Find a great deal and save up to 20% by booking at least 57 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Illinois to Caribbean within the next two weeks, with the cheapest ticket starting at $258.
The best pricing can be found in the month of October. Prices to Caribbean from Illinois average $318. You can even find prices in October for less than $318, as users have found deals to Caribbean from as low as $90. The month of March appears to be one of the more expensive times to travel to Caribbean from Illinois. Flying in the targeted month can save you up to 60%.
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.
Fly from
Fly to
Budget
$120 - $283
Route
Depart
Return
Price
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/21
1 stop13h 11m
San Juan Luis Munoz Marin Intl
Sat 5/25
1 stop9h 00m
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
Tue 5/21
2 stops23h 36m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/21
1 stop7h 13m
San Juan Luis Munoz Marin Intl
Sat 5/25
1 stop8h 01m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 6/4
1 stop17h 00m
San Juan Luis Munoz Marin Intl
Sat 6/8
1 stop8h 21m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sat 5/18
1 stop10h 15m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop16h 05m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 5/21
1 stop12h 38m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop16h 05m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Mon 5/20
1 stop6h 28m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop16h 05m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/18
1 stop13h 27m
San Juan Luis Munoz Marin Intl
Sat 5/25
1 stop8h 01m
Chicago O'Hare IntlPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 5/19
1 stop15h 30m
Punta Cana
Thu 5/23
Nonstop5h 05m
No data available for this route at this time. Please check back soon.
Comfort
Entertainment
Boarding
Crew
Overall
Food
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Comfort
Entertainment
Boarding
Crew
Overall
Food
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Comfort
Entertainment
Boarding
Crew
Overall
Food
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Comfort
Entertainment
Boarding
Crew
Overall
Food
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Comfort
Entertainment
Boarding
Crew
Overall
Food
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Comfort
Entertainment
Boarding
Crew
Overall
Food
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
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 |
900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Caribbean from Illinois today with Cheapflights!
Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Illinois to Caribbean for you. Better yet — we are completely free to use.
Cheapflights does show flights with no change fees to all users. To see these options for flights from Illinois to Caribbean, users can toggle the no change fees filter when performing a flight search.
Yes! Start tracking prices for Illinois to Caribbean flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.