Find Cheap Flights from Puerto Rico to Chicago

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Tue 12/19
Tue 12/26
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Book cheap flights from Puerto Rico to Chicago (round-trip)

Airports
Origin
Aguadilla
$203
only
$203
San Juan
$261
only
$261
Destination
Chicago
$203
only
$203
Tue, Mar 27
BQN
ORD
8h 43m
Tue, Apr 3
ORD
BQN
7h 03m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 51290 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
DTW
BWI
Excellent 8.0

Flight was smooth, and we arrived ahead of schedule!

IAH
EWR
Excellent 10.0

I have flown with Spirit multiple times and I consistently have a fantastic experience. I sincerely have no complaints.

LAS
ORD
Good 6.0

Was happy the plain left the gate right on time and staff was very friendly

When we landed in Chicago there was and other plain in our gate and even with landing 25 minutes early we still got off the plain 30 minutes late

MCO
BWI
Mediocre 2.0

They cancelled the fight after 3 hours of delays while on the tarmac

IAH
LAX
Excellent 10.0

Flight was good and on time. Crew was very nice

The little add ons for luggage, etc

Tue, Feb 27
SJU
ORD
6h 50m
Wed, Feb 28
ORD
SJU
6h 41m
Trip: 2 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
MBJ
JFK
Excellent 9.6

Crew was excellent, had a lot of fun with the vacation crowd on their way back to reality

UIO
FLL
Okay 4.0

One of the flight attendants who stood at the front of the aircraft during boarding did not help us with our luggage placement in the overhead bins by our seats in row two. As a result we had to place one carry on several rows back which did, of course, make it difficult to get to upon landing. Subsequent to that, that same flight attendant helped a young man with his carry on with placement directly above his seat in the first row.Later on, I asked the same flight attendant if I could have some hot water for my wife (helps her with breathing). He came to me with a full cup of very hot, almost scalding, water and a small bottle of water. He did say that the water was very hot, but did not offer any ice to cool it. Naturally, we had no place to partially empty the cup and had to hold it for some time to let it cool. I did ask again for cooler water, but he said none was available.

JFK
CLT
Mediocre 2.0

I asked for help to check in luggage as my flight was leaving soon and I was essentially just told look for any son that stays check in without being directed. After 3 kiosks said put pf service and the lines were packed, when I asked for help again the jet blue advocate said “I can’t help you, you just missed the flight

I missed flight had to call customer service and pay even More money to get to my destination. I’ve been a very loyal jet blue customer both domestic and international and this quite frankly putna bad taste in my mouth

MCO
JFK
Excellent 8.0

Unexpected snacks and a decent variety of drinks.

It was super cold throughout the flight.

BOS
BUF
Excellent 8.6

Even with snow falling in both Boston and Buffalo we managed to only be an hour late.

Tue, Jan 16
SJU
ORD
8h 09m
Tue, Jan 30
ORD
SJU
7h 16m
Trip: 15 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jun 5
BQN
ORD
8h 50m
Tue, Jun 12
ORD
BQN
8h 29m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 51290 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAS
ORD
Good 6.0

Was happy the plain left the gate right on time and staff was very friendly

When we landed in Chicago there was and other plain in our gate and even with landing 25 minutes early we still got off the plain 30 minutes late

SEA
LAS
Okay 5.6

Crew was friendly and nice. Keep me laughing with the jokes. I thought the pilot did a excellent job flying the plane. It was a smooth take off and a smooth landing.

Seats too close togather and I felt like I had no room to move.

IAH
LAX
Excellent 10.0

Flight was good and on time. Crew was very nice

The little add ons for luggage, etc

BOS
PBI
Mediocre 3.6

The fact that the flight was $191.

There was no TVs, charging ports, WiFi. You have to pay for EVERYTHING from your carry on to the water you drink. Seats were uncomfortable. This was my first time flying spirit and would never fly spirit again. Both flights were delayed by maintenance. Staff wasn’t overly exciting for example on the way out the staff was thanked by one guy and he went for a high five and your staff was a stiff and didn’t even high five him back he just looked right passed they guy thanking him. What a loser!

IAH
EWR
Excellent 10.0

I have flown with Spirit multiple times and I consistently have a fantastic experience. I sincerely have no complaints.

Tue, Jun 5
BQN
ORD
8h 50m
Sat, Jun 9
ORD
BQN
8h 29m
Trip: 5 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 51290 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
PHX
Good 6.3

Could not even get a glass of water without having to use credit card

MCO
BWI
Mediocre 2.0

They cancelled the fight after 3 hours of delays while on the tarmac

DFW
ORD
Excellent 10.0

One of the flight attendants on the flight was stunningly beautiful. She made me believe that there is a grand intelligence to the universe and the prime mover is great and terrible

The cramped seating. The fact that i didn't get a chance to gaze upon my beautiful flight attendant once more, only to return to my life having seen true beauty

BOS
PBI
Mediocre 3.6

The fact that the flight was $191.

There was no TVs, charging ports, WiFi. You have to pay for EVERYTHING from your carry on to the water you drink. Seats were uncomfortable. This was my first time flying spirit and would never fly spirit again. Both flights were delayed by maintenance. Staff wasn’t overly exciting for example on the way out the staff was thanked by one guy and he went for a high five and your staff was a stiff and didn’t even high five him back he just looked right passed they guy thanking him. What a loser!

DTW
BWI
Excellent 8.0

Flight was smooth, and we arrived ahead of schedule!

Thu, Jan 25
SJU
ORD
24h 55m
Tue, Jan 30
ORD
SJU
17h 47m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Jun 3
BQN
ORD
8h 50m
Tue, Jun 12
ORD
BQN
8h 29m
Trip: 10 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 51290 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
PHX
Good 6.3

Could not even get a glass of water without having to use credit card

DFW
ORD
Excellent 10.0

One of the flight attendants on the flight was stunningly beautiful. She made me believe that there is a grand intelligence to the universe and the prime mover is great and terrible

The cramped seating. The fact that i didn't get a chance to gaze upon my beautiful flight attendant once more, only to return to my life having seen true beauty

IAH
EWR
Excellent 10.0

I have flown with Spirit multiple times and I consistently have a fantastic experience. I sincerely have no complaints.

ATL
LAX
Good 7.0

We taking off early and arrived early

They charge a lot in baggage too expensive 50$ overweight 30$

DTW
RSW
Mediocre 2.6

Departure late, charges for boarding pass, seats, soda... and those well worn out jokes from the crew: “we charge for smiles”.

Thu, Jan 18
SJU
ORD
6h 47m
Tue, Jan 23
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
MBJ
JFK
Excellent 9.6

Crew was excellent, had a lot of fun with the vacation crowd on their way back to reality

UIO
FLL
Okay 4.0

One of the flight attendants who stood at the front of the aircraft during boarding did not help us with our luggage placement in the overhead bins by our seats in row two. As a result we had to place one carry on several rows back which did, of course, make it difficult to get to upon landing. Subsequent to that, that same flight attendant helped a young man with his carry on with placement directly above his seat in the first row.Later on, I asked the same flight attendant if I could have some hot water for my wife (helps her with breathing). He came to me with a full cup of very hot, almost scalding, water and a small bottle of water. He did say that the water was very hot, but did not offer any ice to cool it. Naturally, we had no place to partially empty the cup and had to hold it for some time to let it cool. I did ask again for cooler water, but he said none was available.

SJU
MCO
Good 7.6

The flight was delayed 30 minutes.

FLL
LGB
Excellent 9.3

The comfortable seating and in flight TV is just excellent.

MCO
JFK
Excellent 8.0

Unexpected snacks and a decent variety of drinks.

It was super cold throughout the flight.

Wed, Jan 17
SJU
ORD
8h 14m
Wed, Jan 24
ORD
SJU
22h 25m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jun 5
BQN
ORD
8h 50m
Thu, Jun 14
ORD
BQN
8h 29m
Trip: 10 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 51290 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAS
ORD
Good 6.0

Was happy the plain left the gate right on time and staff was very friendly

When we landed in Chicago there was and other plain in our gate and even with landing 25 minutes early we still got off the plain 30 minutes late

MCO
BOS
Excellent 10.0

Flight was extremely smooth and on time!

SEA
LAS
Okay 5.6

Crew was friendly and nice. Keep me laughing with the jokes. I thought the pilot did a excellent job flying the plane. It was a smooth take off and a smooth landing.

Seats too close togather and I felt like I had no room to move.

IAH
EWR
Excellent 10.0

I have flown with Spirit multiple times and I consistently have a fantastic experience. I sincerely have no complaints.

DTW
RSW
Mediocre 2.6

Departure late, charges for boarding pass, seats, soda... and those well worn out jokes from the crew: “we charge for smiles”.

Fri, Jan 26
SJU
ORD
6h 47m
Wed, Jan 31
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
BOS
BDA
Good 6.0

When I got home my sneakers were stolen out of my bag They ripped the bag open and stole them

PBI
HPN
Excellent 10.0

Everything

Nothing

UIO
FLL
Okay 4.0

One of the flight attendants who stood at the front of the aircraft during boarding did not help us with our luggage placement in the overhead bins by our seats in row two. As a result we had to place one carry on several rows back which did, of course, make it difficult to get to upon landing. Subsequent to that, that same flight attendant helped a young man with his carry on with placement directly above his seat in the first row.Later on, I asked the same flight attendant if I could have some hot water for my wife (helps her with breathing). He came to me with a full cup of very hot, almost scalding, water and a small bottle of water. He did say that the water was very hot, but did not offer any ice to cool it. Naturally, we had no place to partially empty the cup and had to hold it for some time to let it cool. I did ask again for cooler water, but he said none was available.

SJU
MCO
Good 7.6

The flight was delayed 30 minutes.

MCO
JFK
Excellent 8.0

Unexpected snacks and a decent variety of drinks.

It was super cold throughout the flight.

Thu, Jan 25
SJU
ORD
24h 55m
Thu, Feb 8
ORD
SJU
17h 47m
Trip: 15 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Jun 10
BQN
ORD
8h 50m
Tue, Jun 12
ORD
BQN
8h 29m
Trip: 3 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 51290 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
BOS
PBI
Mediocre 3.6

The fact that the flight was $191.

There was no TVs, charging ports, WiFi. You have to pay for EVERYTHING from your carry on to the water you drink. Seats were uncomfortable. This was my first time flying spirit and would never fly spirit again. Both flights were delayed by maintenance. Staff wasn’t overly exciting for example on the way out the staff was thanked by one guy and he went for a high five and your staff was a stiff and didn’t even high five him back he just looked right passed they guy thanking him. What a loser!

ATL
LAX
Good 7.0

We taking off early and arrived early

They charge a lot in baggage too expensive 50$ overweight 30$

DTW
BWI
Excellent 8.0

Flight was smooth, and we arrived ahead of schedule!

IAH
EWR
Excellent 10.0

I have flown with Spirit multiple times and I consistently have a fantastic experience. I sincerely have no complaints.

DTW
RSW
Mediocre 2.6

Departure late, charges for boarding pass, seats, soda... and those well worn out jokes from the crew: “we charge for smiles”.

Thu, Feb 1
SJU
ORD
6h 47m
Tue, Feb 6
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
BOS
BDA
Good 6.0

When I got home my sneakers were stolen out of my bag They ripped the bag open and stole them

MCO
BWI
Okay 5.3

Plane was 1.5 hours late.

JFK
CLT
Mediocre 2.0

I asked for help to check in luggage as my flight was leaving soon and I was essentially just told look for any son that stays check in without being directed. After 3 kiosks said put pf service and the lines were packed, when I asked for help again the jet blue advocate said “I can’t help you, you just missed the flight

I missed flight had to call customer service and pay even More money to get to my destination. I’ve been a very loyal jet blue customer both domestic and international and this quite frankly putna bad taste in my mouth

FLL
LGB
Excellent 9.3

The comfortable seating and in flight TV is just excellent.

MBJ
JFK
Excellent 9.6

Crew was excellent, had a lot of fun with the vacation crowd on their way back to reality

Tue, Feb 27
SJU
ORD
9h 14m
Tue, Mar 6
ORD
SJU
7h 30m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Feb 6
SJU
ORD
6h 47m
Wed, Mar 7
ORD
SJU
6h 41m
Trip: 30 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
SJU
MCO
Good 7.6

The flight was delayed 30 minutes.

MBJ
JFK
Excellent 9.6

Crew was excellent, had a lot of fun with the vacation crowd on their way back to reality

FLL
LGB
Excellent 9.3

The comfortable seating and in flight TV is just excellent.

FLL
BOS
Excellent 10.0

good leg room, snacks, pleasant flight attendants

nothing

ATL
BOS
Okay 5.0

When I got home and unpacked my sneakers were stolen out of my bag. The ripped the bag open and took them

Sun, Jun 3
BQN
ORD
8h 50m
Mon, Jun 11
ORD
BQN
7h 41m
Trip: 9 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 51290 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
DTW
RSW
Mediocre 2.6

Departure late, charges for boarding pass, seats, soda... and those well worn out jokes from the crew: “we charge for smiles”.

DTW
BWI
Excellent 8.0

Flight was smooth, and we arrived ahead of schedule!

BOS
PBI
Mediocre 3.6

The fact that the flight was $191.

There was no TVs, charging ports, WiFi. You have to pay for EVERYTHING from your carry on to the water you drink. Seats were uncomfortable. This was my first time flying spirit and would never fly spirit again. Both flights were delayed by maintenance. Staff wasn’t overly exciting for example on the way out the staff was thanked by one guy and he went for a high five and your staff was a stiff and didn’t even high five him back he just looked right passed they guy thanking him. What a loser!

IAH
LAX
Excellent 10.0

Flight was good and on time. Crew was very nice

The little add ons for luggage, etc

SEA
LAS
Okay 5.6

Crew was friendly and nice. Keep me laughing with the jokes. I thought the pilot did a excellent job flying the plane. It was a smooth take off and a smooth landing.

Seats too close togather and I felt like I had no room to move.

Wed, Jan 17
SJU
ORD
8h 14m
Mon, Jan 22
ORD
SJU
22h 25m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Feb 7
SJU
ORD
6h 47m
Wed, Mar 7
ORD
SJU
6h 41m
Trip: 29 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
LGB
Excellent 9.3

The comfortable seating and in flight TV is just excellent.

FLL
BOS
Excellent 10.0

good leg room, snacks, pleasant flight attendants

nothing

MCO
BWI
Okay 5.3

Plane was 1.5 hours late.

SJU
MCO
Good 7.6

The flight was delayed 30 minutes.

ATL
BOS
Okay 5.0

When I got home and unpacked my sneakers were stolen out of my bag. The ripped the bag open and took them

Sun, Jun 10
BQN
ORD
8h 50m
Thu, Jun 14
ORD
BQN
8h 29m
Trip: 5 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 51290 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
DFW
ORD
Excellent 10.0

One of the flight attendants on the flight was stunningly beautiful. She made me believe that there is a grand intelligence to the universe and the prime mover is great and terrible

The cramped seating. The fact that i didn't get a chance to gaze upon my beautiful flight attendant once more, only to return to my life having seen true beauty

SEA
LAS
Okay 5.6

Crew was friendly and nice. Keep me laughing with the jokes. I thought the pilot did a excellent job flying the plane. It was a smooth take off and a smooth landing.

Seats too close togather and I felt like I had no room to move.

IAH
EWR
Excellent 10.0

I have flown with Spirit multiple times and I consistently have a fantastic experience. I sincerely have no complaints.

BOS
PBI
Mediocre 3.6

The fact that the flight was $191.

There was no TVs, charging ports, WiFi. You have to pay for EVERYTHING from your carry on to the water you drink. Seats were uncomfortable. This was my first time flying spirit and would never fly spirit again. Both flights were delayed by maintenance. Staff wasn’t overly exciting for example on the way out the staff was thanked by one guy and he went for a high five and your staff was a stiff and didn’t even high five him back he just looked right passed they guy thanking him. What a loser!

DTW
RSW
Mediocre 2.6

Departure late, charges for boarding pass, seats, soda... and those well worn out jokes from the crew: “we charge for smiles”.

*
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