Round-trip from | $180 (eDestinos) |
---|---|
One-way from | $81 (Cheapflightsfares) |
Popular in | December |
Cheapest in | August |
Average price | $430 |
Good round-trip deal | $266 or less |
Good one-way deal | $151 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 4/23
8:04 am-1:45 pm
Nonstop4h 41m
San Juan Luis Munoz Marin Intl
Wed 4/30
6:35 am-10:58 am
Nonstop5h 23m
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Fri 5/2
7:47 pm-10:00 am
1 stop13h 13m
Saint Thomas Island Cyril E King
Sat 5/10
10:52 am-12:24 am
1 stop14h 32m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 4/17
8:10 am-8:19 pm
1 stop11h 09m
San Juan Luis Munoz Marin Intl
Thu 4/24
6:35 am-10:58 am
Nonstop5h 23m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 4/7
9:50 am-6:28 pm
1 stop7h 38m
San Juan Luis Munoz Marin Intl
Tue 4/8
2:55 am-10:40 am
1 stop8h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 4/25
6:15 am-3:22 pm
1 stop8h 07m
San Juan Luis Munoz Marin Intl
Fri 5/2
6:00 am-5:28 pm
1 stop12h 28m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Wed 7/16
5:15 am-2:00 pm
1 stop7h 45m
Punta Cana
Sun 7/20
4:55 pm-11:57 pm
1 stop8h 02m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 5/11
4:15 pm-2:17 pm
2 stops21h 02m
Punta Cana
Thu 5/15
5:54 pm-10:00 pm
Nonstop5h 06m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 4/26
1:26 pm-10:02 pm
1 stop7h 36m
San Juan Luis Munoz Marin Intl
Tue 4/29
3:28 am-12:13 pm
1 stop9h 45m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 5/11
5:05 am-2:17 pm
1 stop8h 12m
Punta Cana
Thu 5/15
12:42 pm-8:03 pm
1 stop8h 21m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sat 4/26
6:20 am-11:56 am
Nonstop4h 36m
Punta Cana
Tue 4/29
5:50 pm-10:08 pm
Nonstop5h 18m
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 Thursday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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).
Comfort
Crew
Food
Boarding
Entertainment
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Comfort
Crew
Food
Boarding
Entertainment
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Comfort
Crew
Food
Boarding
Entertainment
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Comfort
Crew
Food
Boarding
Entertainment
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Comfort
Crew
Food
Boarding
Entertainment
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Comfort
Crew
Food
Boarding
Entertainment
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$124 | Average$352 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$144 | Average$339 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$193 | Average$540 | FlexibilityNo cancel fee | On-time70% | |
Cheapest$226 | Average$641 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$235 | Average$660 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$293 | Average$510 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$332 | Average$637 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$335 | Average$779 | FlexibilityNo cancel fee | On-time67% | |
Cheapest$342 | Average$680 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$397 | Average$953 | FlexibilityNo cancel fee | On-time71% |