To save up to 25% on this flight, we recommend booking at least 57 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago O'Hare Intl Airport to Caribbean from $258 1-2 weeks out and tickets from $283 for flights departing within the next 72 hours.
Our data shows that October tends to be the cheapest month to fly to Caribbean from Chicago O'Hare Intl Airport. Users have commonly found prices around $319 for the month, but tickets can be as low as $90. Due to multiple factors, prepare for potentially higher prices in March.
When flying from Chicago O'Hare Intl Airport 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
$184 - $402
Route
Depart
Return
Price
Chicago O'Hare IntlSaint Thomas Island Cyril E King
ORD - STT
ORDSTT
Chicago O'Hare Intl
Tue 9/10
1 stop15h 09m
Saint Thomas Island Cyril E King
Tue 9/17
1 stop11h 05m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 7/8
1 stop6h 23m
San Juan Luis Munoz Marin Intl
Wed 7/17
Nonstop5h 09m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 7/16
Nonstop4h 47m
San Juan Luis Munoz Marin Intl
Tue 7/23
1 stop10h 14m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 6/23
1 stop9h 19m
San Juan Luis Munoz Marin Intl
Tue 7/16
1 stop10h 14m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 7/9
1 stop9h 10m
San Juan Luis Munoz Marin Intl
Mon 7/15
1 stop22h 21m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 7/23
1 stop7h 19m
San Juan Luis Munoz Marin Intl
Tue 7/30
1 stop10h 38m
Chicago O'Hare IntlPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Fri 8/16
1 stop7h 24m
Punta Cana
Fri 8/23
1 stop16h 54m
Chicago O'Hare IntlNassau Intl
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Wed 7/17
1 stop7h 43m
Nassau Intl
Tue 7/30
1 stop7h 48m
Chicago O'Hare IntlNassau Intl
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Wed 7/31
1 stop6h 50m
Nassau Intl
Sun 8/4
Nonstop3h 45m
No data available for this route at this time. Please check back soon.
Entertainment
Comfort
Boarding
Food
Overall
Crew
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.
Entertainment
Comfort
Boarding
Food
Overall
Crew
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.
Entertainment
Comfort
Boarding
Food
Overall
Crew
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.
Entertainment
Comfort
Boarding
Food
Overall
Crew
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.
Entertainment
Comfort
Boarding
Food
Overall
Crew
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.
Entertainment
Comfort
Boarding
Food
Overall
Crew
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.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Frontier | Cheapest$90 | Average$316 | FlexibilityNo cancel fee | On-time62% |
Spirit Airlines | Cheapest$130 | Average$399 | FlexibilityNo cancel fee | On-time65% |
Delta | Cheapest$134 | Average$526 | FlexibilityNo cancel fee | On-timeN/A |
United Airlines | Cheapest$153 | Average$609 | FlexibilityNo cancel fee | On-time69% |
JetBlue | Cheapest$172 | Average$543 | FlexibilityNo cancel fee | On-time62% |
Aeromexico | Cheapest$262 | Average$548 | FlexibilityNo cancel fee | On-timeN/A |
Air Canada | Cheapest$283 | Average$846 | FlexibilityNo cancel fee | On-time67% |
Alaska Airlines | Cheapest$288 | Average$659 | FlexibilityNo cancel fee | On-time75% |
American Airlines | Cheapest$292 | Average$606 | FlexibilityNo cancel fee | On-time71% |
Lufthansa | Cheapest$403 | Average$445 | FlexibilityNo cancel fee | On-time76% |
11%of flight departures | Early morningMidnight to 6 am |
---|---|
89%of flight departures | Morning6 am to noon |
0%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |