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
$135 - $357
Route
Depart
Return
Price
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 9/10
1 stop10h 28m
Chicago O'Hare Intl
Tue 9/24
1 stop7h 38m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 6/5
1 stop14h 55m
Chicago O'Hare Intl
Tue 6/25
1 stop10h 29m
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 6/25
1 stop10h 29m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 5/28
2 stops29h 13m
Chicago O'Hare Intl
Wed 5/29
1 stop27h 00m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 5/28
2 stops29h 13m
Chicago O'Hare Intl
Sat 6/1
1 stop8h 40m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 6/3
1 stop9h 53m
Chicago Midway
Mon 6/10
1 stop17h 41m
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 stops16h 31m
Chicago O'Hare Intl
Tue 6/11
1 stop6h 40m
Montego Bay Sangster IntlChicago O'Hare Intl
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Wed 7/10
Nonstop4h 30m
Chicago O'Hare Intl
Wed 8/28
Nonstop4h 00m
No data available for this route at this time. Please check back soon.
Crew
Food
Overall
Boarding
Comfort
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Food
Overall
Boarding
Comfort
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Food
Overall
Boarding
Comfort
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Food
Overall
Boarding
Comfort
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Food
Overall
Boarding
Comfort
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Food
Overall
Boarding
Comfort
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
7%of flight departures | Early morningMidnight to 6 am |
---|---|
8%of flight departures | Morning6 am to noon |
85%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
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