Find a great deal and save up to 85% by booking at least 16 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 Caribbean to Chicago O'Hare Intl Airport within the next two weeks, with the cheapest ticket starting at $238.
January can be a great time to fly to Chicago O'Hare Intl Airport from Caribbean with a flight ticket averaging about $270. Cheapflights users have found deals in the month of January for as cheap as $122. The most expensive prices can be found in the month of March.
When flying from Caribbean to Chicago O'Hare Intl Airport, 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 O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 5/28
1 stop10h 22m
Chicago O'Hare Intl
Thu 6/20
1 stop9h 17m
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
Sun 8/4
Nonstop4h 30m
Chicago O'Hare Intl
Sat 8/17
Nonstop4h 00m
No data available for this route at this time. Please check back soon.
Boarding
Crew
Comfort
Entertainment
Food
Overall
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.
Boarding
Crew
Comfort
Entertainment
Food
Overall
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.
Boarding
Crew
Comfort
Entertainment
Food
Overall
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.
Boarding
Crew
Comfort
Entertainment
Food
Overall
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.
Boarding
Crew
Comfort
Entertainment
Food
Overall
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.
Boarding
Crew
Comfort
Entertainment
Food
Overall
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.
5%of flight departures | Early morningMidnight to 6 am |
---|---|
6%of flight departures | Morning6 am to noon |
89%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
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