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 $330 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
$284 - $420
Route
Depart
Return
Price
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 5/21
2 stops10h 54m
San Juan Luis Munoz Marin Intl
Wed 5/29
3 stops33h 37m
Milwaukee-MitchellPunta Cana
MKE - PUJ
MKEPUJ
Milwaukee-Mitchell
Tue 8/6
1 stop22h 40m
Punta Cana
Mon 8/12
1 stop21h 10m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 5/28
1 stop12h 26m
San Juan Luis Munoz Marin Intl
Tue 6/4
2 stops11h 19m
Milwaukee-MitchellSaint Thomas Island Cyril E King
MKE - STT
MKESTT
Milwaukee-Mitchell
Tue 8/20
1 stop6h 58m
Saint Thomas Island Cyril E King
Wed 8/28
1 stop14h 05m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 7/16
1 stop12h 06m
San Juan Luis Munoz Marin Intl
Mon 7/22
1 stop7h 47m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 7/27
1 stop9h 57m
San Juan Luis Munoz Marin Intl
Wed 8/21
1 stop11h 11m
Milwaukee-MitchellSan Juan Luis Munoz Marin Intl
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sun 7/14
2 stops15h 33m
San Juan Luis Munoz Marin Intl
Sat 8/31
2 stops20h 16m
Milwaukee-MitchellNassau Intl
MKE - NAS
MKENAS
Milwaukee-Mitchell
Wed 7/17
1 stop6h 54m
Nassau Intl
Wed 7/24
1 stop10h 47m
Milwaukee-MitchellNassau Intl
MKE - NAS
MKENAS
Milwaukee-Mitchell
Tue 5/28
2 stops19h 29m
Nassau Intl
Fri 5/31
1 stop9h 29m
No data available for this route at this time. Please check back soon.
Food
Crew
Entertainment
Overall
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.
Food
Crew
Entertainment
Overall
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.
Food
Crew
Entertainment
Overall
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.
Food
Crew
Entertainment
Overall
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.
Food
Crew
Entertainment
Overall
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.
Food
Crew
Entertainment
Overall
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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