Round-trip from | $216 (eDestinos) |
---|---|
One-way from | $102 (Cheapflightsfares) |
Popular in | December |
Cheapest in | August |
Average price | $351 |
Good round-trip deal | $328 or less |
Good one-way deal | $166 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 5/11
11:30 am-5:16 pm
Nonstop4h 46m
San Juan Luis Munoz Marin Intl
Thu 5/15
6:09 am-10:25 am
Nonstop5h 16m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/10
4:35 pm-10:45 am
1 stop17h 10m
San Juan Luis Munoz Marin Intl
Sat 5/17
9:58 pm-8:43 am
1 stop11h 45m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 5/4
4:15 pm-12:05 am
1 stop6h 50m
San Juan Luis Munoz Marin Intl
Fri 5/9
2:34 pm-11:32 pm
1 stop9h 58m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/2
1:19 pm-10:01 pm
1 stop7h 42m
San Juan Luis Munoz Marin Intl
Sun 5/4
9:58 pm-5:28 pm
1 stop20h 30m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Thu 5/8
6:10 am-11:51 am
Nonstop4h 41m
Punta Cana
Wed 5/14
5:54 pm-10:00 pm
Nonstop5h 06m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sat 5/3
4:15 pm-11:44 am
1 stop18h 29m
Punta Cana
Fri 5/16
5:08 pm-9:11 pm
Nonstop5h 03m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 4/28
5:10 am-12:50 pm
1 stop6h 40m
Punta Cana
Fri 5/2
12:54 pm-8:58 pm
1 stop9h 04m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 5/8
8:45 am-6:05 pm
1 stop8h 20m
San Juan Luis Munoz Marin Intl
Tue 5/13
1:58 pm-9:54 pm
1 stop8h 56m
ChicagoOranjestad
ORD - AUA
ORDAUA
Chicago O'Hare Intl
Sat 5/10
5:05 am-2:40 pm
1 stop8h 35m
Oranjestad Reina Beatrix
Sat 5/17
3:45 pm-12:05 am
1 stop9h 20m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 5/11
9:23 am-3:05 pm
Nonstop4h 42m
Punta Cana
Thu 5/15
1:50 pm-5:55 pm
Nonstop5h 05m
Currently, September is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $254). Flying from Chicago to Caribbean in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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.
The most flights from CHI to 0CB are scheduled on a Monday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 on average).
In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.
If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).
Entertainment
Boarding
Comfort
Food
Crew
Overall
Reviews
Anonymous,Apr 2025
LAS - STS
Entertainment
Boarding
Comfort
Food
Crew
Overall
Reviews
Anonymous,Apr 2025
LAS - STS
Entertainment
Boarding
Comfort
Food
Crew
Overall
Reviews
Anonymous,Apr 2025
LAS - STS
Entertainment
Boarding
Comfort
Food
Crew
Overall
Reviews
Anonymous,Apr 2025
LAS - STS
Entertainment
Boarding
Comfort
Food
Crew
Overall
Reviews
Anonymous,Apr 2025
LAS - STS
Entertainment
Boarding
Comfort
Food
Crew
Overall
Reviews
Anonymous,Apr 2025
LAS - STS
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$124 | Average$348 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$144 | Average$359 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$222 | Average$635 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$226 | Average$641 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$226 | Average$537 | FlexibilityNo cancel fee | On-time70% | |
Cheapest$293 | Average$503 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$331 | Average$648 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$335 | Average$768 | FlexibilityNo cancel fee | On-time67% | |
Cheapest$342 | Average$672 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$397 | Average$953 | FlexibilityNo cancel fee | On-time71% |