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

Airports
Origin
Chicago
$189
only
$189
$362
only
$362
Destination
San Juan
$189
only
$189
Tue, Apr 10
ORD
SJU
7h 31m
Mon, Apr 16
SJU
ORD
8h 38m
Trip: 7 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33843 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
IAD
SAT
Mediocre 3.6

The crew was helpful and apologetic.

They purposefully understaffed the check in counter, which you have to use. They charge for every little thing, even carry on bags and snacks. The seats might as well be lawn chairs. They are so close together everyone onboard will die from head injuries if there's an accident. I'll fly Southwest from now on.

ISP
MIA
Excellent 10.0

Great flight from Islip to MIA. Looked at another review about water on flights and I was told by the crew that water is FREE!

Seats are small but newly redesigned.

ORD
RSW
Good 6.0

Crew was super nice

Delayed 3 hours, boarded and was told would be another 30minutes because of mechanical issues.

BUF
MCO
Mediocre 3.3

The service was Ok, but our flight was 4 hours delayed and it wasn't mechanical or weather related delay, the airline made a scheduling error, we almost missed our car rental and we didn't get to our destination til really late at night when it should been there in the daytime. Overall, won't fly with them again

DCA
DEN
Excellent 8.0

Friendly staff

Didn't like I wasn't offered a cup of water and they nickel and dime you for EVERYTHING!

Mon, Feb 26
ORD
SJU
17h 51m
Mon, Mar 5
SJU
ORD
19h 29m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52727 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
MSY
CLE
Excellent 10.0

Every thing

MSP
MSY
Excellent 10.0

On time

MSP
PHX
Okay 4.0

Flight from MSP to PHX was delayed an hour, which messed up our transportation down there. Minimal word was given, at time of boarding they then delayed 30 min, then when that time expired they added another 30. VERY UNORGINIZED, and unprofessional. Terrible service, terrible airline, don't be tricked by 5% cheaper fairs... they suck!

They canceled our flight home from PHX to MSP, they blamed weather in DFW, which is bull, there were many other airlines flying out of DFW that morning. Because they blamed weather, there was no compensation for screwed up schedules. The next available flight was 2.5 DAYS later!! no other options, it was ridiculous... they were no help to get rebooked on another airline, or even driving to another airport... horrible all around. We ended up driving to Mesa Gateway, flying Alegiant Air to Fargo, renting a car, driving 5.5 hours back to MSP to get our car, then 2.5 hours home again. But it's all good, Spirit refunded that leg of our fare... $220... we spent over $750 to get home by 1am, when we should have been there by early afternoon. DONT EVER FLY SPIRIT - THEY'RE THE WORST...

PHL
MCO
Okay 5.0

Spirit charges for bags BOTH ways

SEA
LAS
Excellent 9.3

It was clean, and I felt like I got a good deal and the staff was very friendly

The other passengers were interesting... lots of swearing, I wouldn’t take my kids on one of these flights

Wed, Jun 6
ORD
SJU
7h 32m
Tue, Jun 12
SJU
ORD
20h 45m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Jun 7
ORD
SJU
4h 50m
Thu, Jun 14
SJU
ORD
5h 10m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 37 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
ORD
SJU
Excellent 10.0

It was a good flight. The attendants were courteous and accomodating. There was nothing to complain about.

ORD
SJU
Excellent 10.0

All very happy staff and super professional service.

ORD
SJU
Good 7.6

I very much enjoyed the male flight attendant in coach. He was fun, attentive and very interacting.

I liked all but the seating. Even for coach is too small in my opinion. Pilot flew awesome.

ORD
SJU
Okay 5.0

Not only did we sit on the plane for over an hour before taking off, but on an over four hour flight I was refused water towards the end. When I asked for more than one glass I was rudely told and I quote, "you know what? No. We have other passengers who may want water." Are you kidding me? I sat down feeling scolded and like I asked for something ridiculous. We landed after 2am and most of the passengers were sleeping and I doubt anyone asked for more water since I didn't see the flight attendant move again. Perhaps she was upset that I interrupted her from reading her paper? Extremely displeased with my experience. I

ORD
SJU
Mediocre 2.0

United airlines.. Terrible

Mon, Apr 30
MDW
SJU
6h 22m
Wed, May 9
SJU
MDW
7h 22m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

DTW
YOW
Excellent 9.3

Please see above. Sherry was amazing

Plane was small and older but it was a short flight

ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

MSP
CUN
Mediocre 2.0

nothing

They lost my luggage.

Tue, May 29
ORD
SJU
4h 39m
Sun, Jun 3
SJU
ORD
5h 18m
Trip: 6 days
6.5GoodShow reviews
Overall 6.5 Good
Based on 6 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
ORD
CLT
Mediocre 3.0

Three hours delay. I paid for a upgrade to first class. But because of the flight change i didn't get to keep my upgrade and I had to beg for a refund. I have had two trips in the past 5 days and all flights have been anywhere from 1 to 3 hours late. Worst experience with AA I have had in a long time.

LAS
DFW
Excellent 8.0

Flight was punctual and service was good.

Gate change

PHX
GEG
Good 7.3

The crew was friendly and informative. They were very helpful. The

The seats were uncomfortable. They were hard and so narrow I had to sit crooked in the seat to keep from getting banged into by the service carts and every person going by to the bathrooms. I'm not tiny, but I'm not huge either, it was just overcrowded. It was also very hot in the airplane the entire way from Phoenix to Spokane. My husband, who is always cold, was even hot.

JAX
DFW
Excellent 8.6

Polite. Clean. Nice business class.

Would like more Western food.

SJU
MIA
Excellent 9.3

New onboard entertainment

Wed, Apr 11
ORD
SJU
7h 31m
Tue, Apr 17
SJU
ORD
8h 38m
Trip: 7 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33843 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MCO
CLT
Mediocre 3.3

The flight was ok

First of all the check in lady was rude and unprofessional. The company lost y luggage resulting in extra charges When I was looking for assistance mr Prince was extremely rude, rolling the eyes and not providing support, I was lost and seeking for guidance and I had to figure it out by myself

DCA
DEN
Excellent 8.0

Friendly staff

Didn't like I wasn't offered a cup of water and they nickel and dime you for EVERYTHING!

DEN
ORD
Excellent 9.6

They left me alone.

Fold down tables are tiny

PHL
DEN
Mediocre 2.0

This is actually almost a funny question because Frontier is the worst Airlines well actually that's not true spirit is the worst Airlines the seats are uncomfortable it takes about an hour and a half to just put your bags and baggage drop and then when you get on the plane They don't serve you anything they have no entertainment your crowded in can't move people are rude worst hairlines ever

Every single thing

MKE
TPA
Mediocre 2.0

the flights and attendents were good ,flight was delayed almost 2 hours on my return flight

didnt have to pay for luggage on first flight put under seat on return flight the girl at ticket counter was rude to me and charged me 45.00 for my bag i put under my seat and she was not a pleasant person to deal with, i wouldnt fly frontier again

Wed, Apr 11
ORD
SJU
7h 31m
Tue, Apr 17
SJU
ORD
8h 38m
Trip: 7 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33843 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
IAD
SAT
Mediocre 3.6

The crew was helpful and apologetic.

They purposefully understaffed the check in counter, which you have to use. They charge for every little thing, even carry on bags and snacks. The seats might as well be lawn chairs. They are so close together everyone onboard will die from head injuries if there's an accident. I'll fly Southwest from now on.

PHL
DEN
Mediocre 2.0

This is actually almost a funny question because Frontier is the worst Airlines well actually that's not true spirit is the worst Airlines the seats are uncomfortable it takes about an hour and a half to just put your bags and baggage drop and then when you get on the plane They don't serve you anything they have no entertainment your crowded in can't move people are rude worst hairlines ever

Every single thing

MKE
TPA
Mediocre 2.0

the flights and attendents were good ,flight was delayed almost 2 hours on my return flight

didnt have to pay for luggage on first flight put under seat on return flight the girl at ticket counter was rude to me and charged me 45.00 for my bag i put under my seat and she was not a pleasant person to deal with, i wouldnt fly frontier again

TPA
LAS
Okay 4.3

Very reasonable price.

You literally have to pay for even the basic things, including for seats to recline. Cushion on seats thin and seats don't recline. 5hrs flight and No entertainment, no tv, no radio, no complimentary food...they offered a cup of water.

BUF
MCO
Good 7.3

Flight was great. Checkin etc was great

Tue, May 1
ORD
SJU
7h 32m
Mon, May 7
SJU
ORD
8h 26m
Trip: 7 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33843 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MKE
TPA
Mediocre 2.0

the flights and attendents were good ,flight was delayed almost 2 hours on my return flight

didnt have to pay for luggage on first flight put under seat on return flight the girl at ticket counter was rude to me and charged me 45.00 for my bag i put under my seat and she was not a pleasant person to deal with, i wouldnt fly frontier again

DCA
DEN
Excellent 8.0

Friendly staff

Didn't like I wasn't offered a cup of water and they nickel and dime you for EVERYTHING!

IAD
SAT
Mediocre 3.6

The crew was helpful and apologetic.

They purposefully understaffed the check in counter, which you have to use. They charge for every little thing, even carry on bags and snacks. The seats might as well be lawn chairs. They are so close together everyone onboard will die from head injuries if there's an accident. I'll fly Southwest from now on.

BUF
MCO
Good 7.3

Flight was great. Checkin etc was great

BUF
MCO
Mediocre 3.3

The service was Ok, but our flight was 4 hours delayed and it wasn't mechanical or weather related delay, the airline made a scheduling error, we almost missed our car rental and we didn't get to our destination til really late at night when it should been there in the daytime. Overall, won't fly with them again

Tue, May 1
ORD
SJU
7h 32m
Mon, May 7
SJU
ORD
8h 26m
Trip: 7 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33843 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
TPA
LAS
Okay 4.3

Very reasonable price.

You literally have to pay for even the basic things, including for seats to recline. Cushion on seats thin and seats don't recline. 5hrs flight and No entertainment, no tv, no radio, no complimentary food...they offered a cup of water.

ISP
MIA
Excellent 10.0

Great flight from Islip to MIA. Looked at another review about water on flights and I was told by the crew that water is FREE!

Seats are small but newly redesigned.

MCO
CLT
Mediocre 3.3

The flight was ok

First of all the check in lady was rude and unprofessional. The company lost y luggage resulting in extra charges When I was looking for assistance mr Prince was extremely rude, rolling the eyes and not providing support, I was lost and seeking for guidance and I had to figure it out by myself

BUF
MCO
Mediocre 3.3

The service was Ok, but our flight was 4 hours delayed and it wasn't mechanical or weather related delay, the airline made a scheduling error, we almost missed our car rental and we didn't get to our destination til really late at night when it should been there in the daytime. Overall, won't fly with them again

BUF
MCO
Good 7.3

Flight was great. Checkin etc was great

Tue, Jul 17
ORD
SJU
6h 56m
Mon, Jul 23
SJU
ORD
8h 31m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jun 5
ORD
SJU
7h 32m
Mon, Jun 11
SJU
ORD
8h 32m
Trip: 7 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33843 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MKE
TPA
Mediocre 2.0

the flights and attendents were good ,flight was delayed almost 2 hours on my return flight

didnt have to pay for luggage on first flight put under seat on return flight the girl at ticket counter was rude to me and charged me 45.00 for my bag i put under my seat and she was not a pleasant person to deal with, i wouldnt fly frontier again

DEN
SFO
Mediocre 2.0

The crew was rude to the passengers. They charge form 9$ to 40$ for seat selection. Charge for a Carry on bag (anything that doesn't fit under your seat). The flights had maintenance issue, hence delayed. I will absolutely avoid traveling with frontier in the future.

IAD
SAT
Mediocre 3.6

The crew was helpful and apologetic.

They purposefully understaffed the check in counter, which you have to use. They charge for every little thing, even carry on bags and snacks. The seats might as well be lawn chairs. They are so close together everyone onboard will die from head injuries if there's an accident. I'll fly Southwest from now on.

PHL
DEN
Mediocre 2.0

This is actually almost a funny question because Frontier is the worst Airlines well actually that's not true spirit is the worst Airlines the seats are uncomfortable it takes about an hour and a half to just put your bags and baggage drop and then when you get on the plane They don't serve you anything they have no entertainment your crowded in can't move people are rude worst hairlines ever

Every single thing

ISP
MIA
Excellent 10.0

Great flight from Islip to MIA. Looked at another review about water on flights and I was told by the crew that water is FREE!

Seats are small but newly redesigned.

Tue, Feb 20
ORD
SJU
7h 01m
Tue, Feb 27
SJU
ORD
8h 28m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52727 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
DEN
IAH
Good 6.0

I liked it much better before priceline took over

I don't like the fact that I can no longer print my boarding pass before I get to the airport

PHL
MCO
Okay 5.0

Spirit charges for bags BOTH ways

ORD
LAS
Mediocre 2.0

N/A

The flight ended up canceling. There was no explanation given and no accommodations to reschedule. It was a Friday and the earliest they could fly us out was Sunday, we were scheduled to fly back Monday. There wasn’t even an apology or attempt to get us on another flight. We walked ourselves over to the frontier counter where they were willing to help us figure something out. That flight actually ended up delayed and they gave us vouchers for the delay so we would fly with them again in the future. The airlines are a service industry and spirit gets a 0 in my eyes.

MSY
CLE
Excellent 10.0

Every thing

FLL
MDE
Mediocre 2.0

Nothing

Spirit offers the worst service there is I arrived 1 hour earlier to the flight they wouldn't take my luggage had to purchase my ticket through another airline

Tue, Jun 26
ORD
SJU
7h 32m
Mon, Jul 2
SJU
ORD
8h 31m
Trip: 7 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33843 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MCO
CLT
Mediocre 3.3

The flight was ok

First of all the check in lady was rude and unprofessional. The company lost y luggage resulting in extra charges When I was looking for assistance mr Prince was extremely rude, rolling the eyes and not providing support, I was lost and seeking for guidance and I had to figure it out by myself

ISP
MIA
Excellent 10.0

Great flight from Islip to MIA. Looked at another review about water on flights and I was told by the crew that water is FREE!

Seats are small but newly redesigned.

DCA
DEN
Excellent 8.0

Friendly staff

Didn't like I wasn't offered a cup of water and they nickel and dime you for EVERYTHING!

BUF
MCO
Good 7.3

Flight was great. Checkin etc was great

DEN
ORD
Excellent 9.6

They left me alone.

Fold down tables are tiny

Wed, Jul 4
ORD
SJU
7h 39m
Mon, Jul 9
SJU
ORD
8h 31m
Trip: 6 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33843 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
ISP
MIA
Excellent 10.0

Great flight from Islip to MIA. Looked at another review about water on flights and I was told by the crew that water is FREE!

Seats are small but newly redesigned.

IAD
SAT
Mediocre 3.6

The crew was helpful and apologetic.

They purposefully understaffed the check in counter, which you have to use. They charge for every little thing, even carry on bags and snacks. The seats might as well be lawn chairs. They are so close together everyone onboard will die from head injuries if there's an accident. I'll fly Southwest from now on.

DEN
ORD
Excellent 9.6

They left me alone.

Fold down tables are tiny

PHL
DEN
Mediocre 2.0

This is actually almost a funny question because Frontier is the worst Airlines well actually that's not true spirit is the worst Airlines the seats are uncomfortable it takes about an hour and a half to just put your bags and baggage drop and then when you get on the plane They don't serve you anything they have no entertainment your crowded in can't move people are rude worst hairlines ever

Every single thing

BUF
MCO
Good 7.3

Flight was great. Checkin etc was great

Fri, Mar 16
ORD
SJU
4h 37m
Mon, Mar 19
SJU
ORD
19h 29m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jun 5
MDW
SJU
6h 22m
Mon, Jun 11
SJU
MDW
9h 40m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
DTW
Excellent 10.0

Pls see above

ATL
MEX
Excellent 10.0

Flight was on time, crew was friendly, plane was clean, and boarding was painless and efficient. Food was served which was a huge plus. I appreciate having a choice of almonds for a snack.

ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

BOS
BNA
Excellent 8.0

Service vey Good. Nice choices. Comfort seating very nice

WiFi awful. Useless.

GDL
ATL
Excellent 9.0

Staff was great!

No TV for movies.

Tue, Jul 17
ORD
SJU
7h 39m
Mon, Jul 23
SJU
ORD
8h 31m
Trip: 7 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33843 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
BUF
MCO
Mediocre 3.3

The service was Ok, but our flight was 4 hours delayed and it wasn't mechanical or weather related delay, the airline made a scheduling error, we almost missed our car rental and we didn't get to our destination til really late at night when it should been there in the daytime. Overall, won't fly with them again

DEN
ORD
Excellent 9.6

They left me alone.

Fold down tables are tiny

DCA
DEN
Excellent 8.0

Friendly staff

Didn't like I wasn't offered a cup of water and they nickel and dime you for EVERYTHING!

TPA
LAS
Okay 4.3

Very reasonable price.

You literally have to pay for even the basic things, including for seats to recline. Cushion on seats thin and seats don't recline. 5hrs flight and No entertainment, no tv, no radio, no complimentary food...they offered a cup of water.

ISP
MIA
Excellent 10.0

Great flight from Islip to MIA. Looked at another review about water on flights and I was told by the crew that water is FREE!

Seats are small but newly redesigned.

Tue, Mar 27
ORD
SJU
4h 45m
Tue, Apr 3
SJU
ORD
18h 25m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 37 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
ORD
SJU
Excellent 8.0

Everything ok except the seats

The seats were uncomfortable.

ORD
SJU
Good 6.0

The crew was nice and the flight itself wasn't bad.

Nothing to entertain in the plane on the way to SJU. No snacks for free, it's a 4+ hrs flight without even a bag of pretzels!?

ORD
SJU
Mediocre 2.0

Flight never happened because of hurricane yet I never got my money back. Natural disasters should qualify for a refund not a voucher.

ORD
SJU
Good 7.6

I very much enjoyed the male flight attendant in coach. He was fun, attentive and very interacting.

I liked all but the seating. Even for coach is too small in my opinion. Pilot flew awesome.

ORD
SJU
Excellent 10.0

Smooth ride and on time staff was great

I didn't like that I had to pay for my luggage that was really horrible they find anywhere to nickel and dime you but glad they let mine be a carry on

Sun, Mar 18
ORD
SJU
19h 44m
Thu, Mar 22
SJU
ORD
8h 19m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews

Chicago to San Juan Flight Information

Avg. Flight Duration 4h 59m
Flights Arrive in San Juan
Flights Depart from Chicago
Flight Price $189
Distance 2054 miles
Airlines Frontier, Spirit Airlines, United, Delta, American Airlines
*
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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.