Travelers have found it’s best to book a flight 57 days in advance to save up to 17% 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 $270, or $335 for flights within the next 24 hours.
September is one of the best times of the year to fly to Caribbean from Chicago. Prices for September average $370 per person but you can even find prices for as low as $111. The most expensive prices can be found in the month of March. Opting for a September flight can save you 50% 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
$174 - $266
Route
Depart
Return
Price
Chicago O'Hare IntlSaint Thomas Island Cyril E King
ORD - STT
ORDSTT
Chicago O'Hare Intl
Wed 6/5
1 stop14h 55m
Saint Thomas Island Cyril E King
Wed 6/12
1 stop8h 10m
Chicago O'Hare IntlSaint Thomas Island Cyril E King
ORD - STT
ORDSTT
Chicago O'Hare Intl
Wed 6/5
1 stop14h 00m
Saint Thomas Island Cyril E King
Tue 6/11
1 stop17h 27m
Chicago O'Hare IntlSaint Thomas Island Cyril E King
ORD - STT
ORDSTT
Chicago O'Hare Intl
Wed 5/29
1 stop13h 54m
Saint Thomas Island Cyril E King
Wed 6/5
1 stop9h 10m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/14
1 stop7h 05m
San Juan Luis Munoz Marin Intl
Wed 5/15
Nonstop5h 10m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/14
1 stop20h 42m
San Juan Luis Munoz Marin Intl
Mon 5/20
1 stop10h 54m
Chicago MidwayPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Wed 5/29
1 stop20h 33m
Punta Cana
Tue 6/4
1 stop21h 34m
Chicago MidwayPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Wed 5/29
1 stop20h 33m
Punta Cana
Sun 6/2
1 stop25h 11m
Chicago O'Hare IntlPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 5/13
Nonstop4h 35m
Punta Cana
Wed 5/15
Nonstop5h 05m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 5/6
Nonstop4h 50m
San Juan Luis Munoz Marin Intl
Mon 5/6
1 stop9h 30m
No data available for this route at this time. Please check back soon.
Comfort
Boarding
Entertainment
Food
Overall
Crew
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Boarding
Entertainment
Food
Overall
Crew
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Boarding
Entertainment
Food
Overall
Crew
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Boarding
Entertainment
Food
Overall
Crew
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Boarding
Entertainment
Food
Overall
Crew
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Comfort
Boarding
Entertainment
Food
Overall
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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