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
$133 - $292
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
Nonstop4h 59m
Chicago O'Hare Intl
Wed 9/11
1 stop6h 45m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 9/10
Nonstop4h 59m
Chicago O'Hare Intl
Wed 9/11
Nonstop4h 47m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 7/2
1 stop9h 29m
Chicago O'Hare Intl
Tue 7/9
1 stop14h 41m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 9/10
Nonstop4h 59m
Chicago O'Hare Intl
Tue 9/17
1 stop12h 49m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 9/10
1 stop15h 16m
Chicago O'Hare Intl
Tue 9/17
1 stop12h 49m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 7/25
1 stop8h 42m
Chicago O'Hare Intl
Thu 8/8
1 stop10h 05m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 6/19
1 stop13h 23m
Chicago O'Hare Intl
Wed 7/17
Nonstop4h 49m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sun 6/30
1 stop22h 57m
Chicago O'Hare Intl
Mon 7/8
1 stop6h 23m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 9/10
2 stops10h 30m
Chicago O'Hare Intl
Wed 9/11
2 stops8h 59m
No data available for this route at this time. Please check back soon.
Overall
Comfort
Entertainment
Boarding
Crew
Food
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.
Overall
Comfort
Entertainment
Boarding
Crew
Food
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.
Overall
Comfort
Entertainment
Boarding
Crew
Food
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.
Overall
Comfort
Entertainment
Boarding
Crew
Food
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.
Overall
Comfort
Entertainment
Boarding
Crew
Food
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.
Overall
Comfort
Entertainment
Boarding
Crew
Food
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.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Spirit Airlines | Cheapest$112 | Average$348 | FlexibilityNo cancel fee | On-time65% |
Frontier | Cheapest$114 | Average$272 | FlexibilityNo cancel fee | On-time62% |
United Airlines | Cheapest$149 | Average$513 | FlexibilityNo cancel fee | On-time69% |
Delta | Cheapest$160 | Average$474 | FlexibilityNo cancel fee | On-timeN/A |
JetBlue | Cheapest$168 | Average$310 | FlexibilityNo cancel fee | On-time62% |
American Airlines | Cheapest$279 | Average$538 | FlexibilityNo cancel fee | On-time71% |
Copa Airlines | Cheapest$359 | Average$568 | FlexibilityNo cancel fee | On-time70% |
10%of flight departures | Early morningMidnight to 6 am |
---|---|
9%of flight departures | Morning6 am to noon |
81%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |