Find a great deal and save up to 66% by booking at least 54 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Wisconsin to Caribbean within the next two weeks, with the cheapest ticket starting at $308.
Due to multiple factors, expect to potentially pay more when booking in December. For low rates, September can be a great choice for travel to Caribbean. Flights to Caribbean from Wisconsin in September are about $435 on average during September, but can be found for as low as $178.
When flying from Wisconsin to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$217 - $440
Route
Depart
Return
Price
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 5/16
1 stop15h 49m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop13h 30m
Milwaukee-MitchellSaint Thomas Island Cyril E King
MKE - STT
MKESTT
Milwaukee-Mitchell
Tue 5/28
1 stop28h 32m
Saint Thomas Island Cyril E King
Wed 6/5
1 stop9h 22m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 5/16
1 stop15h 49m
San Juan Luis Munoz Marin Intl
Mon 5/20
1 stop7h 27m
Milwaukee-MitchellSaint Thomas Island Cyril E King
MKE - STT
MKESTT
Milwaukee-Mitchell
Tue 5/28
2 stops27h 19m
Saint Thomas Island Cyril E King
Wed 6/5
1 stop9h 22m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 5/18
1 stop18h 41m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop13h 30m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 9/7
2 stops16h 59m
San Juan Luis Munoz Marin Intl
Sat 9/14
1 stop8h 28m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 5/15
1 stop7h 44m
San Juan Luis Munoz Marin Intl
Thu 5/23
1 stop8h 57m
Madison Truax FieldSan Juan Luis Munoz Marin Intl
MSN - SJU
MSNSJU
Madison Truax Field
Sat 9/28
1 stop7h 00m
San Juan Luis Munoz Marin Intl
Tue 10/1
1 stop8h 00m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 5/14
1 stop8h 35m
San Juan Luis Munoz Marin Intl
Tue 5/14
1 stop8h 16m
No data available for this route at this time. Please check back soon.
Comfort
Entertainment
Overall
Crew
Food
Boarding
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Comfort
Entertainment
Overall
Crew
Food
Boarding
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Comfort
Entertainment
Overall
Crew
Food
Boarding
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Comfort
Entertainment
Overall
Crew
Food
Boarding
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Comfort
Entertainment
Overall
Crew
Food
Boarding
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Comfort
Entertainment
Overall
Crew
Food
Boarding
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
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