$165+ Cheap flights from Milwaukee (MKE) to Puerto Rico
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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Aug 31 — Sep 71
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee to Puerto Rico with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Milwaukee to Puerto RicoExplore the most affordable flight options available from Milwaukee to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2026.
Explore the most affordable flight options available from Milwaukee to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:10 pm
MKE
- SJU
1 stop13h 05m
Frontier
Mon 8/248:57 pm
SJU
- MKE
1 stop15h 16m
Frontier
Deal found 7/28![Frontier logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 9/312:10 pm
MKE
- SJU
1 stop13h 05m
Frontier
Wed 9/96:42 pm
SJU
- MKE
1 stop15h 26m
Frontier
Deal found 7/30![Frontier logo]()
$341
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:42 pm
MKE
- SJU
1 stop7h 12m
American Airlines
Sat 8/2912:55 am
SJU
- MKE
1 stop7h 54m
American Airlines
Deal found 7/30![American Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:00 am
MKE
- SJU
1 stop17h 15m
American Airlines
Sun 8/231:38 pm
SJU
- MKE
2 stops10h 36m
American Airlines
Deal found 7/29![American Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 8/2012:10 pm
MKE
- SJU
1 stop13h 05m
Frontier
Mon 8/243:10 am
SJU
- MKE
1 stop9h 03m
Frontier
Deal found 7/29![Frontier logo]()
$352
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:27 pm
MKE
- SJU
2 stops16h 04m
American Airlines
Fri 10/303:51 pm
SJU
- MKE
1 stop9h 06m
American Airlines
Deal found 7/30![American Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:35 am
MKE
- SJU
2 stops9h 22m
American Airlines
Mon 8/3110:33 am
SJU
- MKE
2 stops13h 26m
American Airlines
Deal found 7/31![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:03 pm
MKE
- SJU
1 stop6h 57m
United Airlines
Fri 11/132:05 am
SJU
- MKE
2 stops13h 43m
United Airlines
Deal found 7/27![United Airlines logo]()
$356
This Southwest deal was found by Cheapflights users on 7/30. 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 8/2112:30 pm
MKE
- SJU
2 stops9h 35m
Southwest
Sun 8/239:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 7/30![Southwest logo]()
$361
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:18 am
MKE
- SJU
2 stops12h 20m
United Airlines
Sat 9/121:00 am
SJU
- MKE
2 stops11h 30m
United Airlines
Deal found 7/31![United Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Tue 9/18:30 am
MKE
- SJU
2 stops11h 08m
United Airlines
Sat 9/51:00 am
SJU
- MKE
2 stops12h 38m
United Airlines
Deal found 7/29![United Airlines logo]()
$365
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:55 pm
MKE
- SJU
1 stop13h 25m
Southwest
Fri 11/134:00 pm
SJU
- MKE
2 stops9h 55m
Southwest
Deal found 7/27![Southwest logo]()
$366
Best flights from Milwaukee to Puerto RicoDiscover carefully curated flight deals from Milwaukee to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 1, 2026.
Discover carefully curated flight deals from Milwaukee to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 1, 2026.
This Southwest deal was found by Cheapflights users on 7/31. 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 8/2111:00 am
MKE
- SJU
1 stop11h 05m
Southwest
Sun 8/239:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 7/31![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 7/30. 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 11/710:48 am
MKE
- SJU
2 stops9h 34m
United Airlines
Fri 11/132:05 am
SJU
- MKE
2 stops11h 23m
United Airlines
Deal found 7/30![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:30 am
MKE
- SJU
1 stop7h 15m
Delta
Fri 10/305:59 pm
SJU
- MKE
1 stop6h 54m
Delta
Deal found 7/28![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:15 am
MKE
- SJU
1 stop9h 00m
Southwest
Sat 11/146:45 am
SJU
- MKE
1 stop7h 20m
Southwest
Deal found 7/27![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Tue 11/1010:48 am
MKE
- SJU
1 stop8h 12m
United Airlines
Mon 11/162:05 am
SJU
- MKE
1 stop10h 18m
United Airlines
Deal found 7/29![United Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 7/30. 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 8/299:05 am
MKE
- SJU
1 stop6h 35m
Southwest
Fri 9/46:30 am
SJU
- MKE
2 stops9h 55m
Southwest
Deal found 7/30![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:00 am
MKE
- SJU
2 stops11h 05m
Southwest
Mon 9/216:30 am
SJU
- MKE
2 stops9h 55m
Southwest
Deal found 7/29![Southwest logo]()
$376
This United Airlines deal was found by Cheapflights users on 7/30. 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 11/265:00 am
MKE
- CPX
2 stops10h 21m
United Airlines
Tue 12/110:48 am
CPX
- MKE
2 stops14h 39m
United Airlines
Deal found 7/30![United Airlines logo]()
$1,896
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Tue 11/245:00 am
MKE
- CPX
2 stops10h 21m
United Airlines
Tue 12/110:48 am
CPX
- MKE
2 stops14h 39m
United Airlines
Deal found 7/30![United Airlines logo]()
$1,896
This United Airlines deal was found by Cheapflights users on 7/30. 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 11/266:47 am
MKE
- CPX
2 stops8h 34m
United Airlines
Sun 11/2910:48 am
CPX
- MKE
2 stops13h 59m
United Airlines
Deal found 7/30![United Airlines logo]()
$2,671
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:00 am
MKE
- CPX
2 stops10h 21m
United Airlines
Sun 11/2910:48 am
CPX
- MKE
2 stops13h 59m
United Airlines
Deal found 7/30![United Airlines logo]()
$2,746
Last-minute flights from Milwaukee to Puerto RicoDiscover last-minute flight deals from Milwaukee to Puerto Rico. Data last updated August 1, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Puerto Rico. Data last updated August 1, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 7/31. 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
- SJU
1 stop13h 05m
Frontier
Mon 8/243:10 am
SJU
- MKE
1 stop9h 03m
Frontier
Deal found 7/31![Frontier logo]()
$376
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:00 am
MKE
- SJU
1 stop17h 15m
American Airlines
Sun 8/231:38 pm
SJU
- MKE
2 stops10h 36m
American Airlines
Deal found 7/29![American Airlines logo]()
$351
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:40 am
MKE
- SJU
2 stops10h 30m
Southwest
Sun 8/239:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 7/28![Southwest logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:10 pm
MKE
- SJU
1 stop13h 05m
Frontier
Mon 8/248:57 pm
SJU
- MKE
1 stop15h 16m
Frontier
Deal found 7/28![Frontier logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 8/2012:10 pm
MKE
- SJU
1 stop13h 05m
Frontier
Mon 8/243:10 am
SJU
- MKE
1 stop9h 03m
Frontier
Deal found 7/29![Frontier logo]()
$352
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:30 pm
MKE
- SJU
1 stop9h 20m
Southwest
Sun 8/239:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 7/27![Southwest logo]()
$380
This Southwest deal was found by Cheapflights users on 7/30. 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 8/2112:30 pm
MKE
- SJU
2 stops9h 35m
Southwest
Sun 8/239:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 7/30![Southwest logo]()
$361
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:20 am
MKE
- SJU
2 stops9h 37m
American Airlines
Mon 8/3110:33 am
SJU
- MKE
2 stops13h 26m
American Airlines
Deal found 7/30![American Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:00 am
MKE
- SJU
2 stops11h 30m
American Airlines
Fri 9/41:38 pm
SJU
- MKE
2 stops10h 21m
American Airlines
Deal found 7/30![American Airlines logo]()
$373
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:35 am
MKE
- SJU
2 stops9h 22m
American Airlines
Mon 8/3110:33 am
SJU
- MKE
2 stops13h 26m
American Airlines
Deal found 7/31![American Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:00 am
MKE
- SJU
2 stops12h 30m
American Airlines
Fri 9/43:47 pm
SJU
- MKE
1 stop8h 12m
American Airlines
Deal found 7/30![American Airlines logo]()
$371
One-way flights from Milwaukee to Puerto RicoSearch for one-way flight options from Milwaukee to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
Search for one-way flight options from Milwaukee to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 10/258:10 pm
MKE
- SJU
1 stop19h 24m
Frontier
Deal found 8/1![Frontier logo]()
$165
This Trip.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:10 pm
MKE
- SJU
1 stop16h 06m
Frontier
Deal found 7/31![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/2012:10 pm
MKE
- SJU
1 stop13h 05m
Frontier
Deal found 7/31![Frontier logo]()
$170
This United Airlines deal was found by Cheapflights users on 7/29. 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 8/296:15 am
MKE
- SJU
2 stops13h 23m
United Airlines
Deal found 7/29![United Airlines logo]()
$173
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:20 am
MKE
- SJU
2 stops11h 13m
American Airlines
Deal found 7/27![American Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:28 am
MKE
- SJU
2 stops11h 05m
American Airlines
Deal found 7/30![American Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:27 pm
MKE
- SJU
2 stops16h 04m
American Airlines
Deal found 7/31![American Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:53 pm
MKE
- SJU
2 stops16h 07m
American Airlines
Deal found 7/29![American Airlines logo]()
$182
This Frontier deal was found by Cheapflights users on 7/30. 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 12/105:33 pm
MKE
- SJU
1 stop7h 09m
Frontier
Deal found 7/30![Frontier logo]()
$198
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:01 am
MKE
- SJU
2 stops12h 32m
American Airlines
Deal found 7/31![American Airlines logo]()
$203
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:50 pm
MKE
- SJU
2 stops13h 45m
American Airlines
Deal found 7/30![American Airlines logo]()
$213
Find flight deals from Milwaukee to Puerto Rico
Keep the following information in mind while searching for Milwaukee to Puerto Rico flight deals. Data was last updated August 1, 2026.
Round-trip from | $339 (Kiwi.com) |
|---|---|
One-way from | $165 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $418 |
Cheapflights Fare Finder
Customize your flight search to find flights from Milwaukee to Puerto Rico 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 August 1, 2026.
Use the filters below to find and compare flights from Milwaukee to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 8/21
11:00 am-11:05 pm
1 stop11h 05m
San Juan Luis Munoz Marin Intl
Sun 8/23
9:25 pm-8:55 am
1 stop12h 30m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 11/7
10:48 am-10:22 pm
2 stops9h 34m
San Juan Luis Munoz Marin Intl
Fri 11/13
2:05 am-11:28 am
2 stops11h 23m
$346
Quickest round-trip
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 10/5
5:30 am-1:45 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Fri 10/30
5:59 pm-11:53 pm
1 stop6h 54m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 11/7
6:15 am-5:15 pm
1 stop9h 00m
San Juan Luis Munoz Marin Intl
Sat 11/14
6:45 am-12:05 pm
1 stop7h 20m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 11/10
10:48 am-9:00 pm
1 stop8h 12m
San Juan Luis Munoz Marin Intl
Mon 11/16
2:05 am-10:23 am
1 stop10h 18m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 8/29
9:05 am-4:40 pm
1 stop6h 35m
San Juan Luis Munoz Marin Intl
Fri 9/4
6:30 am-3:25 pm
2 stops9h 55m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 9/16
10:00 am-10:05 pm
2 stops11h 05m
San Juan Luis Munoz Marin Intl
Mon 9/21
6:30 am-3:25 pm
2 stops9h 55m
$376
MilwaukeeCulebra
MKE - CPX
MKECPX
Milwaukee-Mitchell
Thu 11/26
5:00 am-5:21 pm
2 stops10h 21m
Culebra
Tue 12/1
10:48 am-11:27 pm
2 stops14h 39m
$1,896
MilwaukeeCulebra
MKE - CPX
MKECPX
Milwaukee-Mitchell
Tue 11/24
5:00 am-5:21 pm
2 stops10h 21m
Culebra
Tue 12/1
10:48 am-11:27 pm
2 stops14h 39m
$1,896
MilwaukeeCulebra
MKE - CPX
MKECPX
Milwaukee-Mitchell
Thu 11/26
6:47 am-5:21 pm
2 stops8h 34m
Culebra
Sun 11/29
10:48 am-10:47 pm
2 stops13h 59m
$2,671
Showing 1-10 of 21 resultsSorted by cheapest first
Best time to book a flight from Milwaukee to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Milwaukee with our price prediction graph.
MKE-SJU
MKE-CPX
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 Puerto Rico
MKE-PR0
MKE-SJU
MKE-CPX
What is the cheapest month to book a flight from Milwaukee to Puerto Rico?
Currently, October is the cheapest month in which you can book a flight from Milwaukee to Puerto Rico (average of $326). Flying from Milwaukee to Puerto Rico in December is currently the most expensive (average of $736). 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.
How far ahead should I book a flight from Milwaukee to Puerto Rico?
To ensure you get the cheapest price possible for a flight from Milwaukee to Puerto Rico, you should look to book at least 52 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.
Reviews of airlines servicing Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated August 1, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Milwaukee to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Puerto Rico. 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 Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Puerto Rico by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Milwaukee to Puerto Rico by cabin class
Find flights from Milwaukee to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Milwaukee and Puerto Rico flights
Browse other Milwaukee and Puerto Rico flight options. Last updated on August 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Milwaukee to Puerto Rico
Discover the top 5 airlines that operate flights from Milwaukee to Puerto Rico. 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 August 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$358 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$143 | Average$398 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$510 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$497 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$317 | Average$483 | FlexibilityNo cancel fee | On-time63% |