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
$114 - $375
Route
Depart
Return
Price
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/21
1 stop20h 42m
San Juan Luis Munoz Marin Intl
Tue 5/28
1 stop13h 48m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 9/11
1 stop13h 11m
San Juan Luis Munoz Marin Intl
Tue 9/17
1 stop10h 28m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 6/4
Nonstop4h 53m
San Juan Luis Munoz Marin Intl
Tue 6/11
1 stop9h 29m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 9/4
1 stop7h 38m
San Juan Luis Munoz Marin Intl
Wed 9/11
1 stop7h 29m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/28
1 stop20h 42m
San Juan Luis Munoz Marin Intl
Sat 6/1
1 stop9h 00m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 5/29
1 stop28h 06m
San Juan Luis Munoz Marin Intl
Tue 6/4
1 stop23h 42m
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
Tue 5/28
1 stop14h 58m
Chicago O'Hare IntlPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Tue 7/2
Nonstop4h 39m
Punta Cana
Fri 7/12
1 stop9h 08m
Chicago O'Hare IntlPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Wed 7/10
1 stop15h 43m
Punta Cana
Sun 7/14
Nonstop5h 00m
No data available for this route at this time. Please check back soon.
Boarding
Entertainment
Food
Overall
Comfort
Crew
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Entertainment
Food
Overall
Comfort
Crew
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Entertainment
Food
Overall
Comfort
Crew
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Entertainment
Food
Overall
Comfort
Crew
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Entertainment
Food
Overall
Comfort
Crew
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Entertainment
Food
Overall
Comfort
Crew
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
8%of flight departures | Early morningMidnight to 6 am |
---|---|
92%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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