Find Cheap Flights from Caribbean to Chicago O'Hare International

Search hundreds of travel sites at once for deals on flights to Chicago O'Hare International

Thu 1/18
Thu 1/25
Any month
Compare vs. KAYAK |

Book cheap flights from Caribbean to Chicago O'Hare International (round-trip)

Airports
Origin
Aguadilla
$218
only
$218
San Juan
$231
only
$231
Punta Cana
$286
only
$286
Destination
Chicago
$218
only
$218
Thu, Apr 19
BQN
ORD
8h 50m
Thu, May 3
ORD
BQN
8h 29m
Trip: 15 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52049 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
FLL
LGA
Okay 4.0

The fact that this company can't even provide FREE water

MYR
LGA
Mediocre 3.6

The staff was friendly

The lack of proper information about Luggage policy end pricing.

FLL
EWR
Mediocre 3.3

Got to Newark late but safe

Everything

LAX
ORD
Good 7.3

No delays, no baggage issues. Everything but food and entertainment (cant rate on those because there was none), was 5 out of 5.

No complaint available.

IAH
MCO
Mediocre 2.0

My flight was delayed and then cancelled after we waited for 2 hours after boarding the plane.

Tue, Jan 30
SJU
ORD
8h 14m
Tue, Feb 6
ORD
SJU
10h 24m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Feb 21
SJU
ORD
6h 47m
Tue, Feb 27
ORD
SJU
10h 20m
Trip: 7 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 4 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
FLL
DTW
Good 7.6

The entertainment device failed to work. . Screen crashed .

JFK
TPA
Excellent 8.0

My child had a very good escorted flight the attendants were very attentive and knowledgeable of my child's needs I highly recommend and if anyone needs an escorted flight they definitely will not regret it

All was good

JFK
LAX
Excellent 10.0

Food and drink provided on flight. That's amazing!

Nothing :)

SEA
JFK
Good 7.3

crew very unfriemdly

FLL
BOS
Mediocre 2.0

Nothing

Overhead reading lights didn’t work, my partners tv didn’t work, the movie I had was only in Spanish and the overhead bins were too small and had to gate check my bag Sloppy plane maintenance by JetBlue Not worth the extra money to sit in extra leg room seats over$120 for two of us

Wed, Feb 28
PUJ
ORD
5h 10m
Tue, Mar 6
ORD
PUJ
4h 35m
Trip: 7 days
6.7GoodShow reviews
Overall 6.7 Good
Based on 9 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
PUJ
ORD
Excellent 9.6

Boarding the plane from the ground using both the front and rear doors of the plane made loading carryon luggage much better than airports that use an enclosed extended arm for only the front door. The extra leg room for sitting in an exit row with reclining capability is huge! I would be willing to pay to get an exit row all the time since the first flight was spent in a "normal" seat and the leg room is pretty bad with how many rows of non-reclining seats have been crammed into their planes.

The open access to the planes required extra security personal constantly checking passports and boarding passes because there's the possibility of wandering over and boarding an incorrect plane.

MIA
LGA
Mediocre 2.0

if you have a hard engagement that you have to make, i hate to say it, but use a bigger airline. These guys are not dependable nyc -> miami. Have had 2 flights cancelled and delayed over 6 hours in the last 6 months. Only one scheduled flight everyday. If you can risk it, fine, but otherwise not worth it.

PUJ
ORD
Excellent 9.3

The flight was late in boarding because the airport was on island time. The reception folks kept saying five more minutes until we board, for like half an hour. I didn't mind but it was funny. A very relaxed airport and staff. I enjoyed it, way better than O'Hare with its rushing hussle bussle endless security line issues.

PUJ
ORD
Okay 4.0

I paid for my flight but when I tried to check in, I had to pay for my seat and carry on for each way. Orange juice costs money on this flight. Seats are half of the size of regular seats and does not recline. It was like sitting in school room chairs for 4 hours and 37 minutes on a full flight. Water is the only thing that you can have without paying. I just didn't understand what I paid for... when I also had to pay for a seat. Was it the cost of fuel on the aircraft? Trays are half of the size of regular tray... custom forms barely fit on top of it. Brace position is not going to do anything to us with those plastic seats in case of emergency.

ATL
LAS
Good 6.0

The crew was very friendly.

The seats were close together and not very comfortable. No entertainment, for example a movie for a 4 hour flight. You have to pay for everything. Only thing complimentary is water.

Tue, Apr 24
BQN
ORD
8h 50m
Thu, May 3
ORD
BQN
8h 29m
Trip: 10 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52049 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
RSW
ORD
Mediocre 3.6

They downsized the plan and couldn't fly out to much later that day

FLL
EWR
Mediocre 3.3

Got to Newark late but safe

Everything

MCO
BOS
Excellent 9.6

good flight, excellent service

food prices

LAX
ATL
Excellent 8.0

It was cheap

Very small seats. Good for a short flight but not so much LAX to ATL.

BWI
SEA
Okay 4.6

Dirty Seat doesn’t recline Seat doesn’t have head support on sides No movies No phone charger Small food tray Poor food choice No free water

Wed, Jan 31
SJU
ORD
8h 14m
Wed, Feb 7
ORD
SJU
10h 24m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Apr 25
BQN
ORD
7h 13m
Thu, May 3
ORD
BQN
8h 29m
Trip: 9 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52049 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAX
ORD
Good 7.3

No delays, no baggage issues. Everything but food and entertainment (cant rate on those because there was none), was 5 out of 5.

No complaint available.

IAH
MCO
Mediocre 2.0

My flight was delayed and then cancelled after we waited for 2 hours after boarding the plane.

ORD
LAX
Good 7.3

Can only rate on everything but Entertainment & Food, since there was neither of those. Other than those it was 5 Stars all around.

No complaints available.

BWI
SEA
Okay 4.6

Dirty Seat doesn’t recline Seat doesn’t have head support on sides No movies No phone charger Small food tray Poor food choice No free water

LAX
ATL
Excellent 8.0

It was cheap

Very small seats. Good for a short flight but not so much LAX to ATL.

Tue, Feb 13
SJU
ORD
8h 14m
Tue, Feb 27
ORD
SJU
10h 20m
Trip: 15 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Feb 22
SJU
ORD
6h 47m
Tue, Feb 27
ORD
SJU
10h 20m
Trip: 6 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 4 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
JFK
SAN
Excellent 10.0

Great plane, Clean and looked in great and good condition. Seats were good so my back wasn't hurting after 5 hours. Great movies, snacks, drinks, and lighting in the plane.

Perfect flight.

SEA
JFK
Good 7.3

crew very unfriemdly

BNA
FLL
Good 7.0

Every single employee I interacted with was awesome.

Over 5 hours in delay due to a maintenance issue. Problem wasn't discovered overnight when it was parked. Wasn't discovered until the next day. Had to wait for the delivery of a specific part and install it. I'm all for planes not breaking upon reentry, but the fact that the two flights were both subsequently delayed 4-5 hours each instead of bringing in a sub plane was inconsiderate. Now I've got a long drive home and I'll only get an hour of sleep before a 14-hour work day. So thanks for that, JetBlue

JFK
SDQ
Excellent 10.0

Todo bien y muy rápido

FLL
BOS
Mediocre 2.0

Nothing

Overhead reading lights didn’t work, my partners tv didn’t work, the movie I had was only in Spanish and the overhead bins were too small and had to gate check my bag Sloppy plane maintenance by JetBlue Not worth the extra money to sit in extra leg room seats over$120 for two of us

Sun, Mar 11
BQN
ORD
9h 07m
Mon, Mar 19
ORD
BQN
6h 29m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52049 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
RSW
ORD
Mediocre 3.6

They downsized the plan and couldn't fly out to much later that day

FLL
LGA
Okay 4.0

The fact that this company can't even provide FREE water

IAH
MCO
Mediocre 2.0

My flight was delayed and then cancelled after we waited for 2 hours after boarding the plane.

LAX
ATL
Excellent 8.0

It was cheap

Very small seats. Good for a short flight but not so much LAX to ATL.

FLL
EWR
Mediocre 3.3

Got to Newark late but safe

Everything

Thu, Feb 1
SJU
ORD
9h 46m
Wed, Feb 7
ORD
SJU
10h 24m
Trip: 7 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 4 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
JFK
SDQ
Excellent 10.0

Todo bien y muy rápido

BNA
FLL
Good 7.0

Every single employee I interacted with was awesome.

Over 5 hours in delay due to a maintenance issue. Problem wasn't discovered overnight when it was parked. Wasn't discovered until the next day. Had to wait for the delivery of a specific part and install it. I'm all for planes not breaking upon reentry, but the fact that the two flights were both subsequently delayed 4-5 hours each instead of bringing in a sub plane was inconsiderate. Now I've got a long drive home and I'll only get an hour of sleep before a 14-hour work day. So thanks for that, JetBlue

DCA
FLL
Excellent 8.0

The plane was 30+ minutes late arriving at the gate to load. The lavatory at the rear of the plane was out of order. Otherwise the flight was smooth and the attendants excellent.

FLL
BOS
Mediocre 2.0

Nothing

Overhead reading lights didn’t work, my partners tv didn’t work, the movie I had was only in Spanish and the overhead bins were too small and had to gate check my bag Sloppy plane maintenance by JetBlue Not worth the extra money to sit in extra leg room seats over$120 for two of us

JFK
LAX
Excellent 10.0

Food and drink provided on flight. That's amazing!

Nothing :)

Wed, Feb 14
SJU
ORD
8h 14m
Wed, Feb 28
ORD
SJU
14h 40m
Trip: 15 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jan 30
SJU
ORD
8h 14m
Wed, Feb 7
ORD
SJU
6h 57m
Trip: 9 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52049 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAX
ORD
Good 7.3

No delays, no baggage issues. Everything but food and entertainment (cant rate on those because there was none), was 5 out of 5.

No complaint available.

FLL
LGA
Okay 4.0

The fact that this company can't even provide FREE water

MYR
LGA
Mediocre 3.6

The staff was friendly

The lack of proper information about Luggage policy end pricing.

MCO
BOS
Excellent 9.6

good flight, excellent service

food prices

ORD
LAX
Good 7.3

Can only rate on everything but Entertainment & Food, since there was neither of those. Other than those it was 5 Stars all around.

No complaints available.

Thu, Feb 1
SJU
ORD
9h 46m
Thu, Feb 8
ORD
SJU
6h 57m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Feb 2
SJU
ORD
8h 00m
Tue, Feb 6
ORD
SJU
10h 24m
Trip: 5 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 4 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
BNA
FLL
Good 7.0

Every single employee I interacted with was awesome.

Over 5 hours in delay due to a maintenance issue. Problem wasn't discovered overnight when it was parked. Wasn't discovered until the next day. Had to wait for the delivery of a specific part and install it. I'm all for planes not breaking upon reentry, but the fact that the two flights were both subsequently delayed 4-5 hours each instead of bringing in a sub plane was inconsiderate. Now I've got a long drive home and I'll only get an hour of sleep before a 14-hour work day. So thanks for that, JetBlue

FLL
DTW
Good 7.6

The entertainment device failed to work. . Screen crashed .

JFK
SAN
Excellent 10.0

Great plane, Clean and looked in great and good condition. Seats were good so my back wasn't hurting after 5 hours. Great movies, snacks, drinks, and lighting in the plane.

Perfect flight.

JFK
LAX
Excellent 10.0

Food and drink provided on flight. That's amazing!

Nothing :)

ORD
BOS
Good 6.0

Turbulence was terrible, understand that is not JetBlue issue - wanted to note.

Wed, Jan 31
SJU
ORD
8h 14m
Wed, Feb 7
ORD
SJU
6h 57m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52049 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
MYR
LGA
Mediocre 3.6

The staff was friendly

The lack of proper information about Luggage policy end pricing.

LAX
ORD
Good 7.3

No delays, no baggage issues. Everything but food and entertainment (cant rate on those because there was none), was 5 out of 5.

No complaint available.

ORD
LAX
Good 7.3

Can only rate on everything but Entertainment & Food, since there was neither of those. Other than those it was 5 Stars all around.

No complaints available.

BWI
SEA
Okay 4.6

Dirty Seat doesn’t recline Seat doesn’t have head support on sides No movies No phone charger Small food tray Poor food choice No free water

FLL
EWR
Mediocre 3.3

Got to Newark late but safe

Everything

Thu, Feb 1
SJU
ORD
8h 14m
Mon, Feb 12
ORD
SJU
22h 25m
Trip: 12 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Feb 3
SJU
ORD
8h 00m
Wed, Feb 7
ORD
SJU
10h 24m
Trip: 5 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 4 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
JFK
TPA
Excellent 8.0

My child had a very good escorted flight the attendants were very attentive and knowledgeable of my child's needs I highly recommend and if anyone needs an escorted flight they definitely will not regret it

All was good

SEA
JFK
Good 7.3

crew very unfriemdly

JFK
LAX
Excellent 10.0

Food and drink provided on flight. That's amazing!

Nothing :)

FLL
BOS
Mediocre 2.0

Nothing

Overhead reading lights didn’t work, my partners tv didn’t work, the movie I had was only in Spanish and the overhead bins were too small and had to gate check my bag Sloppy plane maintenance by JetBlue Not worth the extra money to sit in extra leg room seats over$120 for two of us

PBI
HPN
Excellent 10.0

Up to expectation; on time, smooth check in with kiosk, efficient and courteous TSA security line, clear navigational sign, bookstore, clean windows, clean seat, and clean air.

waiting area after security checkpoint is a little too tight at West Palm Beach International Airport.

Thu, Feb 1
SJU
ORD
8h 14m
Wed, Feb 7
ORD
SJU
6h 57m
Trip: 7 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52049 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
MCO
BWI
Okay 4.6

Dirty Seat doesn’t recline Seat doesn’t have head support on sides No movies No phone charger Small food tray Poor food choice No free water

LAX
ORD
Good 7.3

No delays, no baggage issues. Everything but food and entertainment (cant rate on those because there was none), was 5 out of 5.

No complaint available.

BWI
SEA
Okay 4.6

Dirty Seat doesn’t recline Seat doesn’t have head support on sides No movies No phone charger Small food tray Poor food choice No free water

BOS
MCO
Excellent 9.6

good trip, excellent service

food prices

IAH
MCO
Mediocre 2.0

My flight was delayed and then cancelled after we waited for 2 hours after boarding the plane.

Mon, Feb 5
SJU
ORD
19h 20m
Tue, Feb 13
ORD
SJU
17h 47m
Trip: 9 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52049 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAX
ATL
Excellent 8.0

It was cheap

Very small seats. Good for a short flight but not so much LAX to ATL.

MYR
LGA
Mediocre 3.6

The staff was friendly

The lack of proper information about Luggage policy end pricing.

MCO
BWI
Okay 4.6

Dirty Seat doesn’t recline Seat doesn’t have head support on sides No movies No phone charger Small food tray Poor food choice No free water

FLL
EWR
Mediocre 3.3

Got to Newark late but safe

Everything

ORD
LAX
Good 7.3

Can only rate on everything but Entertainment & Food, since there was neither of those. Other than those it was 5 Stars all around.

No complaints available.

Caribbean to Chicago O'Hare International Flight Information

Flights Arrive in Chicago O'Hare International
Flights Depart from Caribbean
Flight Price $218
Airlines Spirit Airlines, JetBlue, Frontier
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.