Find Cheap Flights from Jamaica to Chicago

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Fri 12/15
Fri 12/22
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Book cheap flights from Jamaica to Chicago (round-trip)

Airports
Origin
Montego Bay
$375
only
$375
Kingston
$465
only
$465
Destination
Chicago
$375
only
$375
$563
only
$563
Wed, Dec 27
MBJ
ORD
4h 25m
Wed, Jan 3
ORD
MBJ
17h 44m
Trip: 8 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 4 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
RSW
EWR
Okay 5.3

Waiting

MBJ
ORD
Excellent 8.6

Made up all delays in the air

RSW
EWR
Okay 5.3

Boarding quickly

No PED was available didn’t have anything for entertainment if you weren’t buying it seems every thing available for 3 hour flight and flight was scheduled for 2 hours and 55 minutes No snacks made available came thru once had a small bag of pretzels cup of coffee and never came back

MBJ
ORD
Excellent 8.0

Service

Nothing

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 ....

Wed, Dec 20
MBJ
ORD
9h 43m
Tue, Jan 9
ORD
MBJ
9h 02m
Trip: 21 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Dec 22
MBJ
ORD
8h 33m
Tue, Jan 9
ORD
MBJ
9h 02m
Trip: 19 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51195 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAX
CLE
Excellent 10.0

Nice crew, clean planes, problem free

I chose my isle seat on line... paid for it ... however assigned a middle seat when I boarded. I have medical issues so I always request an asle seat. So this was very disheartening. I should at least be reimbursed for my seat selection fee. Note: I do not complain on any Airline for fear of what happened to United passenger and being African American.

IAH
DEN
Mediocre 3.3

Flight good very basic plane like they don’t even have a pocket holder and the tray is minuscule. The chairs are pretty firm but not bad for my 2 hour flight.

My baggage was damaged , found open with one of the contents upon top of luggage, found it after beltmstopped and couldn’t find mine, I asked about it and Spirit lady said it’s to the side

ORD
LAS
Okay 5.3

The friendliness of the crew

Very hot and uncomfortable

LAX
FLL
Mediocre 2.0

No entertainment, no food, no even water, the flight was delayed 3 hours st the last minute and close to the time it was changed for a 2.5 your delay. Complete desorganized. And they change 60 dollars For the check in baggage and 50 for the carry on. Nothing included. It’s my first and last time flying with Spirit

LAS
DFW
Excellent 8.0

Seats do not recline even in big seats

Thu, Jan 11
KIN
ORD
14h 01m
Wed, Jan 17
ORD
KIN
15h 14m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26019 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
ABQ
ORD
Excellent 8.0

everything fine

having to gate-check our hand luggage

LAX
NRT
Mediocre 2.0

nothing

had to take another flight, ticket agent was able to change me to a different flight on JAL. however, JAL could not access the ticket info and ticket agent would not take my payment. result was missing that flight, ticket manager told me it's my fault and tough luck no refund. American airlines told me the same, ended up losing my money for the ticket purchase. i booked another new flight with another airline direct. worst experience in my life using kayak.

AUS
CLT
Excellent 10.0

My Mom was very grateful for the friendly assistance as she is wheelchair bound and was flying aline. Excellent service!!

Nothing.

BOS
JFK
Good 6.0

No hassle of changing terminals in JFK, no bagagge claim, AA check-in-this time, was a "good luck"....Connection in Helsinki, very quik!

Finnair flight AY06 are old aircrafts. Every other in-seat monitor was out of order, flight attendants could not do much. That created mess for passengers, trying to move their seats to the ones with working monitors.....

TPA
ORD
Excellent 8.0

Average. Expectation for US airlines are so low this flight score average.

Wed, Jun 20
KIN
ORD
7h 38m
Fri, Jun 29
ORD
KIN
11h 01m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
GSO
ATL
Excellent 10.0

Plane nice and comfortable

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

Thu, Dec 21
MBJ
ORD
4h 25m
Thu, Jan 4
ORD
MBJ
16h 56m
Trip: 15 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 4 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
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

MBJ
ORD
Excellent 8.0

Service

Nothing

ORD
LAS
Okay 4.0

The crew was helpful and friendly, my flight was inexpensive

The seats were incredibly uncomfortable! Also, many people did not understand how to turn off the televisions, so it was pretty distracting to have so many monitors going when we all trying to sleep.

RSW
EWR
Okay 5.3

Waiting

MBJ
ORD
Excellent 8.6

Made up all delays in the air

Wed, Dec 27
MBJ
ORD
8h 33m
Wed, Jan 3
ORD
MBJ
9h 02m
Trip: 8 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51195 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ATL
DFW
Mediocre 2.0

Spirit was completely horrible , customer service was completely horrible!

DEN
FLL
Okay 4.3

Price, schedule

Very uncomfortable seats, seats do not recline, very cramped seating

ORD
LAS
Okay 5.3

The friendliness of the crew

Very hot and uncomfortable

LAS
MSY
Okay 5.3

Crew

$55 per carry-on. For 4 People the bags will almost double the cost of the ticket.

SAN
LAS
Mediocre 2.0

Nothing, at first how cheap it was, but one quickly realizes you get what they paid for.

The fact that they blamed the weather for their in ability to land, but the reality is that the airline is so cheap they don't carry enough fuel to be able to give it another go at landing in Las Vegas. We were literally only about 15 20 feet from landing at our destination when the pilot decided to speed up and give it another go. But then they gave us some b.s. about how their gate was taken and they had no other available gates, but then they blamed the weather. Wish they could get their story straight. Anyway, the airline just stranded us in Los Angeles, which is even weirder since we took off from San Diego...

Fri, Jan 12
KIN
ORD
16h 57m
Thu, Jan 18
ORD
KIN
6h 29m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26019 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LAX
NRT
Mediocre 2.0

nothing

had to take another flight, ticket agent was able to change me to a different flight on JAL. however, JAL could not access the ticket info and ticket agent would not take my payment. result was missing that flight, ticket manager told me it's my fault and tough luck no refund. American airlines told me the same, ended up losing my money for the ticket purchase. i booked another new flight with another airline direct. worst experience in my life using kayak.

BOS
JFK
Good 6.0

No hassle of changing terminals in JFK, no bagagge claim, AA check-in-this time, was a "good luck"....Connection in Helsinki, very quik!

Finnair flight AY06 are old aircrafts. Every other in-seat monitor was out of order, flight attendants could not do much. That created mess for passengers, trying to move their seats to the ones with working monitors.....

TPA
ORD
Excellent 8.0

Average. Expectation for US airlines are so low this flight score average.

ABQ
ORD
Excellent 8.0

everything fine

having to gate-check our hand luggage

HPN
DCA
Mediocre 2.0

Nothing

Comfort, timeliness.

Wed, Dec 20
MBJ
ORD
4h 25m
Wed, Jan 3
ORD
MBJ
18h 15m
Trip: 15 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 4 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
LAX
YVR
Excellent 8.0

Checking in was simple with no problems. They made the process easy. Very courteous!

MIA
ORD
Excellent 9.0

That it got me to Paris safe

No outlets to charge your phone, and the tv played the same movie over and over. The meals were also cheap. Didn't like any of them. Should have flown southwest or delta.

MBJ
ORD
Excellent 8.6

Made up all delays in the air

LAX
EWR
Good 7.6

I had the row to myself. Smooth flight. On time. Actually we got there early.

My arm rest would not stay up. Flight attendant almost seemed rude. Might have been just her tone. She seemed annoyed. I could be wrong.

PUJ
EWR
Good 7.3

The flight was very hot and uncomfortable

Thu, Dec 21
MBJ
ORD
8h 33m
Thu, Jan 4
ORD
MBJ
19h 58m
Trip: 15 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51195 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAS
DFW
Excellent 8.0

Seats do not recline even in big seats

ORD
LAS
Okay 5.3

The friendliness of the crew

Very hot and uncomfortable

DEN
FLL
Okay 4.3

Price, schedule

Very uncomfortable seats, seats do not recline, very cramped seating

SAN
LAS
Mediocre 2.0

Nothing, at first how cheap it was, but one quickly realizes you get what they paid for.

The fact that they blamed the weather for their in ability to land, but the reality is that the airline is so cheap they don't carry enough fuel to be able to give it another go at landing in Las Vegas. We were literally only about 15 20 feet from landing at our destination when the pilot decided to speed up and give it another go. But then they gave us some b.s. about how their gate was taken and they had no other available gates, but then they blamed the weather. Wish they could get their story straight. Anyway, the airline just stranded us in Los Angeles, which is even weirder since we took off from San Diego...

EWR
LAS
Excellent 8.0

Over all I had nice experience

Thu, Jun 21
KIN
ORD
7h 38m
Fri, Jun 29
ORD
KIN
11h 01m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

LGA
YUL
Excellent 8.0

it was easy to navigate .

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

SEA
LAX
Okay 4.0

Nothing, they didn’t care about you or to help, the llady was so rude and unfriendly, this situation ruin my whole trip

I call in advance to paid the fees for baggage, I call Aeromexico because was the main airline for the fly, but Delta at Seattle made me paid again the fees for baggage’s even by phone they said that I didn’t need to paid. BE AWARE AND CAREFUL BECAUSE THE LADIES IN THE FRONT DESK didn’t even look the paperwork that you have in hand, they only want to charge you saying that your payment thru Aeromexico didn’t help you in the 1st fly. How this can happen when Delta and Aeromexico are two subsidiary one of another ?

Fri, Jan 12
KIN
ORD
18h 38m
Thu, Jan 18
ORD
KIN
7h 55m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Dec 27
MBJ
MDW
7h 29m
Wed, Jan 3
MDW
MBJ
7h 50m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

SEA
LAX
Okay 4.0

Nothing, they didn’t care about you or to help, the llady was so rude and unfriendly, this situation ruin my whole trip

I call in advance to paid the fees for baggage, I call Aeromexico because was the main airline for the fly, but Delta at Seattle made me paid again the fees for baggage’s even by phone they said that I didn’t need to paid. BE AWARE AND CAREFUL BECAUSE THE LADIES IN THE FRONT DESK didn’t even look the paperwork that you have in hand, they only want to charge you saying that your payment thru Aeromexico didn’t help you in the 1st fly. How this can happen when Delta and Aeromexico are two subsidiary one of another ?

GSO
ATL
Excellent 10.0

Plane nice and comfortable

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

Fri, Jan 12
KIN
ORD
18h 38m
Wed, Jan 17
ORD
KIN
10h 24m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Dec 21
KIN
ORD
9h 53m
Sun, Dec 24
ORD
KIN
18h 55m
Trip: 4 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51195 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
DEN
FLL
Okay 4.3

Price, schedule

Very uncomfortable seats, seats do not recline, very cramped seating

EWR
LAS
Excellent 8.0

Over all I had nice experience

IAH
DEN
Mediocre 3.3

Flight good very basic plane like they don’t even have a pocket holder and the tray is minuscule. The chairs are pretty firm but not bad for my 2 hour flight.

My baggage was damaged , found open with one of the contents upon top of luggage, found it after beltmstopped and couldn’t find mine, I asked about it and Spirit lady said it’s to the side

LGA
DTW
Mediocre 3.0

Seats are clean. Cabin looks new.

Seats are very narrow. Anyone slightly overweight will be spilling over into someone else's seat. The design was not made with the average person's comfort in mind.

LAX
CLE
Excellent 10.0

Nice crew, clean planes, problem free

I chose my isle seat on line... paid for it ... however assigned a middle seat when I boarded. I have medical issues so I always request an asle seat. So this was very disheartening. I should at least be reimbursed for my seat selection fee. Note: I do not complain on any Airline for fear of what happened to United passenger and being African American.

Thu, Dec 28
KIN
ORD
8h 07m
Mon, Jan 1
ORD
KIN
7h 59m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jun 20
MBJ
ORD
8h 56m
Fri, Jun 29
ORD
MBJ
15h 05m
Trip: 10 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51195 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAX
CLE
Excellent 10.0

Nice crew, clean planes, problem free

I chose my isle seat on line... paid for it ... however assigned a middle seat when I boarded. I have medical issues so I always request an asle seat. So this was very disheartening. I should at least be reimbursed for my seat selection fee. Note: I do not complain on any Airline for fear of what happened to United passenger and being African American.

ATL
DFW
Mediocre 2.0

Spirit was completely horrible , customer service was completely horrible!

SAN
LAS
Mediocre 2.0

Nothing, at first how cheap it was, but one quickly realizes you get what they paid for.

The fact that they blamed the weather for their in ability to land, but the reality is that the airline is so cheap they don't carry enough fuel to be able to give it another go at landing in Las Vegas. We were literally only about 15 20 feet from landing at our destination when the pilot decided to speed up and give it another go. But then they gave us some b.s. about how their gate was taken and they had no other available gates, but then they blamed the weather. Wish they could get their story straight. Anyway, the airline just stranded us in Los Angeles, which is even weirder since we took off from San Diego...

DEN
FLL
Okay 4.3

Price, schedule

Very uncomfortable seats, seats do not recline, very cramped seating

EWR
LAS
Excellent 8.0

Over all I had nice experience

Thu, Jan 11
KIN
MDW
7h 20m
Wed, Jan 17
MDW
KIN
8h 23m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

SEA
LAX
Okay 4.0

Nothing, they didn’t care about you or to help, the llady was so rude and unfriendly, this situation ruin my whole trip

I call in advance to paid the fees for baggage, I call Aeromexico because was the main airline for the fly, but Delta at Seattle made me paid again the fees for baggage’s even by phone they said that I didn’t need to paid. BE AWARE AND CAREFUL BECAUSE THE LADIES IN THE FRONT DESK didn’t even look the paperwork that you have in hand, they only want to charge you saying that your payment thru Aeromexico didn’t help you in the 1st fly. How this can happen when Delta and Aeromexico are two subsidiary one of another ?

Thu, Jun 21
MBJ
ORD
9h 06m
Fri, Jun 29
ORD
MBJ
15h 05m
Trip: 9 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51195 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
DEN
FLL
Okay 4.3

Price, schedule

Very uncomfortable seats, seats do not recline, very cramped seating

LAS
DFW
Excellent 8.0

Seats do not recline even in big seats

IAH
DEN
Mediocre 3.3

Flight good very basic plane like they don’t even have a pocket holder and the tray is minuscule. The chairs are pretty firm but not bad for my 2 hour flight.

My baggage was damaged , found open with one of the contents upon top of luggage, found it after beltmstopped and couldn’t find mine, I asked about it and Spirit lady said it’s to the side

ATL
DFW
Mediocre 2.0

Spirit was completely horrible , customer service was completely horrible!

LAX
FLL
Mediocre 2.0

No entertainment, no food, no even water, the flight was delayed 3 hours st the last minute and close to the time it was changed for a 2.5 your delay. Complete desorganized. And they change 60 dollars For the check in baggage and 50 for the carry on. Nothing included. It’s my first and last time flying with Spirit

Fri, Dec 22
KIN
MDW
7h 24m
Wed, Jan 3
MDW
KIN
6h 45m
$1106
Trip: 13 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
LAX
Okay 4.0

Nothing, they didn’t care about you or to help, the llady was so rude and unfriendly, this situation ruin my whole trip

I call in advance to paid the fees for baggage, I call Aeromexico because was the main airline for the fly, but Delta at Seattle made me paid again the fees for baggage’s even by phone they said that I didn’t need to paid. BE AWARE AND CAREFUL BECAUSE THE LADIES IN THE FRONT DESK didn’t even look the paperwork that you have in hand, they only want to charge you saying that your payment thru Aeromexico didn’t help you in the 1st fly. How this can happen when Delta and Aeromexico are two subsidiary one of another ?

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

*
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