Travelers have found it’s best to book a flight 21 days in advance to save up to 30% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 21 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Cleveland to Caribbean 1-2 weeks in advance for as low as $228, or $387 for flights within the next 24 hours.
The best pricing can be found in the month of September. Prices to Caribbean from Cleveland average $303. You can even find prices in September for less than $303, as users have found deals to Caribbean from as low as $129. The month of December appears to be one of the more expensive times to travel to Caribbean from Cleveland. Flying in the targeted month can save you up to 53%.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Cleveland to Caribbean as you normally would.
Fly from
Fly to
Budget
$153 - $315
Route
Depart
Return
Price
Cleveland Hopkins IntlSan Juan Luis Munoz Marin Intl
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Wed 10/23
1 stop10h 24m
San Juan Luis Munoz Marin Intl
Tue 10/29
1 stop28h 40m
Cleveland Hopkins IntlSan Juan Luis Munoz Marin Intl
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Tue 10/22
1 stop10h 24m
San Juan Luis Munoz Marin Intl
Tue 10/29
1 stop28h 40m
Cleveland Hopkins IntlSan Juan Luis Munoz Marin Intl
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Mon 8/19
1 stop10h 39m
San Juan Luis Munoz Marin Intl
Fri 8/23
1 stop27h 10m
Cleveland Hopkins IntlSan Juan Luis Munoz Marin Intl
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Mon 8/19
1 stop10h 39m
San Juan Luis Munoz Marin Intl
Wed 8/21
1 stop27h 10m
Cleveland Hopkins IntlSan Juan Luis Munoz Marin Intl
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Wed 7/24
Nonstop4h 20m
San Juan Luis Munoz Marin Intl
Wed 8/7
Nonstop4h 30m
Cleveland Hopkins IntlSan Juan Luis Munoz Marin Intl
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Wed 7/31
1 stop11h 43m
San Juan Luis Munoz Marin Intl
Wed 8/7
Nonstop4h 30m
Cleveland Hopkins IntlSan Juan Luis Munoz Marin Intl
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sat 7/27
Nonstop4h 20m
San Juan Luis Munoz Marin Intl
Tue 8/6
Nonstop4h 30m
Cleveland Hopkins IntlSaint Thomas Island Cyril E King
CLE - STT
CLESTT
Cleveland Hopkins Intl
Sun 8/18
1 stop6h 44m
Saint Thomas Island Cyril E King
Mon 8/26
1 stop6h 34m
Cleveland Hopkins IntlSanto Domingo Las Americas
CLE - SDQ
CLESDQ
Cleveland Hopkins Intl
Mon 9/9
2 stops15h 33m
Santo Domingo Las Americas
Fri 9/20
2 stops17h 01m
No data available for this route at this time. Please check back soon.
Comfort
Food
Overall
Crew
Boarding
Entertainment
Reviews
Great airline! I would fly with them again. Overall, very positive experience along every step of the way. I was so jazzed they offer direct flights from Denver to Anchorage! Great customer service.
Comfort
Food
Overall
Crew
Boarding
Entertainment
Reviews
Great airline! I would fly with them again. Overall, very positive experience along every step of the way. I was so jazzed they offer direct flights from Denver to Anchorage! Great customer service.
Comfort
Food
Overall
Crew
Boarding
Entertainment
Reviews
Great airline! I would fly with them again. Overall, very positive experience along every step of the way. I was so jazzed they offer direct flights from Denver to Anchorage! Great customer service.
Comfort
Food
Overall
Crew
Boarding
Entertainment
Reviews
Great airline! I would fly with them again. Overall, very positive experience along every step of the way. I was so jazzed they offer direct flights from Denver to Anchorage! Great customer service.
Comfort
Food
Overall
Crew
Boarding
Entertainment
Reviews
Great airline! I would fly with them again. Overall, very positive experience along every step of the way. I was so jazzed they offer direct flights from Denver to Anchorage! Great customer service.
Comfort
Food
Overall
Crew
Boarding
Entertainment
Reviews
Great airline! I would fly with them again. Overall, very positive experience along every step of the way. I was so jazzed they offer direct flights from Denver to Anchorage! Great customer service.
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Cheapest$119 | Average$316 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$138 | Average$396 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$184 | Average$627 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$238 | Average$555 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$248 | Average$605 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$268 | Average$595 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$416 | Average$970 | FlexibilityNo cancel fee | On-time67% | |
Cheapest$451 | Average$545 | FlexibilityNo cancel fee | On-time75% | |
Cheapest$59,048 | Average$78,728 | FlexibilityNo cancel fee | On-timeN/A |
0%of flight departures | Early morningMidnight to 6 am |
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100%of flight departures | Morning6 am to noon |
0%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |