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
$129 - $351
Route
Depart
Return
Price
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/20
1 stop7h 38m
San Juan Luis Munoz Marin Intl
Tue 8/27
1 stop14h 31m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 9/10
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Tue 9/24
1 stop14h 36m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/20
1 stop7h 36m
San Juan Luis Munoz Marin Intl
Tue 8/27
Nonstop4h 59m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/20
1 stop17h 37m
San Juan Luis Munoz Marin Intl
Tue 8/27
1 stop15h 01m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/20
1 stop17h 37m
San Juan Luis Munoz Marin Intl
Mon 8/26
2 stops31h 05m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 6/11
1 stop10h 19m
San Juan Luis Munoz Marin Intl
Tue 6/18
2 stops25h 41m
Chicago O'Hare IntlPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Fri 7/26
1 stop13h 54m
Punta Cana
Thu 8/1
Nonstop5h 03m
Chicago O'Hare IntlNassau Intl
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Wed 6/12
1 stop5h 22m
Nassau Intl
Tue 6/18
1 stop12h 04m
Chicago O'Hare IntlNassau Intl
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Wed 6/12
1 stop7h 40m
Nassau Intl
Tue 6/18
1 stop16h 45m
No data available for this route at this time. Please check back soon.
Overall
Boarding
Food
Crew
Entertainment
Comfort
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.
Overall
Boarding
Food
Crew
Entertainment
Comfort
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.
Overall
Boarding
Food
Crew
Entertainment
Comfort
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.
Overall
Boarding
Food
Crew
Entertainment
Comfort
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.
Overall
Boarding
Food
Crew
Entertainment
Comfort
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.
Overall
Boarding
Food
Crew
Entertainment
Comfort
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.
3%of flight departures | Early morningMidnight to 6 am |
---|---|
94%of flight departures | Morning6 am to noon |
3%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
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