed 8/269:00 am
MCO
- MKE
Nonstop2h 55m
Southwest
Deal found 7/22![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 7/23. 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.
Sat 9/125:45 am
MKE
- MCO
2 stops5h 50m
Southwest
Sat 9/191:20 pm
MCO
- MKE
Nonstop2h 50m
Southwest
Deal found 7/23![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 7/21. 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.
Tue 9/297:40 am
MKE
- MCO
2 stops5h 55m
Southwest
Sat 10/36:25 am
MCO
- MKE
1 stop6h 55m
Southwest
Deal found 7/21![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 7/21. 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.
Thu 9/2411:35 am
MKE
- MCO
2 stops5h 30m
Southwest
Mon 9/286:10 am
MCO
- MKE
1 stop4h 25m
Southwest
Deal found 7/21![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 7/19. 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.
Mon 10/125:00 pm
MKE
- MCO
1 stop6h 10m
Southwest
Mon 10/199:10 am
MCO
- MKE
1 stop8h 15m
Southwest
Deal found 7/19![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 7/20. 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.
Tue 8/257:40 am
MKE
- MCO
2 stops5h 55m
Southwest
Thu 8/2710:15 am
MCO
- MKE
2 stops6h 45m
Southwest
Deal found 7/20![Southwest logo]()
$335
Last-minute flights from Milwaukee to KissimmeeDiscover last-minute flight deals from Milwaukee to Kissimmee. Data last updated July 24, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Kissimmee. Data last updated July 24, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 7/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:43 am
MKE
- MCO
Nonstop2h 53m
Frontier
Tue 8/116:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 7/21![Frontier logo]()
$248
This Super.com deal was found by Cheapflights users on 7/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/98:43 am
MKE
- MCO
Nonstop2h 48m
Frontier
Tue 8/116:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 7/20![Frontier logo]()
$216
This Frontier deal was found by Cheapflights users on 7/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:43 am
MKE
- MCO
Nonstop2h 48m
Frontier
Tue 8/189:15 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 7/19![Frontier logo]()
$218
This Super.com deal was found by Cheapflights users on 7/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:43 am
MKE
- MCO
Nonstop2h 48m
Frontier
Sun 8/166:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 7/20![Frontier logo]()
$212
This Super.com deal was found by Cheapflights users on 7/23. 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.
Tue 8/1812:10 pm
MKE
- MCO
Nonstop2h 48m
Frontier
Tue 8/259:15 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 7/23![Frontier logo]()
$187
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:10 pm
MKE
- MCO
Nonstop2h 48m
Frontier
Sun 8/239:15 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 7/21![Frontier logo]()
$202
This Frontier deal was found by Cheapflights users on 7/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:10 pm
MKE
- MCO
Nonstop2h 48m
Frontier
Sun 8/309:15 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 7/21![Frontier logo]()
$203
This Southwest deal was found by Cheapflights users on 7/23. 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.
Tue 8/183:05 pm
MKE
- MCO
1 stop5h 00m
Southwest
Tue 8/252:25 pm
MCO
- MKE
Nonstop2h 55m
Southwest
Deal found 7/23![Southwest logo]()
$247
This Frontier deal was found by Cheapflights users on 7/22. 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.
Thu 8/2012:10 pm
MKE
- MCO
Nonstop2h 48m
Frontier
Thu 8/279:15 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 7/22![Frontier logo]()
$188
This Southwest deal was found by Cheapflights users on 7/23. 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.
Thu 8/271:55 pm
MKE
- MCO
Nonstop2h 45m
Southwest
Sat 8/298:05 am
MCO
- MKE
Nonstop2h 50m
Southwest
Deal found 7/23![Southwest logo]()
$237
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 July 24, 2026.
Search for one-way flight options from Milwaukee to Kissimmee. Find affordable one-way fares based on user searches. Data last updated July 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Sun 10/118:10 pm
MKE
- MCO
Nonstop2h 47m
Frontier
Deal found 7/23![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Sun 10/188:10 pm
MKE
- MCO
Nonstop2h 47m
Frontier
Deal found 7/23![Frontier logo]()
$117
This Southwest deal was found by Cheapflights users on 7/23. 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.
Wed 8/196:05 am
MKE
- MCO
Nonstop2h 40m
Southwest
Deal found 7/23![Southwest logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Thu 10/228:10 pm
MKE
- MCO
Nonstop2h 47m
Frontier
Deal found 7/20![Frontier logo]()
$123
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:43 am
MKE
- MCO
Nonstop2h 48m
Frontier
Deal found 7/21![Frontier logo]()
$125
This Southwest deal was found by Cheapflights users on 7/23. 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.
Sat 8/221:15 pm
MKE
- MCO
Nonstop2h 45m
Southwest
Deal found 7/23![Southwest logo]()
$139
This Southwest deal was found by Cheapflights users on 7/20. 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.
Tue 8/2510:00 am
MKE
- MCO
1 stop5h 35m
Southwest
Deal found 7/20![Southwest logo]()
$144
This Delta deal was found by Cheapflights users on 7/23. 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.
Sat 10/241:15 pm
MKE
- MCO
1 stop5h 06m
Delta
Deal found 7/23![Delta logo]()
$149
This Super.com deal was found by Cheapflights users on 7/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:43 am
MKE
- MCO
Nonstop2h 53m
Frontier
Deal found 7/19![Frontier logo]()
$152
This Delta deal was found by Cheapflights users on 7/22. 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 8/2212:47 pm
MKE
- MCO
1 stop6h 48m
Delta
Deal found 7/22![Delta logo]()
$154
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 July 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Kiwi.com) |
One-way from | $115 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $373 |
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 July 24, 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
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Thu 11/5
12:45 pm-7:25 pm
1 stop5h 40m
Orlando
Tue 11/10
6:45 pm-10:10 pm
1 stop4h 25m
$257
Quickest round-trip
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Sat 8/22
4:25 pm-8:10 pm
Nonstop2h 45m
Orlando
Sat 8/29
1:20 pm-3:10 pm
Nonstop2h 50m
$277
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Tue 11/3
8:10 am-2:10 pm
1 stop5h 00m
Orlando
Tue 11/10
3:20 pm-5:20 pm
Nonstop3h 00m
$283
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Mon 10/12
7:20 am-3:05 pm
1 stop6h 45m
Orlando
Thu 10/15
4:00 pm-5:50 pm
Nonstop2h 50m
$287
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Wed 8/19
7:50 am-4:15 pm
1 stop7h 25m
Orlando
Wed 8/26
9:00 am-10:55 am
Nonstop2h 55m
$287
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Sat 9/12
5:45 am-12:35 pm
2 stops5h 50m
Orlando
Sat 9/19
1:20 pm-3:10 pm
Nonstop2h 50m
$292
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Tue 9/29
7:40 am-2:35 pm
2 stops5h 55m
Orlando
Sat 10/3
6:25 am-12:20 pm
1 stop6h 55m
$302
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Thu 9/24
11:35 am-6:05 pm
2 stops5h 30m
Orlando
Mon 9/28
6:10 am-9:35 am
1 stop4h 25m
$318
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Mon 9/28
1:28 pm-9:13 pm
1 stop6h 45m
Orlando
Mon 10/5
3:40 pm-9:49 pm
1 stop7h 09m
$329
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Sat 11/7
3:30 pm-12:09 am
1 stop7h 39m
Orlando
Wed 11/11
5:30 am-9:22 am
1 stop4h 52m
$329
Showing 1-10 of 23 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 July 24, 2026.
It’s typically best to fly out from Milwaukee to Kissimmee in the afternoon. Doing so could potentially save you 20% 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?
Airfare is below average for this route at the moment.
Milwaukee to Kissimmee flights typically cost between $214 and $444 in August.The cheapest round-trip price found within the last 5 days was $177 on Frontier (Aug 25-Aug 27).
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 July 18, 2026.
Travelers seeking maximum savings on their Milwaukee to Kissimmee flight should consider departing on Sunday evenings when fares are most often at their lowest. Friday at noon 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 July 24, 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.
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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
Complete your trip to Kissimmee by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Milwaukee to Kissimmee by cabin class
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Milwaukee and Kissimmee flights
Browse other Milwaukee and Kissimmee flight options. Last updated on July 24, 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 July 24, 2026.
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Milwaukee to Kissimmee flights
Consider these flights traveling from Milwaukee to Kissimmee.
Top 6 airlines flying from Milwaukee to Kissimmee
Discover the top 6 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 July 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$83 | Average$241 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$116 | Average$277 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$131 | Average$474 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$150 | Average$428 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$436 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$254 | Average$451 | FlexibilityNo cancel fee | On-time63% |