Find Cheap Flights from Caribbean to Chicago O'Hare International

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

Airports
Origin
Aguadilla
$272
only
$272
Nassau
$306
only
$306
San Juan
$188
only
$188
Montego Bay
$349
only
$349
Destination
Chicago
$188
only
$188
Wed, Jan 10
SJU
ORD
6h 53m
Tue, Jan 23
ORD
SJU
6h 56m
Trip: 14 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ATL
MSY
Excellent 10.0

I've got a lot of travel bags. None are the "personal" size you demand. The bag I used, was actually overall smaller than required, though one dimension was 1 inch to wide to fit in the box. The Gate Attendant said it was no problem. My concern is what the next Attendant say? Your baggage prices are too high!

The price for the trip in the large front seats! I'm a big guy.

MCO
MSY
Mediocre 3.3

My flight being short

Paying $90 for having one piece of carry on. Not having the option to even pay for WiFi as it’s nonexistent on Spirit’s planes.

FLL
IAH
Mediocre 3.0

They moved us from the gate to have an "on-time" departure even though we sat on the taxi way for a while. Why do airlines do this? Are on time stats more important than customer comfort and satisfaction. Then they kept the lights on during the entire flight to "sell" their products. Please, give us at least a free glass of water. You are only cheaper than other airlines when you get a $9 fare, which you have to pay to have anyhow. So they are a bare bone airline, but charges are for everything. This airline stinks, I will not be flying them again unless I absolutely have to. I thought United was bad, but they are great compared to Spirit.

LAS
CLE
Excellent 10.0

zero problems

all great

MSY
BWI
Mediocre 2.0

Small seats

Wed, Jan 10
SJU
ORD
31h 18m
Thu, Jan 25
ORD
SJU
7h 10m
Trip: 16 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Dec 16
NAS
ORD
3h 50m
Wed, Jan 3
ORD
NAS
14h 41m
Trip: 19 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 4 reviews
Overall
7.2
Boarding
7.3
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
NAS
ORD
Excellent 10.0

Flight down was without delay and comfortable

Flight back was delayed due to a comedy of errors with Bahama over uploading potable water.

SJC
EWR
Mediocre 3.6

Arrived on time

Narrow seat

LAX
ORD
Good 7.3

The crew was excellent

The seating space is to small

EWR
NRT
Mediocre 3.6

There was a flight attendant who was a little rude.

FAT
DEN
Excellent 8.0

Heavy Hispanic woman got ill and I was really worried she might pass away because she kept laying forward asleep or passed out on the back of the seat in front of her. Finally they found a doctor who was bilingual and he took great care of her. So bravo for that UA!

Heavy Hispanic woman got ill and I was really worried she might pass away because she kept laying forward asleep or passed out on the back of the seat in front of her. Finally they found a doctor who was bilingual and he took great care of her. So bravo for that UA!

Wed, Jan 17
SJU
ORD
8h 16m
Wed, Jan 24
ORD
SJU
6h 56m
Trip: 8 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PAP
FLL
Good 7.0

My flight was very smooth, you get very pilot

I have to pay so much for my luggage. .when I get at the airport, it was my time with the spirit air lines....

LGA
FLL
Okay 4.6

Flight was delayed. They charged for carryon bags, they charged for water.

IAH
LAS
Mediocre 3.0

Nothing to like really. Crew gathered in galley area, eating & drinking. Crew did not attend to passengers who were swinging feet & legs out in the aisle, pick up trash or other.

See above.///////////////////////////////////////////

MCO
MSY
Mediocre 3.3

My flight being short

Paying $90 for having one piece of carry on. Not having the option to even pay for WiFi as it’s nonexistent on Spirit’s planes.

LAS
PDX
Mediocre 3.0

Hey, nothing is free. Not even water. So don't buzz through the aisle saying "food & drinks for purchase", no one's buying. Or "you can move up to a roomier seat for $75." instead of marketing that expensive seat, just get this sjow on the road. I just paid $50 to send a carry-on piece of luggage. Nickle-dime ppl to death!

See above!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!////////////////////////

Mon, Dec 25
SJU
ORD
5h 29m
Mon, Jan 1
ORD
SJU
4h 33m
Trip: 8 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 11 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
SJU
ORD
Good 7.3

Todo muy bueno

PWM
PHL
Okay 4.6

We arrived on time.

These planes feel like they are made of Legos. They are absurdly tiny and uncomfortable (and I am a small woman). Hot and stinky when boarding and no room for you or your carry on luggage. The days of glamorous air travel seem very far away.

CHO
ORD
Good 7.6

It was a little hot in the plane at during start and touchdown

MBJ
PHL
Excellent 8.6

AA flight was relaxed and smooth, crew was respectful and warm can’t think

Can’t think of anything I didn’t like

BDL
CLT
Okay 4.0

No baggage controls from seat 18 to 28 no bags would fit. As we exited all the front rows we're waiting to get there bags stored in back of planes overhead bins. That's just not right, especially when they charge us extra to take a bag for overhead bins storage.

Tue, Jan 23
SJU
ORD
8h 16m
Tue, Jan 30
ORD
SJU
6h 56m
Trip: 8 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
IAH
LAS
Mediocre 3.0

Nothing to like really. Crew gathered in galley area, eating & drinking. Crew did not attend to passengers who were swinging feet & legs out in the aisle, pick up trash or other.

See above.///////////////////////////////////////////

LGA
FLL
Okay 4.6

Flight was delayed. They charged for carryon bags, they charged for water.

LAX
DTW
Excellent 10.0

Excellent experience as always. The young crew were very nice and energetic and helpful, I am always happy flying with Spirit.

Nothing.

LAS
PDX
Mediocre 3.0

Hey, nothing is free. Not even water. So don't buzz through the aisle saying "food & drinks for purchase", no one's buying. Or "you can move up to a roomier seat for $75." instead of marketing that expensive seat, just get this sjow on the road. I just paid $50 to send a carry-on piece of luggage. Nickle-dime ppl to death!

See above!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!////////////////////////

MCO
MSY
Mediocre 3.3

My flight being short

Paying $90 for having one piece of carry on. Not having the option to even pay for WiFi as it’s nonexistent on Spirit’s planes.

Wed, Feb 21
SJU
ORD
8h 38m
Tue, Feb 27
ORD
SJU
6h 51m
Trip: 7 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
MCO
MSY
Mediocre 3.3

My flight being short

Paying $90 for having one piece of carry on. Not having the option to even pay for WiFi as it’s nonexistent on Spirit’s planes.

LAX
DTW
Excellent 10.0

Excellent experience as always. The young crew were very nice and energetic and helpful, I am always happy flying with Spirit.

Nothing.

ATL
MSY
Excellent 10.0

I've got a lot of travel bags. None are the "personal" size you demand. The bag I used, was actually overall smaller than required, though one dimension was 1 inch to wide to fit in the box. The Gate Attendant said it was no problem. My concern is what the next Attendant say? Your baggage prices are too high!

The price for the trip in the large front seats! I'm a big guy.

LAS
CLE
Excellent 10.0

zero problems

all great

MSY
BWI
Mediocre 2.0

Small seats

Thu, Feb 22
SJU
ORD
8h 38m
Wed, Feb 28
ORD
SJU
6h 51m
Trip: 7 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
IAH
LAS
Mediocre 3.0

Nothing to like really. Crew gathered in galley area, eating & drinking. Crew did not attend to passengers who were swinging feet & legs out in the aisle, pick up trash or other.

See above.///////////////////////////////////////////

MCO
MSY
Mediocre 3.3

My flight being short

Paying $90 for having one piece of carry on. Not having the option to even pay for WiFi as it’s nonexistent on Spirit’s planes.

MSY
BWI
Mediocre 2.0

Small seats

FLL
IAH
Mediocre 3.0

They moved us from the gate to have an "on-time" departure even though we sat on the taxi way for a while. Why do airlines do this? Are on time stats more important than customer comfort and satisfaction. Then they kept the lights on during the entire flight to "sell" their products. Please, give us at least a free glass of water. You are only cheaper than other airlines when you get a $9 fare, which you have to pay to have anyhow. So they are a bare bone airline, but charges are for everything. This airline stinks, I will not be flying them again unless I absolutely have to. I thought United was bad, but they are great compared to Spirit.

LGA
FLL
Okay 4.6

Flight was delayed. They charged for carryon bags, they charged for water.

Mon, Mar 12
BQN
ORD
8h 43m
Mon, Mar 19
ORD
BQN
18h 12m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Feb 22
SJU
ORD
8h 38m
Wed, Feb 28
ORD
SJU
6h 51m
Trip: 7 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ATL
MSY
Excellent 10.0

I've got a lot of travel bags. None are the "personal" size you demand. The bag I used, was actually overall smaller than required, though one dimension was 1 inch to wide to fit in the box. The Gate Attendant said it was no problem. My concern is what the next Attendant say? Your baggage prices are too high!

The price for the trip in the large front seats! I'm a big guy.

LAS
PDX
Mediocre 3.0

Hey, nothing is free. Not even water. So don't buzz through the aisle saying "food & drinks for purchase", no one's buying. Or "you can move up to a roomier seat for $75." instead of marketing that expensive seat, just get this sjow on the road. I just paid $50 to send a carry-on piece of luggage. Nickle-dime ppl to death!

See above!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!////////////////////////

LGA
FLL
Okay 4.6

Flight was delayed. They charged for carryon bags, they charged for water.

FLL
LGA
Okay 5.3

Nice professional crew.

No movies.

IAH
LAS
Mediocre 3.0

Nothing to like really. Crew gathered in galley area, eating & drinking. Crew did not attend to passengers who were swinging feet & legs out in the aisle, pick up trash or other.

See above.///////////////////////////////////////////

Thu, Apr 19
SJU
ORD
8h 25m
Sun, Apr 22
ORD
SJU
6h 49m
Trip: 4 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAS
CLE
Excellent 10.0

zero problems

all great

FLL
EWR
Okay 4.6

The Crew at the desk.

My Bag is lost and yet to be found

IAH
LAS
Mediocre 3.0

Nothing to like really. Crew gathered in galley area, eating & drinking. Crew did not attend to passengers who were swinging feet & legs out in the aisle, pick up trash or other.

See above.///////////////////////////////////////////

LGA
FLL
Okay 4.6

Flight was delayed. They charged for carryon bags, they charged for water.

MCO
MSY
Mediocre 3.3

My flight being short

Paying $90 for having one piece of carry on. Not having the option to even pay for WiFi as it’s nonexistent on Spirit’s planes.

Fri, Jan 12
SJU
ORD
6h 47m
Tue, Jan 16
ORD
SJU
6h 56m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Dec 21
MBJ
ORD
4h 25m
Thu, Jan 4
ORD
MBJ
7h 21m
Trip: 15 days
6.4GoodShow reviews
Overall 6.4 Good
Based on 3 reviews
Overall
7.2
Boarding
7.3
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
MBJ
ORD
Good 6.0

Seating felt like cheap european carriers. Limited seat pockets as they try to improve legroom. Didnt let seats come back too far. so design of the cheap seating actually worked as i was not pinned in seat when jerk in frong of me put seat back.

Aisle Narrow. People at checkin were grumpy...telling us to get back ....

FAT
DEN
Excellent 8.0

Heavy Hispanic woman got ill and I was really worried she might pass away because she kept laying forward asleep or passed out on the back of the seat in front of her. Finally they found a doctor who was bilingual and he took great care of her. So bravo for that UA!

Heavy Hispanic woman got ill and I was really worried she might pass away because she kept laying forward asleep or passed out on the back of the seat in front of her. Finally they found a doctor who was bilingual and he took great care of her. So bravo for that UA!

DEN
IAD
Okay 4.3

Staff was friendly

United has a system glitch and we were delayed. I got in around 1 am instead of 11 pm. I decide to order a glass of wine and since they don’t give receipts. I found out i was charged for 2 glasses instead of one. To top it off the co-worker i was traveling with didn’t get charged due to the inconvenience and delay. i travel a lot with United (higher status than him) and would have liked that offer (and not get charged one i didn’t order) being a mileage plus and credit card holder. I did go on line and ask for a credit and they did make it right and give me a credit.

DCA
IAH
Good 7.3

Crew was great and helpful!

Not enough options for people with celiac.

MBJ
ORD
Okay 5.3

My flight was delayed by a hour and a half. They originally advised us that the delay was due to cleaning the inside of the airplane for the next passengers then they said they were fueling the plane then finally admitted there were maintenance issues with the plane. The delay cause most people to miss there connecting flights and have to stay the night since it being late evening. Inconvenience to customer

Thu, Mar 1
SJU
ORD
8h 38m
Sun, Mar 4
ORD
SJU
6h 41m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Feb 1
SJU
ORD
8h 16m
Mon, Feb 5
ORD
SJU
6h 56m
Trip: 5 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PAP
FLL
Good 7.0

My flight was very smooth, you get very pilot

I have to pay so much for my luggage. .when I get at the airport, it was my time with the spirit air lines....

LGA
FLL
Okay 4.6

Flight was delayed. They charged for carryon bags, they charged for water.

LAS
CLE
Excellent 10.0

zero problems

all great

MSY
BWI
Mediocre 2.0

Small seats

MCO
MSY
Mediocre 3.3

My flight being short

Paying $90 for having one piece of carry on. Not having the option to even pay for WiFi as it’s nonexistent on Spirit’s planes.

Tue, Feb 6
SJU
ORD
8h 16m
Tue, Feb 20
ORD
SJU
6h 51m
Trip: 15 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAS
CLE
Excellent 10.0

zero problems

all great

MCO
MSY
Mediocre 3.3

My flight being short

Paying $90 for having one piece of carry on. Not having the option to even pay for WiFi as it’s nonexistent on Spirit’s planes.

IAH
LAS
Mediocre 3.0

Nothing to like really. Crew gathered in galley area, eating & drinking. Crew did not attend to passengers who were swinging feet & legs out in the aisle, pick up trash or other.

See above.///////////////////////////////////////////

FLL
IAH
Mediocre 3.0

They moved us from the gate to have an "on-time" departure even though we sat on the taxi way for a while. Why do airlines do this? Are on time stats more important than customer comfort and satisfaction. Then they kept the lights on during the entire flight to "sell" their products. Please, give us at least a free glass of water. You are only cheaper than other airlines when you get a $9 fare, which you have to pay to have anyhow. So they are a bare bone airline, but charges are for everything. This airline stinks, I will not be flying them again unless I absolutely have to. I thought United was bad, but they are great compared to Spirit.

PAP
FLL
Good 7.0

My flight was very smooth, you get very pilot

I have to pay so much for my luggage. .when I get at the airport, it was my time with the spirit air lines....

Wed, Dec 20
MBJ
ORD
4h 25m
Wed, Jan 3
ORD
MBJ
16h 56m
Trip: 15 days
6.4GoodShow reviews
Overall 6.4 Good
Based on 3 reviews
Overall
7.2
Boarding
7.3
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
DEN
IAD
Okay 4.3

Staff was friendly

United has a system glitch and we were delayed. I got in around 1 am instead of 11 pm. I decide to order a glass of wine and since they don’t give receipts. I found out i was charged for 2 glasses instead of one. To top it off the co-worker i was traveling with didn’t get charged due to the inconvenience and delay. i travel a lot with United (higher status than him) and would have liked that offer (and not get charged one i didn’t order) being a mileage plus and credit card holder. I did go on line and ask for a credit and they did make it right and give me a credit.

MBJ
ORD
Good 6.0

Seating felt like cheap european carriers. Limited seat pockets as they try to improve legroom. Didnt let seats come back too far. so design of the cheap seating actually worked as i was not pinned in seat when jerk in frong of me put seat back.

Aisle Narrow. People at checkin were grumpy...telling us to get back ....

MBJ
ORD
Excellent 8.0

Service

Nothing

HNL
LAX
Okay 5.6

Flight was delayed over 8 hours due to "mechanical issues." Went from a nice 757 to a 737 which was a little more cramped.

SJC
EWR
Mediocre 3.6

Arrived on time

Narrow seat

Wed, Jan 10
SJU
ORD
14h 17m
Sun, Jan 14
ORD
SJU
7h 15m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Mar 1
SJU
ORD
8h 38m
Mon, Mar 5
ORD
SJU
6h 51m
Trip: 5 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
FLL
LGA
Okay 5.3

Nice professional crew.

No movies.

PAP
FLL
Good 7.0

My flight was very smooth, you get very pilot

I have to pay so much for my luggage. .when I get at the airport, it was my time with the spirit air lines....

ATL
MSY
Excellent 10.0

I've got a lot of travel bags. None are the "personal" size you demand. The bag I used, was actually overall smaller than required, though one dimension was 1 inch to wide to fit in the box. The Gate Attendant said it was no problem. My concern is what the next Attendant say? Your baggage prices are too high!

The price for the trip in the large front seats! I'm a big guy.

MCO
MSY
Mediocre 3.3

My flight being short

Paying $90 for having one piece of carry on. Not having the option to even pay for WiFi as it’s nonexistent on Spirit’s planes.

FLL
IAH
Mediocre 3.0

They moved us from the gate to have an "on-time" departure even though we sat on the taxi way for a while. Why do airlines do this? Are on time stats more important than customer comfort and satisfaction. Then they kept the lights on during the entire flight to "sell" their products. Please, give us at least a free glass of water. You are only cheaper than other airlines when you get a $9 fare, which you have to pay to have anyhow. So they are a bare bone airline, but charges are for everything. This airline stinks, I will not be flying them again unless I absolutely have to. I thought United was bad, but they are great compared to Spirit.

Sat, Dec 16
NAS
ORD
19h 02m
Tue, Jan 2
ORD
NAS
3h 20m
Trip: 18 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 4 reviews
Overall
7.2
Boarding
7.3
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
HNL
LAX
Okay 5.6

Flight was delayed over 8 hours due to "mechanical issues." Went from a nice 757 to a 737 which was a little more cramped.

SJC
EWR
Mediocre 3.6

Arrived on time

Narrow seat

NAS
ORD
Excellent 10.0

Flight down was without delay and comfortable

Flight back was delayed due to a comedy of errors with Bahama over uploading potable water.

DCA
IAH
Good 7.3

Crew was great and helpful!

Not enough options for people with celiac.

NAS
ORD
Okay 5.0

The airport employees and the flight itself were fine. We had one gentleman who came over joked with us a bit while still helping us. The flight also seemed smooth.

The boarding seemed extra slow and then we arrived at our seats and the drunk idiot who was removed from the flight causing the ridiculous delay was in them. Our friends took unused seats and we used theirs. I told him to calm down and his friends did repeatedly as well. By the time we left the airport we were 2 hours behind.

*
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