Travelers have found it’s best to book a flight 57 days in advance to save up to 25% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 57 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Caribbean 1-2 weeks in advance for as low as $258, or $283 for flights within the next 24 hours.
October is one of the best times of the year to fly to Caribbean from Chicago. Prices for October average $319 per person but you can even find prices for as low as $90. The most expensive prices can be found in the month of March. Opting for a October flight can save you 60% on your journey compared to booking in March
When flying from Chicago 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
$140 - $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 stop17h 37m
San Juan Luis Munoz Marin Intl
Tue 8/27
1 stop20h 03m
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 8/20
1 stop17h 37m
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
Nonstop4h 59m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 8/28
Nonstop4h 47m
San Juan Luis Munoz Marin Intl
Mon 9/2
1 stop11h 21m
Chicago MidwayPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 7/8
1 stop15h 14m
Punta Cana
Thu 7/18
1 stop23h 46m
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 IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 11/1
1 stop8h 55m
San Juan Luis Munoz Marin Intl
Tue 11/5
1 stop11h 26m
Chicago O'Hare IntlNassau Intl
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Wed 6/12
1 stop7h 40m
Nassau Intl
Tue 6/18
1 stop7h 51m
No data available for this route at this time. Please check back soon.
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
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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