To save on the cost of your flight from Caribbean to Illinois, book at least 16 days before your planned departure. Booking around this time can save you about 85% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $238 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $311.
Flights from Caribbean to Illinois lean towards being more expensive in March. Prices are generally better when you fly from Caribbean to Illinois in January, with the cheapest ticket starting at $122.
When flying from Caribbean to Illinois, 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
$144 - $342
Route
Depart
Return
Price
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 6/5
1 stop13h 55m
Chicago O'Hare Intl
Tue 7/16
1 stop10h 33m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 6/4
2 stops29h 54m
Chicago O'Hare Intl
Tue 7/16
1 stop10h 33m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 6/4
Nonstop5h 10m
Chicago O'Hare Intl
Tue 7/16
1 stop10h 33m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 6/5
1 stop21h 23m
Chicago O'Hare Intl
Tue 6/11
1 stop10h 19m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 6/5
1 stop13h 55m
Chicago O'Hare Intl
Sat 6/22
2 stops15h 40m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 6/5
1 stop7h 23m
Chicago Midway
Mon 6/10
1 stop12h 01m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 8/8
1 stop9h 06m
Chicago O'Hare Intl
Sun 8/11
1 stop8h 33m
Punta CanaChicago O'Hare Intl
PUJ - ORD
PUJORD
Punta Cana
Thu 10/24
1 stop7h 39m
Chicago O'Hare Intl
Mon 10/28
Nonstop4h 28m
Nassau IntlChicago O'Hare Intl
NAS - ORD
NASORD
Nassau Intl
Wed 6/5
2 stops14h 51m
Chicago O'Hare Intl
Tue 6/11
1 stop6h 55m
No data available for this route at this time. Please check back soon.
Entertainment
Food
Overall
Crew
Boarding
Comfort
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Entertainment
Food
Overall
Crew
Boarding
Comfort
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Entertainment
Food
Overall
Crew
Boarding
Comfort
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Entertainment
Food
Overall
Crew
Boarding
Comfort
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Entertainment
Food
Overall
Crew
Boarding
Comfort
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Entertainment
Food
Overall
Crew
Boarding
Comfort
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
10%of flight departures | Early morningMidnight to 6 am |
---|---|
21%of flight departures | Morning6 am to noon |
69%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
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