To save up to 90% on this flight, we recommend booking at least 50 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Wisconsin to Caribbean Islands from $332 1-2 weeks out and tickets from $396 for flights departing within the next 72 hours.
Our data shows that September tends to be the cheapest month to fly to Caribbean Islands from Wisconsin. Users have commonly found prices around $440 for the month, but tickets can be as low as $178. Due to multiple factors, prepare for potentially higher prices in December.
When flying from Wisconsin to Caribbean Islands, 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
$113 - $336
Route
Depart
Return
Price
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
Tue 8/20
1 stop7h 36m
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
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
Tue 9/10
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Tue 9/24
1 stop29h 03m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/27
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Tue 8/27
2 stops17h 27m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/27
1 stop13h 11m
San Juan Luis Munoz Marin Intl
Sat 8/31
1 stop11h 50m
Chicago O'Hare IntlPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 7/7
Nonstop4h 44m
Punta Cana
Thu 7/11
Nonstop5h 03m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 8/21
2 stops9h 40m
San Juan Luis Munoz Marin Intl
Wed 9/4
2 stops18h 03m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 11/5
1 stop8h 19m
San Juan Luis Munoz Marin Intl
Tue 11/19
1 stop10h 17m
No data available for this route at this time. Please check back soon.
Crew
Overall
Entertainment
Food
Comfort
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.
Crew
Overall
Entertainment
Food
Comfort
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.
Crew
Overall
Entertainment
Food
Comfort
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.
Crew
Overall
Entertainment
Food
Comfort
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.
Crew
Overall
Entertainment
Food
Comfort
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.
Crew
Overall
Entertainment
Food
Comfort
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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