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

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

Airports
Origin
Chicago
$270
only
$270
Destination
San Juan
$270
only
$270
Wed, Jan 17
ORD
SJU
6h 57m
Tue, Jan 23
SJU
ORD
24h 55m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jan 17
ORD
SJU
6h 57m
Wed, Jan 24
SJU
ORD
8h 14m
Trip: 8 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51176 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

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

FLL
EWR
Mediocre 3.6

Flight was smooth, planes are new and the flight crew was nice.

There’s a charge for everything under the sun. And the baggage weight limit is 40 vs the industry standard of 50. Airport personnel were lazy.

DEN
FLL
Okay 4.3

Price, schedule

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

ORD
BWI
Mediocre 2.0

I had to cancel my flight because I did not want to miss my daughters baptism. I did not know the date of her baptism when I booked the flight. When I I tried to change the flight it would have cost twice as much. I’ve always loved flying with Spirit. Until this time. When I asked if I could get a travel voucher for a future date I was told it was a promotion so I could only get a $10 credit even though the price I paid was $120. I’m so sad.

Tue, Feb 20
ORD
SJU
6h 47m
Wed, Feb 28
SJU
ORD
8h 00m
Trip: 9 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 1 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
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
SYR
Good 7.0

TV didn't work

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.

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.

Sat, Jan 20
ORD
SJU
6h 57m
Tue, Jan 23
SJU
ORD
24h 55m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jan 20
ORD
SJU
6h 57m
Wed, Jan 24
SJU
ORD
8h 14m
Trip: 5 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51176 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

TPA
CLE
Excellent 10.0

Price an service

The same price today

MSY
BWI
Excellent 10.0

Flight was on time and arrived at destination 20 minutes earlier.

Nothing

LAS
DFW
Excellent 8.0

Seats do not recline even in big seats

ORD
BWI
Mediocre 2.0

I had to cancel my flight because I did not want to miss my daughters baptism. I did not know the date of her baptism when I booked the flight. When I I tried to change the flight it would have cost twice as much. I’ve always loved flying with Spirit. Until this time. When I asked if I could get a travel voucher for a future date I was told it was a promotion so I could only get a $10 credit even though the price I paid was $120. I’m so sad.

Wed, Feb 21
ORD
SJU
6h 47m
Wed, Feb 28
SJU
ORD
8h 00m
Trip: 8 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 1 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
JFK
SYR
Good 7.0

TV didn't work

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.

ORD
SJU
Good 7.6

Great flight with roomy seats, wifi and goodies

Horrible terminal 3 at O'Hare has one body scanner--one!--for all flights departing. Huge wait at security. I bought the JetBlue Even More Speed for $10 on their mobile app which is an option that can be done after you check in. It charges your credit card and does not update your boarding pass. TSA would not allow us in speed line, had to go back to jetblue desk and get paper passes---JetBlue counter agents so harsh about it they made me cry. Awful omni channel experience.

MCO
DCA
Excellent 10.0

Left on time and arrived early both ways.

FLL
LGA
Good 7.6

Onboarding crew was a bit rude and rushing everyone. Forcing people to check in bags even though there was still space in the overhead bins.

Mon, Jan 15
ORD
SJU
22h 25m
Tue, Jan 23
SJU
ORD
24h 55m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jan 30
ORD
SJU
17h 47m
Wed, Feb 7
SJU
ORD
8h 14m
Trip: 9 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51176 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAS
DEN
Good 6.0

The quickness of boarding etc.

You really don't save any money at all after paying for a checked bag and then seats if you want to sit next to your loved one. Plus the leg room/spaciousness is to be desired!

ORD
BWI
Mediocre 2.0

I had to cancel my flight because I did not want to miss my daughters baptism. I did not know the date of her baptism when I booked the flight. When I I tried to change the flight it would have cost twice as much. I’ve always loved flying with Spirit. Until this time. When I asked if I could get a travel voucher for a future date I was told it was a promotion so I could only get a $10 credit even though the price I paid was $120. I’m so sad.

TPA
CLE
Excellent 10.0

Price an service

The same price today

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...

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

Wed, Feb 21
ORD
SJU
6h 47m
Wed, Feb 28
SJU
ORD
8h 00m
Trip: 8 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 1 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.

FLL
LGA
Good 7.6

Onboarding crew was a bit rude and rushing everyone. Forcing people to check in bags even though there was still space in the overhead bins.

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.

ORD
SJU
Good 7.6

Great flight with roomy seats, wifi and goodies

Horrible terminal 3 at O'Hare has one body scanner--one!--for all flights departing. Huge wait at security. I bought the JetBlue Even More Speed for $10 on their mobile app which is an option that can be done after you check in. It charges your credit card and does not update your boarding pass. TSA would not allow us in speed line, had to go back to jetblue desk and get paper passes---JetBlue counter agents so harsh about it they made me cry. Awful omni channel experience.

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.

Thu, Jan 18
ORD
SJU
6h 57m
Tue, Jan 23
SJU
ORD
24h 55m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jan 16
ORD
SJU
6h 57m
Tue, Jan 30
SJU
ORD
8h 14m
Trip: 15 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51176 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
EWR
LAS
Excellent 8.0

Over all I had nice experience

DEN
FLL
Okay 4.3

Price, schedule

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

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

ORD
BWI
Mediocre 2.0

I had to cancel my flight because I did not want to miss my daughters baptism. I did not know the date of her baptism when I booked the flight. When I I tried to change the flight it would have cost twice as much. I’ve always loved flying with Spirit. Until this time. When I asked if I could get a travel voucher for a future date I was told it was a promotion so I could only get a $10 credit even though the price I paid was $120. I’m so sad.

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.

Tue, Feb 27
ORD
SJU
6h 41m
Tue, Mar 6
SJU
ORD
8h 00m
Trip: 8 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 1 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
ORD
SJU
Good 7.6

Great flight with roomy seats, wifi and goodies

Horrible terminal 3 at O'Hare has one body scanner--one!--for all flights departing. Huge wait at security. I bought the JetBlue Even More Speed for $10 on their mobile app which is an option that can be done after you check in. It charges your credit card and does not update your boarding pass. TSA would not allow us in speed line, had to go back to jetblue desk and get paper passes---JetBlue counter agents so harsh about it they made me cry. Awful omni channel experience.

SEA
JFK
Excellent 8.0

no power outlets

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.

JFK
SYR
Good 7.0

TV didn't work

JFK
ROC
Mediocre 2.3

Our prior flight arrived 30 minutes late and we had to run to the opposite side of the airport. We were there before the departure time but the staff gave us a hard time saying they were going to lock the doors on us. It wasn't until the flight crew ran up behind us that they finally didn't have an attitude and said we were fine. Online entertainment didn't work, no shows, the map doesn't have a time or useful info. My row was skipped by the crew for snacks. The guy came from behind first, which I didn't see and then one the way back, he didn't even look at my row or the row in front of me.

Mon, Feb 5
ORD
SJU
22h 25m
Wed, Feb 14
SJU
ORD
8h 14m
Trip: 10 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jan 17
ORD
SJU
6h 57m
Sat, Jan 27
SJU
ORD
8h 14m
Trip: 11 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51176 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
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

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

LAS
DFW
Excellent 8.0

Seats do not recline even in big seats

FLL
EWR
Mediocre 3.6

Flight was smooth, planes are new and the flight crew was nice.

There’s a charge for everything under the sun. And the baggage weight limit is 40 vs the industry standard of 50. Airport personnel were lazy.

Tue, Feb 27
ORD
SJU
6h 41m
Tue, Mar 6
SJU
ORD
8h 00m
Trip: 8 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 1 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
FLL
LGA
Good 7.6

Onboarding crew was a bit rude and rushing everyone. Forcing people to check in bags even though there was still space in the overhead bins.

LAX
MCO
Excellent 8.0

Jet Blue didn’t transfer my baggage to the company which I would fly with after, and if the office didn’t call me I would have my luggage lost. Not to mention that I had to stay caring it around the airport for 13 hours, until the time of my next flight.

ORD
SJU
Good 7.6

Great flight with roomy seats, wifi and goodies

Horrible terminal 3 at O'Hare has one body scanner--one!--for all flights departing. Huge wait at security. I bought the JetBlue Even More Speed for $10 on their mobile app which is an option that can be done after you check in. It charges your credit card and does not update your boarding pass. TSA would not allow us in speed line, had to go back to jetblue desk and get paper passes---JetBlue counter agents so harsh about it they made me cry. Awful omni channel experience.

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.

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.

Mon, Jan 15
ORD
SJU
22h 25m
Thu, Jan 25
SJU
ORD
24h 55m
Trip: 11 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jan 20
ORD
SJU
6h 57m
Sat, Jan 27
SJU
ORD
8h 14m
Trip: 8 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51176 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
FLL
EWR
Mediocre 3.6

Flight was smooth, planes are new and the flight crew was nice.

There’s a charge for everything under the sun. And the baggage weight limit is 40 vs the industry standard of 50. Airport personnel were lazy.

LAS
DEN
Good 6.0

The quickness of boarding etc.

You really don't save any money at all after paying for a checked bag and then seats if you want to sit next to your loved one. Plus the leg room/spaciousness is to be desired!

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

TPA
CLE
Excellent 10.0

Price an service

The same price today

MSY
BWI
Excellent 10.0

Flight was on time and arrived at destination 20 minutes earlier.

Nothing

Wed, Feb 28
ORD
SJU
6h 41m
Tue, Mar 6
SJU
ORD
8h 00m
Trip: 7 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 1 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
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
ROC
Mediocre 2.3

Our prior flight arrived 30 minutes late and we had to run to the opposite side of the airport. We were there before the departure time but the staff gave us a hard time saying they were going to lock the doors on us. It wasn't until the flight crew ran up behind us that they finally didn't have an attitude and said we were fine. Online entertainment didn't work, no shows, the map doesn't have a time or useful info. My row was skipped by the crew for snacks. The guy came from behind first, which I didn't see and then one the way back, he didn't even look at my row or the row in front of me.

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.

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.

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.

Sat, Jan 20
ORD
SJU
17h 47m
Thu, Jan 25
SJU
ORD
24h 55m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jan 31
ORD
SJU
6h 57m
Wed, Feb 7
SJU
ORD
8h 14m
Trip: 8 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51176 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
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...

ORD
BWI
Mediocre 2.0

I had to cancel my flight because I did not want to miss my daughters baptism. I did not know the date of her baptism when I booked the flight. When I I tried to change the flight it would have cost twice as much. I’ve always loved flying with Spirit. Until this time. When I asked if I could get a travel voucher for a future date I was told it was a promotion so I could only get a $10 credit even though the price I paid was $120. I’m so sad.

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

DEN
FLL
Okay 4.3

Price, schedule

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

*
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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.