$64+ Cheap flights from Milwaukee (MKE) to Kissimmee, FL
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MCO
Oct 11 — Oct 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 February, booked 22 days in advance, depart on a Tuesday or Thursday and return on a Wednesday
Cheap flight deals from Milwaukee to Kissimmee
Cheapest
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 September 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 September 11, 2026.
This Frontier deal was found by Cheapflights users on 9/9. 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 12/115:33 pm -
Nonstop2h 58m
Sun 12/132:26 pm -
Nonstop3h 12m
Deal found 9/9![Frontier logo]()
$168
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:15 am -
Nonstop2h 51m
Sun 11/17:06 am -
Nonstop3h 10m
Deal found 9/8![Frontier logo]()
$173
This Frontier deal was found by Cheapflights users on 9/10. 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.
Sun 12/65:33 pm -
Nonstop2h 58m
Thu 12/102:26 pm -
Nonstop3h 12m
Deal found 9/10![Frontier logo]()
$174
This Priceline deal was found by Cheapflights users on 9/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/810:15 am -
Nonstop2h 48m
Tue 10/137:06 am -
Nonstop3h 14m
Deal found 9/6![Frontier logo]()
$177
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:15 am -
Nonstop2h 51m
Sun 11/157:06 am -
Nonstop3h 10m
Deal found 9/8![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 11/1210:15 am -
Nonstop2h 51m
Sun 11/157:06 am -
Nonstop3h 10m
Deal found 9/6![Frontier logo]()
$179
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:33 pm -
Nonstop2h 58m
Mon 12/72:26 pm -
Nonstop3h 12m
Deal found 9/10![Frontier logo]()
$181
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/810:15 am -
Nonstop2h 48m
Sun 10/117:06 am -
Nonstop3h 14m
Deal found 9/10![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 9/8. 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 10/2910:15 am -
Nonstop2h 51m
Sun 11/17:06 am -
Nonstop3h 10m
Deal found 9/8![Frontier logo]()
$183
This Priceline deal was found by Cheapflights users on 9/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/286:11 pm -
Nonstop2h 51m
Thu 12/32:26 pm -
Nonstop3h 12m
Deal found 9/9![Frontier logo]()
$185
This deal was found by Cheapflights users on 9/8. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:10 am -
Nonstop2h 50m
Thu 9/177:06 am -
Nonstop3h 02m
Deal found 9/8![Frontier logo]()
$186
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:11 pm -
Nonstop2h 51m
Mon 11/233:17 pm -
Nonstop3h 09m
Deal found 9/8![Frontier logo]()
$194
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 September 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 September 11, 2026.
This Southwest deal was found by Cheapflights users on 9/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/88:05 pm -
Nonstop2h 50m
Tue 10/136:40 am -
1 stop6h 15m
Deal found 9/7![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/1512:05 pm -
1 stop6h 26m
Mon 10/269:22 am -
1 stop5h 10m
Deal found 9/10![United Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 9/8. 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.
Wed 12/23:50 pm -
Nonstop2h 55m
Wed 12/96:35 am -
1 stop8h 30m
Deal found 9/8![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 9/10. 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.
Tue 10/132:20 pm -
1 stop5h 15m
Fri 10/165:05 pm -
2 stops7h 05m
Deal found 9/10![Southwest logo]()
$288
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Sat 10/315:00 am -
1 stop5h 07m
Wed 11/410:54 am -
1 stop5h 04m
Deal found 9/10![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 9/8. 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.
Sat 11/214:45 pm -
1 stop4h 05m
Thu 11/268:40 am -
Nonstop2h 55m
Deal found 9/8![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 9/8. 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 11/52:35 pm -
Nonstop2h 40m
Mon 11/167:05 pm -
Nonstop2h 55m
Deal found 9/8![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 9/9. 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.
Mon 11/235:10 am -
Nonstop3h 00m
Tue 11/249:00 am -
1 stop7h 00m
Deal found 9/9![Southwest logo]()
$374
This Southwest deal was found by Cheapflights users on 9/6. 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.
Sat 12/53:15 pm -
Nonstop2h 40m
Sat 12/125:25 pm -
Nonstop3h 00m
Deal found 9/6![Southwest logo]()
$375
This Southwest deal was found by Cheapflights users on 9/6. 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.
Tue 10/66:55 pm -
Nonstop2h 45m
Tue 10/136:40 am -
1 stop6h 15m
Deal found 9/6![Southwest logo]()
$385
This Southwest deal was found by Cheapflights users on 9/6. 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.
Fri 12/47:45 am -
2 stops6h 05m
Fri 12/117:45 am -
Nonstop2h 55m
Deal found 9/6![Southwest logo]()
$390
This Southwest deal was found by Cheapflights users on 9/8. 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.
Fri 10/95:50 pm -
1 stop4h 30m
Sun 10/116:05 am -
1 stop4h 35m
Deal found 9/8![Southwest logo]()
$394
Last-minute flights from Milwaukee to KissimmeeDiscover last-minute flight deals from Milwaukee to Kissimmee. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Kissimmee. Data last updated September 11, 2026 and is based on user searches.
This deal was found by Cheapflights users on 9/8. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:10 am -
Nonstop2h 50m
Thu 9/177:06 am -
Nonstop3h 02m
Deal found 9/8![Frontier logo]()
$186
This Frontier deal was found by Cheapflights users on 9/6. 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.
Sun 9/2710:10 am -
Nonstop2h 50m
Sun 10/47:20 am -
Nonstop3h 02m
Deal found 9/6![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:10 am -
Nonstop2h 50m
Sun 10/47:20 am -
Nonstop3h 02m
Deal found 9/9![Frontier logo]()
$214
This Frontier deal was found by Cheapflights users on 9/8. 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.
Sun 10/410:10 am -
Nonstop2h 50m
Sun 10/117:06 am -
Nonstop3h 14m
Deal found 9/8![Frontier logo]()
$198
This Priceline deal was found by Cheapflights users on 9/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/810:15 am -
Nonstop2h 48m
Tue 10/137:06 am -
Nonstop3h 14m
Deal found 9/6![Frontier logo]()
$177
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/810:15 am -
Nonstop2h 48m
Sun 10/117:06 am -
Nonstop3h 14m
Deal found 9/10![Frontier logo]()
$182
This Southwest deal was found by Cheapflights users on 9/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/88:05 pm -
Nonstop2h 50m
Mon 10/1210:35 pm -
Nonstop3h 05m
Deal found 9/7![Southwest logo]()
$217
This Frontier deal was found by Cheapflights users on 9/6. 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 10/1510:15 am -
Nonstop2h 48m
Sun 10/187:06 am -
Nonstop3h 14m
Deal found 9/6![Frontier logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/2010:15 am -
Nonstop2h 48m
Tue 10/277:06 am -
Nonstop3h 10m
Deal found 9/5![Frontier logo]()
$196
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:15 am -
Nonstop2h 48m
Sun 10/257:06 am -
Nonstop3h 14m
Deal found 9/8![Frontier logo]()
$213
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:15 am -
Nonstop2h 51m
Sun 11/17:06 am -
Nonstop3h 10m
Deal found 9/8![Frontier logo]()
$173
This Frontier deal was found by Cheapflights users on 9/8. 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 10/2910:15 am -
Nonstop2h 51m
Sun 11/17:06 am -
Nonstop3h 10m
Deal found 9/8![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 September 11, 2026.
Search for one-way flight options from Milwaukee to Kissimmee. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This Super.com deal was found by Cheapflights users on 9/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:15 am -
Nonstop2h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$64
This Frontier deal was found by Cheapflights users on 9/9. 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.
Thu 10/810:15 am -
Nonstop2h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1710:15 am -
Nonstop2h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Fri 11/68:03 pm -
Nonstop2h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$103
This Southwest deal was found by Cheapflights users on 9/10. 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.
Wed 11/117:20 pm -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Southwest logo]()
$109
This Southwest deal was found by Cheapflights users on 9/10. 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.
Mon 11/168:10 am -
1 stop5h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Southwest logo]()
$114
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:15 am -
Nonstop2h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$115
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:11 pm -
Nonstop2h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:33 pm -
Nonstop2h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$122
This Super.com deal was found by Cheapflights users on 9/7. 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.
Thu 10/110:10 am -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$141
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 September 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $168 (Priceline) |
One-way from | $64 (Super.com) |
Popular in | June |
Cheapest in | January |
Average price | $368 |
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 7,457,451 searches. Data last updated September 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 Milwaukee-Mitchell - MCO Orlando
MKEMCO
Milwaukee-Mitchell
Wed 12/9
7:20 pm-11:10 pm
Nonstop2h 50m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
MilwaukeeOrlando
MKE Milwaukee-Mitchell - MCO Orlando
MKEMCO
Milwaukee-Mitchell
Wed 11/11
7:20 pm-11:10 pm
Nonstop2h 50m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
MilwaukeeOrlando
MKE Milwaukee-Mitchell - MCO Orlando
MKEMCO
Milwaukee-Mitchell
Wed 9/30
7:14 am-3:02 pm
1 stop6h 48m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$119
MilwaukeeOrlando
MKE Milwaukee-Mitchell - MCO Orlando
MKEMCO
Milwaukee-Mitchell
Wed 12/9
7:00 am-2:58 pm
1 stop6h 58m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$119
MilwaukeeOrlando
MKE Milwaukee-Mitchell - MCO Orlando
MKEMCO
Milwaukee-Mitchell
Fri 10/2
8:05 pm-11:50 pm
Nonstop2h 45m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$155
MilwaukeeOrlando
MKE Milwaukee-Mitchell - MCO Orlando
MKEMCO
Milwaukee-Mitchell
Fri 11/13
7:50 pm-11:35 pm
Nonstop2h 45m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$155
MilwaukeeOrlando
MKE Milwaukee-Mitchell - MCO Orlando
MKEMCO
Milwaukee-Mitchell
Wed 12/9
7:17 am-6:12 pm
2 stops9h 55m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$169
MilwaukeeOrlando
MKE Milwaukee-Mitchell - MCO Orlando
MKEMCO
Milwaukee-Mitchell
Wed 9/30
2:05 pm-5:50 pm
Nonstop2h 45m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
Quickest round-trip
MilwaukeeOrlando
MKE Milwaukee-Mitchell - MCO Orlando
MKEMCO
Milwaukee-Mitchell
Thu 11/26
10:10 am-1:50 pm
Nonstop2h 40m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
MilwaukeeOrlando
MKE Milwaukee-Mitchell - MCO Orlando
MKEMCO
Milwaukee-Mitchell
Mon 10/19
8:05 pm-11:55 pm
Nonstop2h 50m
Orlando
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
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 September 11, 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 $290 and $423 in December.The cheapest round-trip price found within the last 5 days was $168 on Frontier (Dec 6-Dec 10).
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 September 5, 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 September 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.
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
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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Milwaukee and Kissimmee flights
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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 7,457,451 searches. Data last updated September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$83 | Average$241 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$128 | Average$280 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$131 | Average$477 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$150 | Average$441 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$166 | Average$361 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$176 | Average$393 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$258 | Average$451 | FlexibilityNo cancel fee | On-time63% |