Round-trip from | $218 (Spirit) |
---|---|
One-way from | $114 (Priceline) |
Popular in | December |
Cheapest in | September |
Average price | $385 |
Good round-trip deal | $260 or less |
Good one-way deal | $146 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 8/3
6:23 pm-12:06 am
Nonstop4h 43m
San Juan Luis Munoz Marin Intl
Fri 8/8
3:50 pm-7:04 am
1 stop16h 14m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 8/18
6:20 am-2:18 pm
1 stop6h 58m
San Juan Luis Munoz Marin Intl
Fri 8/22
3:21 pm-11:27 pm
1 stop9h 06m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 8/11
7:45 am-4:43 pm
1 stop7h 58m
San Juan Luis Munoz Marin Intl
Thu 8/21
7:25 am-6:28 pm
1 stop12h 03m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 9/16
10:35 am-10:00 pm
1 stop10h 25m
San Juan Luis Munoz Marin Intl
Fri 9/19
12:58 pm-9:36 pm
1 stop9h 38m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 9/8
7:00 am-4:27 pm
1 stop8h 27m
San Juan Luis Munoz Marin Intl
Sat 9/13
7:30 am-4:31 pm
1 stop10h 01m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 8/25
10:26 am-9:48 pm
1 stop10h 22m
San Juan Luis Munoz Marin Intl
Sat 8/30
3:21 pm-11:33 pm
1 stop9h 12m
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Mon 8/18
6:56 am-3:19 pm
1 stop7h 23m
Saint Thomas Island Cyril E King
Mon 8/25
2:43 pm-10:22 pm
1 stop8h 39m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sat 8/23
5:05 am-3:00 pm
1 stop8h 55m
Punta Cana
Wed 8/27
4:05 pm-11:59 pm
1 stop8h 54m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Tue 8/5
6:45 am-12:25 pm
Nonstop4h 40m
Punta Cana
Wed 8/13
5:08 pm-9:16 pm
Nonstop5h 08m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 8/11
6:45 am-12:25 pm
Nonstop4h 40m
Punta Cana
Wed 8/20
4:05 pm-11:59 pm
1 stop8h 54m
Currently, September is the cheapest month in which you can book a flight from Illinois to Caribbean (average of $254). Flying from Illinois to Caribbean in June is currently the most expensive (average of $339). 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.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Caribbean as you normally would.
The most flights from USIL 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).
Crew
Overall
Food
Boarding
Comfort
Entertainment
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Food
Boarding
Comfort
Entertainment
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Food
Boarding
Comfort
Entertainment
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Food
Boarding
Comfort
Entertainment
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Food
Boarding
Comfort
Entertainment
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Food
Boarding
Comfort
Entertainment
Reviews
John,May 2025
PVD - BNA
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$106 | Average$357 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$139 | Average$378 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$193 | Average$536 | FlexibilityNo cancel fee | On-time70% | |
Cheapest$194 | Average$656 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$216 | Average$617 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$226 | Average$667 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$234 | Average$313 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$261 | Average$481 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$335 | Average$750 | FlexibilityNo cancel fee | On-time67% | |
Cheapest$352 | Average$649 | FlexibilityNo cancel fee | On-time63% |