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 Milwaukee to Caribbean from $332 1-2 weeks out and tickets from $396 for flights departing within the next 72 hours.
Flights from Milwaukee to Caribbean lean towards being more expensive in December. Prices are generally better when you fly from Milwaukee to Caribbean in September, with the cheapest ticket starting at $178.
When flying from Milwaukee 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
$282 - $494
Route
Depart
Return
Price
Milwaukee-MitchellChristiansted Henry Rohlsen
MKE - STX
MKESTX
Milwaukee-Mitchell
Mon 9/9
2 stops19h 24m
Christiansted Henry Rohlsen
Wed 9/11
2 stops20h 19m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 8/13
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Sat 8/24
2 stops10h 06m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 8/21
1 stop11h 30m
San Juan Luis Munoz Marin Intl
Tue 9/3
1 stop23h 51m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 8/13
1 stop12h 06m
San Juan Luis Munoz Marin Intl
Sat 8/24
1 stop10h 52m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 6/12
2 stops28h 27m
San Juan Luis Munoz Marin Intl
Sat 6/15
1 stop24h 18m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 6/14
1 stop16h 15m
San Juan Luis Munoz Marin Intl
Sat 6/22
1 stop6h 56m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 8/9
1 stop10h 15m
San Juan Luis Munoz Marin Intl
Sat 8/17
1 stop6h 44m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 6/13
1 stop9h 07m
San Juan Luis Munoz Marin Intl
Tue 6/18
1 stop10h 54m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 8/13
2 stops13h 38m
San Juan Luis Munoz Marin Intl
Fri 8/23
2 stops11h 31m
No data available for this route at this time. Please check back soon.
Entertainment
Comfort
Boarding
Overall
Crew
Food
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.
Entertainment
Comfort
Boarding
Overall
Crew
Food
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.
Entertainment
Comfort
Boarding
Overall
Crew
Food
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.
Entertainment
Comfort
Boarding
Overall
Crew
Food
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.
Entertainment
Comfort
Boarding
Overall
Crew
Food
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.
Entertainment
Comfort
Boarding
Overall
Crew
Food
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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