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
$115 - $373
Route
Depart
Return
Price
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/27
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Wed 8/28
Nonstop5h 13m
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 8/27
1 stop13h 11m
San Juan Luis Munoz Marin Intl
Tue 8/27
2 stops17h 27m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 8/26
1 stop16h 53m
San Juan Luis Munoz Marin Intl
Wed 8/28
Nonstop5h 13m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/20
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Tue 8/27
1 stop20h 57m
Chicago O'Hare IntlPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Tue 7/2
1 stop9h 02m
Punta Cana
Fri 7/12
1 stop9h 03m
Chicago O'Hare IntlPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 7/8
Nonstop4h 46m
Punta Cana
Thu 7/11
1 stop10h 43m
Chicago O'Hare IntlPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sat 8/24
1 stop17h 05m
Punta Cana
Thu 8/29
Nonstop5h 00m
Chicago O'Hare IntlNassau Intl
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Wed 8/14
1 stop6h 14m
Nassau Intl
Tue 8/20
1 stop7h 18m
No data available for this route at this time. Please check back soon.
Comfort
Crew
Overall
Boarding
Food
Entertainment
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Comfort
Crew
Overall
Boarding
Food
Entertainment
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Comfort
Crew
Overall
Boarding
Food
Entertainment
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Comfort
Crew
Overall
Boarding
Food
Entertainment
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Comfort
Crew
Overall
Boarding
Food
Entertainment
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Comfort
Crew
Overall
Boarding
Food
Entertainment
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
20%of flight departures | Early morningMidnight to 6 am |
---|---|
80%of flight departures | Morning6 am to noon |
0%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
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