Find Cheap Flights from San Juan to Chicago (PR1 - CHI)

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Book cheap flights from San Juan to Chicago (round-trip)

Airports
Origin
San Juan
$275
only
$275
Destination
Chicago
$275
only
$275
Fri, Jan 19
SJU
ORD
19h 20m
Wed, Jan 24
ORD
SJU
22h 25m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jan 9
SJU
ORD
17h 56m
Tue, Jan 30
ORD
SJU
17h 47m
Trip: 22 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51220 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
MSY
BWI
Excellent 10.0

Everything was just perfect! Boarding and checking in didn’t take long at all which was great.

BDL
TPA
Okay 5.0

Flight not full and they still jammed people 3 to a row. Web site confusing and difficult to use, unable to get a real person on the phone for help. My cheap fare doubled at check in due to baggage charges that were not made clear in advance. No email confirmation of flight. I would not fly Spirit again despite the fare,

MCO
SJU
Excellent 10.0

Carry on bag fee

ATL
MSP
Excellent 10.0

First time flying loved it

I didn't know what to expect

LAX
OAK
Excellent 10.0

Everything went smoothly.

Tue, Feb 6
SJU
ORD
6h 47m
Tue, Feb 20
ORD
SJU
6h 47m
Trip: 15 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 4 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
FLL
KIN
Okay 4.0

The flight attendants were pleasant and courteous

The boarding was delayed and the boarding area was crowded, Boarding was delayed due to high number of wheelchair passengers. I was seated in an Even More Space seat, yet was placed beside a woman who was obviously suffering from some degenerative condition, and was slumped over towards my seat. The result was that I was uncomfortable the whole way back to Kingston.

SEA
JFK
Excellent 8.0

no power outlets

PHX
JFK
Good 7.6

The staff is friendlier than most airlines. More room than American.

Screaming child entire flight. Not sure there is a solution. But, for a redeye, trying to get sleep before a days work, not great.

JFK
ABQ
Good 7.3

I know it's hard to make a 14+ hour flight in economy enjoyable, but more varied food selections and better/more current movies to choose from would have helped.

BOS
PBI
Excellent 8.3

my attendant

Wed, Feb 7
SJU
ORD
8h 14m
Wed, Feb 14
ORD
SJU
22h 25m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Feb 7
SJU
ORD
8h 14m
Tue, Feb 13
ORD
SJU
6h 57m
Trip: 7 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51220 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
BDL
TPA
Okay 5.0

Flight not full and they still jammed people 3 to a row. Web site confusing and difficult to use, unable to get a real person on the phone for help. My cheap fare doubled at check in due to baggage charges that were not made clear in advance. No email confirmation of flight. I would not fly Spirit again despite the fare,

PHX
ORD
Mediocre 3.6

Boarded the aircraft quickly and left on time.

Airplane reeked of vomit and vinegar. Seats were dirty and you have to pay for water.

MCO
SJU
Excellent 10.0

Carry on bag fee

ATL
MSP
Excellent 10.0

First time flying loved it

I didn't know what to expect

CLE
LAX
Excellent 8.6

It was on time, easy to board and I got extra leg room at no additional charge.

Wish you offered on flight movie.

Wed, Feb 7
SJU
ORD
6h 47m
Mon, Feb 12
ORD
SJU
6h 46m
Trip: 6 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 4 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
FLL
RDU
Excellent 8.3

The departure and arrival times were accurate. Actually we arrived about 15 minutes early.

There was only one individual checking people boarding. Two individuals at the boarding gate would have been even more efficient.

PHX
JFK
Good 7.6

The staff is friendlier than most airlines. More room than American.

Screaming child entire flight. Not sure there is a solution. But, for a redeye, trying to get sleep before a days work, not great.

BOS
PBI
Excellent 8.3

my attendant

SFO
FLL
Good 7.0

Once again the system for my seat did not work. Fortunately, the middle seat was empty and I wa able to watch that screen.

Entertainment System did not work at my seat. WiFi signal was not strong enough for me to watch any videos on my device.

MCO
DCA
Excellent 10.0

Left on time and arrived early both ways.

Mon, Jan 15
SJU
ORD
19h 20m
Mon, Jan 22
ORD
SJU
22h 25m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jan 23
SJU
ORD
8h 14m
Tue, Feb 6
ORD
SJU
6h 57m
Trip: 15 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51220 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
CLE
LAX
Excellent 8.6

It was on time, easy to board and I got extra leg room at no additional charge.

Wish you offered on flight movie.

ORD
LGA
Good 6.3

Flight and gate staff were great

Waited 45 minutes in line to check our bag. Ours was the third or fourth flight of the day. How were the check in staff so far behind so early??

ATL
FLL
Excellent 10.0

Dwight the flight attendant was amazing made the flight the best.

Having to pay 55 for a bag.

BDL
TPA
Okay 5.0

Flight not full and they still jammed people 3 to a row. Web site confusing and difficult to use, unable to get a real person on the phone for help. My cheap fare doubled at check in due to baggage charges that were not made clear in advance. No email confirmation of flight. I would not fly Spirit again despite the fare,

ATL
MSP
Excellent 10.0

First time flying loved it

I didn't know what to expect

Wed, Feb 14
SJU
ORD
6h 47m
Wed, Feb 21
ORD
SJU
6h 47m
Trip: 8 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 4 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
MCO
DCA
Excellent 10.0

Left on time and arrived early both ways.

BOS
DCA
Mediocre 2.0

There was a huge glitch in your ticketing, resulting in me confirming the same ticket 3 times. After calling Jetblue for customer service per your advice, they first suggested to give Jetblue credits for extra tickets. When I insisted that the issue was solely caused by kayak-jetblue ticketing connection issues, they supervisor approved to cancel 2 credit card payments... BUT I have to wait for 2 weeks to see the cancellation on my credit card. Unfair and ridiculous, if you as me.

SFO
FLL
Good 7.0

Once again the system for my seat did not work. Fortunately, the middle seat was empty and I wa able to watch that screen.

Entertainment System did not work at my seat. WiFi signal was not strong enough for me to watch any videos on my device.

PHX
JFK
Good 7.6

The staff is friendlier than most airlines. More room than American.

Screaming child entire flight. Not sure there is a solution. But, for a redeye, trying to get sleep before a days work, not great.

FLL
LAS
Good 6.3

The flight was delayed by 2 hours

Tue, Jan 23
SJU
ORD
8h 14m
Mon, Jan 29
ORD
SJU
22h 25m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Feb 6
SJU
ORD
8h 14m
Wed, Feb 14
ORD
SJU
6h 57m
Trip: 9 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51220 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
TPA
ORD
Mediocre 2.0

The plane was very dated. The seats were broken (did not recline). Did arrive on time which was a plus.

Overall Bad Experience

LAX
OAK
Excellent 10.0

Everything went smoothly.

SAN
LAS
Excellent 9.0

Friendly staff

Would like option to add carry on during ticket purchase. Did not see this when I booked so had to pay extra upon arrival. If it’s there is easily missed.

ORD
LGA
Good 6.3

Flight and gate staff were great

Waited 45 minutes in line to check our bag. Ours was the third or fourth flight of the day. How were the check in staff so far behind so early??

ATL
FLL
Excellent 10.0

Dwight the flight attendant was amazing made the flight the best.

Having to pay 55 for a bag.

Thu, Feb 22
SJU
ORD
6h 47m
Tue, Feb 27
ORD
SJU
6h 41m
Trip: 6 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 4 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
FLL
RDU
Excellent 8.3

The departure and arrival times were accurate. Actually we arrived about 15 minutes early.

There was only one individual checking people boarding. Two individuals at the boarding gate would have been even more efficient.

MCO
DCA
Excellent 10.0

Left on time and arrived early both ways.

PHX
JFK
Good 7.6

The staff is friendlier than most airlines. More room than American.

Screaming child entire flight. Not sure there is a solution. But, for a redeye, trying to get sleep before a days work, not great.

MCO
PVD
Excellent 10.0

Great flight great experience

Long lines at TSA checkpoint.

JFK
SYR
Good 7.0

TV didn't work

Sat, Jan 27
SJU
ORD
8h 14m
Mon, Feb 5
ORD
SJU
22h 25m
Trip: 10 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Feb 8
SJU
ORD
8h 14m
Wed, Feb 14
ORD
SJU
6h 57m
Trip: 7 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51220 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
CLE
LAX
Excellent 8.6

It was on time, easy to board and I got extra leg room at no additional charge.

Wish you offered on flight movie.

LAX
OAK
Excellent 10.0

Everything went smoothly.

ORD
LGA
Good 6.3

Flight and gate staff were great

Waited 45 minutes in line to check our bag. Ours was the third or fourth flight of the day. How were the check in staff so far behind so early??

PHX
ORD
Mediocre 3.6

Boarded the aircraft quickly and left on time.

Airplane reeked of vomit and vinegar. Seats were dirty and you have to pay for water.

ATL
MSP
Excellent 10.0

First time flying loved it

I didn't know what to expect

Tue, Jan 16
SJU
ORD
9h 54m
Tue, Jan 23
ORD
SJU
6h 46m
Trip: 8 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 4 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
FLL
LAS
Good 6.3

The flight was delayed by 2 hours

MCO
PVD
Excellent 10.0

Great flight great experience

Long lines at TSA checkpoint.

SEA
JFK
Excellent 8.0

no power outlets

FLL
KIN
Okay 4.0

The flight attendants were pleasant and courteous

The boarding was delayed and the boarding area was crowded, Boarding was delayed due to high number of wheelchair passengers. I was seated in an Even More Space seat, yet was placed beside a woman who was obviously suffering from some degenerative condition, and was slumped over towards my seat. The result was that I was uncomfortable the whole way back to Kingston.

MCO
DCA
Excellent 10.0

Left on time and arrived early both ways.

Mon, Jan 22
SJU
ORD
19h 20m
Mon, Jan 29
ORD
SJU
22h 25m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Feb 14
SJU
ORD
8h 14m
Wed, Feb 28
ORD
SJU
6h 56m
Trip: 15 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51220 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
MCO
SJU
Excellent 10.0

Carry on bag fee

MSY
BWI
Excellent 10.0

Everything was just perfect! Boarding and checking in didn’t take long at all which was great.

ORD
LGA
Good 6.3

Flight and gate staff were great

Waited 45 minutes in line to check our bag. Ours was the third or fourth flight of the day. How were the check in staff so far behind so early??

RSW
DTW
Excellent 8.0

The flight was delayed for a "maintenance issue," but that's fine by me - I'm glad they are checking planes thoroughly before take-off. They got us out of the gate faster than predicted, and everything went fine from there.

The flight was delayed for a "maintenance issue," but that's fine by me - I'm glad they are checking planes thoroughly before take-off. They got us out of the gate faster than predicted, and everything went fine from there.

ATL
MSP
Excellent 10.0

First time flying loved it

I didn't know what to expect

Tue, Jan 30
SJU
ORD
9h 54m
Tue, Feb 6
ORD
SJU
6h 46m
Trip: 8 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 4 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
SFO
FLL
Good 7.0

Once again the system for my seat did not work. Fortunately, the middle seat was empty and I wa able to watch that screen.

Entertainment System did not work at my seat. WiFi signal was not strong enough for me to watch any videos on my device.

MCO
DCA
Excellent 10.0

Left on time and arrived early both ways.

FLL
LAS
Good 6.3

The flight was delayed by 2 hours

JFK
ABQ
Good 7.3

I know it's hard to make a 14+ hour flight in economy enjoyable, but more varied food selections and better/more current movies to choose from would have helped.

BOS
PBI
Excellent 8.3

my attendant

Tue, Jan 9
SJU
ORD
17h 56m
Tue, Jan 16
ORD
SJU
6h 57m
Trip: 8 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51220 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
LGA
Good 6.3

Flight and gate staff were great

Waited 45 minutes in line to check our bag. Ours was the third or fourth flight of the day. How were the check in staff so far behind so early??

MCO
SJU
Excellent 10.0

Carry on bag fee

MSY
BWI
Excellent 10.0

Everything was just perfect! Boarding and checking in didn’t take long at all which was great.

ATL
FLL
Excellent 10.0

Dwight the flight attendant was amazing made the flight the best.

Having to pay 55 for a bag.

RSW
DTW
Excellent 8.0

The flight was delayed for a "maintenance issue," but that's fine by me - I'm glad they are checking planes thoroughly before take-off. They got us out of the gate faster than predicted, and everything went fine from there.

The flight was delayed for a "maintenance issue," but that's fine by me - I'm glad they are checking planes thoroughly before take-off. They got us out of the gate faster than predicted, and everything went fine from there.

Mon, Jan 29
SJU
ORD
19h 20m
Mon, Feb 5
ORD
SJU
22h 25m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
*
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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.