Find a great deal and save up to 90% by booking at least 50 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 $330.
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 $438 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
$114 - $338
Route
Depart
Return
Price
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 5/29
Nonstop4h 53m
San Juan Luis Munoz Marin Intl
Tue 6/4
1 stop13h 54m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 5/29
Nonstop4h 53m
San Juan Luis Munoz Marin Intl
Tue 6/4
Nonstop5h 10m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/20
1 stop13h 11m
San Juan Luis Munoz Marin Intl
Tue 8/27
1 stop10h 28m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 5/29
Nonstop4h 53m
San Juan Luis Munoz Marin Intl
Tue 6/4
1 stop13h 54m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/20
1 stop7h 38m
San Juan Luis Munoz Marin Intl
Tue 8/27
1 stop10h 28m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 5/30
1 stop10h 46m
San Juan Luis Munoz Marin Intl
Tue 6/4
1 stop13h 54m
Minneapolis St PaulSan Juan Luis Munoz Marin Intl
MSP - SJU
MSPSJU
Minneapolis St Paul
Tue 6/4
1 stop7h 48m
San Juan Luis Munoz Marin Intl
Wed 6/12
1 stop9h 01m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 9/21
1 stop15h 07m
San Juan Luis Munoz Marin Intl
Fri 9/27
2 stops12h 55m
Minneapolis St PaulSan Juan Luis Munoz Marin Intl
MSP - SJU
MSPSJU
Minneapolis St Paul
Sat 6/29
Nonstop5h 14m
San Juan Luis Munoz Marin Intl
Sat 7/13
Nonstop5h 43m
No data available for this route at this time. Please check back soon.
Boarding
Comfort
Food
Crew
Overall
Entertainment
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.
Boarding
Comfort
Food
Crew
Overall
Entertainment
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.
Boarding
Comfort
Food
Crew
Overall
Entertainment
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.
Boarding
Comfort
Food
Crew
Overall
Entertainment
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.
Boarding
Comfort
Food
Crew
Overall
Entertainment
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.
Boarding
Comfort
Food
Crew
Overall
Entertainment
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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