To save up to 20% 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 $280 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 $318 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
$120 - $237
Route
Depart
Return
Price
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/21
1 stop13h 11m
San Juan Luis Munoz Marin Intl
Sat 5/25
1 stop9h 00m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 6/4
1 stop17h 00m
San Juan Luis Munoz Marin Intl
Sat 6/8
1 stop8h 21m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 5/29
Nonstop4h 53m
San Juan Luis Munoz Marin Intl
Tue 6/4
1 stop20h 49m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 5/29
Nonstop4h 53m
San Juan Luis Munoz Marin Intl
Tue 6/4
1 stop13h 54m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/18
1 stop13h 27m
San Juan Luis Munoz Marin Intl
Sat 5/25
1 stop8h 01m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/21
1 stop11h 28m
San Juan Luis Munoz Marin Intl
Sat 5/25
1 stop9h 00m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/18
1 stop7h 13m
San Juan Luis Munoz Marin Intl
Fri 5/31
1 stop13h 55m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 5/18
1 stop20h 11m
Simpson Bay Princess Juliana
Sat 5/25
1 stop9h 44m
Chicago O'Hare IntlPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 5/12
Nonstop4h 35m
Punta Cana
Thu 5/16
Nonstop5h 05m
No data available for this route at this time. Please check back soon.
Comfort
Boarding
Crew
Food
Overall
Entertainment
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Boarding
Crew
Food
Overall
Entertainment
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Boarding
Crew
Food
Overall
Entertainment
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Boarding
Crew
Food
Overall
Entertainment
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Boarding
Crew
Food
Overall
Entertainment
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Boarding
Crew
Food
Overall
Entertainment
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
9%of flight departures | Early morningMidnight to 6 am |
---|---|
91%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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