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
$223 - $420
Route
Depart
Return
Price
Milwaukee-MitchellSaint Thomas Island Cyril E King
MKE - STT
MKESTT
Milwaukee-Mitchell
Sat 5/11
2 stops20h 37m
Saint Thomas Island Cyril E King
Mon 5/13
2 stops21h 04m
Milwaukee-MitchellSaint Thomas Island Cyril E King
MKE - STT
MKESTT
Milwaukee-Mitchell
Sun 5/12
2 stops10h 03m
Saint Thomas Island Cyril E King
Tue 5/14
2 stops21h 04m
Milwaukee-MitchellSaint Thomas Island Cyril E King
MKE - STT
MKESTT
Milwaukee-Mitchell
Sat 5/18
1 stop8h 33m
Saint Thomas Island Cyril E King
Sat 5/25
1 stop9h 11m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 5/16
1 stop15h 49m
San Juan Luis Munoz Marin Intl
Sat 5/25
1 stop7h 27m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 5/18
2 stops29h 17m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop28h 57m
Milwaukee-MitchellSaint Thomas Island Cyril E King
MKE - STT
MKESTT
Milwaukee-Mitchell
Sat 5/18
1 stop8h 33m
Saint Thomas Island Cyril E King
Thu 5/23
1 stop9h 11m
Milwaukee-MitchellSaint Thomas Island Cyril E King
MKE - STT
MKESTT
Milwaukee-Mitchell
Sat 5/11
1 stop8h 07m
Saint Thomas Island Cyril E King
Wed 5/15
1 stop10h 09m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 5/8
1 stop8h 35m
San Juan Luis Munoz Marin Intl
Tue 5/14
1 stop8h 16m
Milwaukee-MitchellNassau Intl
MKE - NAS
MKENAS
Milwaukee-Mitchell
Tue 4/30
1 stop5h 18m
Nassau Intl
Thu 5/2
2 stops18h 22m
No data available for this route at this time. Please check back soon.
Boarding
Entertainment
Overall
Comfort
Crew
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Boarding
Entertainment
Overall
Comfort
Crew
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Boarding
Entertainment
Overall
Comfort
Crew
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Boarding
Entertainment
Overall
Comfort
Crew
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Boarding
Entertainment
Overall
Comfort
Crew
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Boarding
Entertainment
Overall
Comfort
Crew
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
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