To save up to 66% on this flight, we recommend booking at least 54 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 $308 1-2 weeks out and tickets from $640 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
$158 - $418
Route
Depart
Return
Price
Milwaukee-MitchellSaint Thomas Island Cyril E King
MKE - STT
MKESTT
Milwaukee-Mitchell
Tue 4/9
1 stop6h 30m
Saint Thomas Island Cyril E King
Thu 4/18
1 stop9h 48m
Milwaukee-MitchellSaint Thomas Island Cyril E King
MKE - STT
MKESTT
Milwaukee-Mitchell
Tue 4/9
1 stop8h 41m
Saint Thomas Island Cyril E King
Tue 4/16
1 stop11h 23m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 5/7
1 stop19h 41m
San Juan Luis Munoz Marin Intl
Tue 5/14
1 stop29h 08m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 4/23
1 stop19h 33m
San Juan Luis Munoz Marin Intl
Tue 4/30
1 stop29h 32m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 4/6
1 stop14h 27m
San Juan Luis Munoz Marin Intl
Sat 4/13
1 stop15h 35m
Milwaukee-MitchellChristiansted Henry Rohlsen
MKE - STX
MKESTX
Milwaukee-Mitchell
Sat 6/1
2 stops21h 25m
Christiansted Henry Rohlsen
Fri 6/7
2 stops19h 09m
Milwaukee-MitchellNassau Intl
MKE - NAS
MKENAS
Milwaukee-Mitchell
Wed 4/10
1 stop4h 56m
Nassau Intl
Tue 4/16
1 stop8h 31m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 5/3
1 stop8h 20m
San Juan Luis Munoz Marin Intl
Fri 5/10
1 stop8h 16m
Milwaukee-MitchellNassau Intl
MKE - NAS
MKENAS
Milwaukee-Mitchell
Tue 4/30
1 stop8h 48m
Nassau Intl
Thu 5/2
2 stops18h 22m
No data available for this route at this time. Please check back soon.
Boarding
Food
Entertainment
Comfort
Overall
Crew
Reviews
It was a good experience other than a short delay.
Boarding
Food
Entertainment
Comfort
Overall
Crew
Reviews
It was a good experience other than a short delay.
Boarding
Food
Entertainment
Comfort
Overall
Crew
Reviews
It was a good experience other than a short delay.
Boarding
Food
Entertainment
Comfort
Overall
Crew
Reviews
It was a good experience other than a short delay.
Boarding
Food
Entertainment
Comfort
Overall
Crew
Reviews
It was a good experience other than a short delay.
Boarding
Food
Entertainment
Comfort
Overall
Crew
Reviews
It was a good experience other than a short delay.
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