$78+ 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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MCO
May 11 — May 181
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 July, 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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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 April 11, 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 April 11, 2026.
This Super.com deal was found by Cheapflights users on 4/7. 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 5/59:56 am
MKE
- MCO
Nonstop2h 49m
Frontier
Tue 5/127:00 am
MCO
- MKE
Nonstop3h 01m
Frontier
Deal found 4/7![Frontier logo]()
$146
This Mytrip deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:50 pm
MKE
- MCO
Nonstop2h 47m
Multiple Airlines
Sun 5/107:00 am
MCO
- MKE
Nonstop3h 01m
Multiple Airlines
Deal found 4/11![Multiple Airlines logo]()
$147
This Frontier deal was found by Cheapflights users on 4/8. 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 5/199:56 am
MKE
- MCO
Nonstop2h 49m
Frontier
Tue 6/26:00 am
MCO
- MKE
Nonstop3h 01m
Frontier
Deal found 4/8![Frontier logo]()
$148
This Frontier deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:09 pm
MKE
- MCO
1 stop6h 23m
Frontier
Tue 6/96:00 am
MCO
- MKE
Nonstop2h 58m
Frontier
Deal found 4/10![Frontier logo]()
$149
This Frontier deal was found by Cheapflights users on 4/8. 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 4/3012:21 pm
MKE
- MCO
Nonstop2h 55m
Frontier
Thu 5/77:00 am
MCO
- MKE
Nonstop3h 01m
Frontier
Deal found 4/8![Frontier logo]()
$150
This Super.com deal was found by Cheapflights users on 4/6. 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 4/3012:21 pm
MKE
- MCO
Nonstop2h 55m
Frontier
Mon 5/49:18 am
MCO
- MKE
Nonstop3h 08m
Frontier
Deal found 4/6![Frontier logo]()
$152
This Frontier deal was found by Cheapflights users on 4/6. 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 4/3012:21 pm
MKE
- MCO
Nonstop2h 55m
Frontier
Tue 5/57:00 am
MCO
- MKE
Nonstop3h 01m
Frontier
Deal found 4/6![Frontier logo]()
$153
This Frontier deal was found by Cheapflights users on 4/8. 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 4/275:05 pm
MKE
- MCO
1 stop11h 38m
Frontier
Tue 5/57:00 am
MCO
- MKE
Nonstop3h 01m
Frontier
Deal found 4/8![Frontier logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 4/10. 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 5/612:09 pm
MKE
- MCO
1 stop8h 38m
Frontier
Thu 5/147:00 am
MCO
- MKE
Nonstop3h 01m
Frontier
Deal found 4/10![Frontier logo]()
$157
This Frontier deal was found by Cheapflights users on 4/8. 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 4/3012:21 pm
MKE
- MCO
Nonstop2h 55m
Frontier
Sun 5/36:30 am
MCO
- MKE
Nonstop3h 08m
Frontier
Deal found 4/8![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 6/48:46 am
MKE
- MCO
Nonstop2h 49m
Frontier
Sun 6/76:00 am
MCO
- MKE
Nonstop3h 01m
Frontier
Deal found 4/6![Frontier logo]()
$163
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 April 11, 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 April 11, 2026.
This Southwest deal was found by Cheapflights users on 4/10. 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 5/283:30 pm
MKE
- MCO
1 stop7h 35m
Southwest
Tue 6/28:55 pm
MCO
- MKE
Nonstop2h 55m
Southwest
Deal found 4/10![Southwest logo]()
$264
This United Airlines deal was found by Cheapflights users on 4/6. 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.
Thu 5/286:14 am
MKE
- MCO
1 stop6h 49m
United Airlines
Sun 5/317:13 am
MCO
- MKE
1 stop5h 01m
United Airlines
Deal found 4/6![United Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 4/6. 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 4/307:50 pm
MKE
- MCO
Nonstop2h 40m
Southwest
Tue 5/53:35 pm
MCO
- MKE
1 stop7h 40m
Southwest
Deal found 4/6![Southwest logo]()
$264
This Southwest deal was found by Cheapflights users on 4/8. 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 4/303:30 pm
MKE
- MCO
1 stop6h 40m
Southwest
Wed 5/610:20 am
MCO
- MKE
2 stops6h 55m
Southwest
Deal found 4/8![Southwest logo]()
$323
This United Airlines deal was found by Cheapflights users on 4/6. 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.
Mon 5/256:05 am
MKE
- MCO
2 stops7h 38m
United Airlines
Sat 5/307:13 am
MCO
- MKE
1 stop6h 35m
United Airlines
Deal found 4/6![United Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 4/6. 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 4/2612:10 pm
MKE
- MCO
1 stop6h 54m
United Airlines
Tue 4/284:53 pm
MCO
- MKE
1 stop4h 55m
United Airlines
Deal found 4/6![United Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 4/6. 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 6/244:20 pm
MKE
- MCO
Nonstop2h 50m
Southwest
Thu 6/2510:15 pm
MCO
- MKE
Nonstop2h 50m
Southwest
Deal found 4/6![Southwest logo]()
$354
This United Airlines deal was found by Cheapflights users on 4/10. 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.
Fri 5/151:46 pm
MKE
- MCO
2 stops10h 13m
United Airlines
Mon 5/186:10 pm
MCO
- MKE
1 stop6h 49m
United Airlines
Deal found 4/10![United Airlines logo]()
$396
This Southwest deal was found by Cheapflights users on 4/9. 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 6/272:45 pm
MKE
- MCO
1 stop6h 45m
Southwest
Wed 7/16:20 am
MCO
- MKE
1 stop4h 15m
Southwest
Deal found 4/9![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 4/8. 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 4/303:30 pm
MKE
- MCO
1 stop6h 40m
Southwest
Mon 5/45:45 pm
MCO
- MKE
2 stops6h 40m
Southwest
Deal found 4/8![Southwest logo]()
$384
This Southwest deal was found by Cheapflights users on 4/10. 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 5/83:20 pm
MKE
- MCO
Nonstop2h 40m
Southwest
Mon 5/118:55 pm
MCO
- MKE
Nonstop2h 55m
Southwest
Deal found 4/10![Southwest logo]()
$393
Last-minute flights from Milwaukee to KissimmeeDiscover last-minute flight deals from Milwaukee to Kissimmee. Data last updated April 11, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Kissimmee. Data last updated April 11, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/9. 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 4/177:34 pm
MKE
- MCO
Nonstop3h 04m
Frontier
Fri 4/249:00 am
MCO
- MKE
1 stop8h 28m
Frontier
Deal found 4/9![Frontier logo]()
$164
This Frontier deal was found by Cheapflights users on 4/8. 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 4/275:05 pm
MKE
- MCO
1 stop11h 38m
Frontier
Tue 5/57:00 am
MCO
- MKE
Nonstop3h 01m
Frontier
Deal found 4/8![Frontier logo]()
$154
This Frontier deal was found by Cheapflights users on 4/8. 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 4/3012:21 pm
MKE
- MCO
Nonstop2h 55m
Frontier
Thu 5/77:00 am
MCO
- MKE
Nonstop3h 01m
Frontier
Deal found 4/8![Frontier logo]()
$150
This Super.com deal was found by Cheapflights users on 4/6. 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 4/3012:21 pm
MKE
- MCO
Nonstop2h 55m
Frontier
Mon 5/49:18 am
MCO
- MKE
Nonstop3h 08m
Frontier
Deal found 4/6![Frontier logo]()
$152
This Frontier deal was found by Cheapflights users on 4/6. 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 4/3012:21 pm
MKE
- MCO
Nonstop2h 55m
Frontier
Tue 5/57:00 am
MCO
- MKE
Nonstop3h 01m
Frontier
Deal found 4/6![Frontier logo]()
$153
This Frontier deal was found by Cheapflights users on 4/8. 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 4/3012:21 pm
MKE
- MCO
Nonstop2h 55m
Frontier
Sun 5/36:30 am
MCO
- MKE
Nonstop3h 08m
Frontier
Deal found 4/8![Frontier logo]()
$160
This Super.com deal was found by Cheapflights users on 4/9. 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.
Mon 5/412:21 pm
MKE
- MCO
Nonstop2h 55m
Frontier
Sun 5/107:00 am
MCO
- MKE
Nonstop3h 01m
Frontier
Deal found 4/9![Frontier logo]()
$163
This Super.com deal was found by Cheapflights users on 4/7. 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 5/59:56 am
MKE
- MCO
Nonstop2h 49m
Frontier
Tue 5/127:00 am
MCO
- MKE
Nonstop3h 01m
Frontier
Deal found 4/7![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 4/10. 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 5/612:09 pm
MKE
- MCO
1 stop8h 38m
Frontier
Thu 5/147:00 am
MCO
- MKE
Nonstop3h 01m
Frontier
Deal found 4/10![Frontier logo]()
$157
This Mytrip deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:50 pm
MKE
- MCO
Nonstop2h 47m
Multiple Airlines
Sun 5/107:00 am
MCO
- MKE
Nonstop3h 01m
Multiple Airlines
Deal found 4/11![Multiple Airlines logo]()
$147
This Frontier deal was found by Cheapflights users on 4/8. 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 5/199:56 am
MKE
- MCO
Nonstop2h 49m
Frontier
Tue 6/26:00 am
MCO
- MKE
Nonstop3h 01m
Frontier
Deal found 4/8![Frontier logo]()
$148
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 April 11, 2026.
Search for one-way flight options from Milwaukee to Kissimmee. Find affordable one-way fares based on user searches. Data last updated April 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 5/32:50 pm
MKE
- MCO
Nonstop2h 47m
Sun Country Air
Deal found 4/6![Sun Country Air logo]()
$78
This Frontier deal was found by Cheapflights users on 4/6. 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 5/1112:09 pm
MKE
- MCO
1 stop6h 23m
Frontier
Deal found 4/6![Frontier logo]()
$80
This Frontier deal was found by Cheapflights users on 4/6. 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 4/275:05 pm
MKE
- MCO
1 stop11h 38m
Frontier
Deal found 4/6![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 5/72:50 pm
MKE
- MCO
Nonstop2h 47m
Sun Country Air
Deal found 4/6![Sun Country Air logo]()
$88
This Cheapflightsfares deal was found by Cheapflights users on 4/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:50 pm
MKE
- MCO
Nonstop2h 47m
Sun Country Air
Deal found 4/7![Sun Country Air logo]()
$89
This Super.com deal was found by Cheapflights users on 4/8. 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 5/248:46 am
MKE
- MCO
Nonstop2h 49m
Frontier
Deal found 4/8![Frontier logo]()
$90
This eDestinos deal was found by Cheapflights users on 4/7. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:09 pm
MKE
- MCO
1 stop6h 23m
Frontier
Deal found 4/7![Frontier logo]()
$91
This Super.com deal was found by Cheapflights users on 4/7. 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 5/2012:09 pm
MKE
- MCO
1 stop6h 23m
Frontier
Deal found 4/7![Frontier logo]()
$99
This Frontier deal was found by Cheapflights users on 4/7. 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.
Sat 6/612:29 pm
MKE
- MCO
1 stop5h 33m
Frontier
Deal found 4/7![Frontier logo]()
$100
This Super.com deal was found by Cheapflights users on 4/6. 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.
Fri 5/1512:09 pm
MKE
- MCO
1 stop8h 38m
Frontier
Deal found 4/6![Frontier logo]()
$104
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 April 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $146 (Super.com) |
One-way from | $78 (Kiwi.com) |
Popular in | April |
Cheapest in | January |
Average price | $389 |
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 April 11, 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 5/28
3:30 pm-12:05 am
1 stop7h 35m
Orlando
Tue 6/2
8:55 pm-10:50 pm
Nonstop2h 55m
$264
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Thu 4/30
7:50 pm-11:30 pm
Nonstop2h 40m
Orlando
Tue 5/5
3:35 pm-10:15 pm
1 stop7h 40m
$264
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Thu 4/30
3:30 pm-11:10 pm
1 stop6h 40m
Orlando
Wed 5/6
10:20 am-4:15 pm
2 stops6h 55m
$323
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Thu 5/28
6:14 am-2:03 pm
1 stop6h 49m
Orlando
Sun 5/31
7:13 am-11:14 am
1 stop5h 01m
$342
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Wed 6/24
4:20 pm-8:10 pm
Nonstop2h 50m
Orlando
Thu 6/25
10:15 pm-12:05 am
Nonstop2h 50m
$354
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Sat 6/27
2:45 pm-10:30 pm
1 stop6h 45m
Orlando
Wed 7/1
6:20 am-9:35 am
1 stop4h 15m
$364
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Mon 5/25
6:05 am-2:43 pm
2 stops7h 38m
Orlando
Sat 5/30
7:13 am-12:48 pm
1 stop6h 35m
$369
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Thu 4/30
3:30 pm-11:10 pm
1 stop6h 40m
Orlando
Mon 5/4
5:45 pm-11:25 pm
2 stops6h 40m
$384
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Sun 4/26
12:10 pm-8:04 pm
1 stop6h 54m
Orlando
Tue 4/28
4:53 pm-8:48 pm
1 stop4h 55m
$385
Quickest round-trip
MilwaukeeOrlando
MKE - MCO
MKEMCO
Milwaukee-Mitchell
Fri 5/8
3:20 pm-7:00 pm
Nonstop2h 40m
Orlando
Mon 5/11
8:55 pm-10:50 pm
Nonstop2h 55m
$393
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
How far ahead should I book a flight from Milwaukee to Kissimmee?
Use this chart to determine the optimal time to book a round-trip flight from Milwaukee to Kissimmee. Price data was last updated on April 9, 2026.
To ensure you get the cheapest price possible for a flight from Milwaukee to Kissimmee, you should look to book at least 83 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Milwaukee to Kissimmee?
Currently, January is the cheapest month in which you can book a flight from Milwaukee to Kissimmee (average of $58). Flying from Milwaukee to Kissimmee in June is currently the most expensive (average of $108). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 April 11, 2026.
It’s typically best to fly out from Milwaukee to Kissimmee in the afternoon. Doing so could potentially save you 21% on the flight price compared to flying in the morning, which is usually more expensive.
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 April 11, 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.
How much does it cost to fly round-trip from Milwaukee to Kissimmee?
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 April 11, 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.
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
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
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
Find flights from Milwaukee to Kissimmee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Milwaukee and Kissimmee flights
Browse other Milwaukee and Kissimmee flight options. Last updated on April 11, 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 April 11, 2026.
Popular flight searches
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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 April 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$83 | Average$252 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$200 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$114 | Average$274 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$150 | Average$403 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$436 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$189 | Average$464 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$252 | Average$446 | FlexibilityNo cancel fee | On-time63% |