Find Cheap Flights from Puerto Rico to Chicago O'Hare International

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Sat 11/18
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Book cheap flights from Puerto Rico to Chicago O'Hare International (round-trip)

Airports
Origin
Aguadilla
$203
only
$203
San Juan
$160
only
$160
Ponce
$595
only
$595
Destination
Chicago
$160
only
$160
Tue, Jan 23
SJU
ORD
8h 16m
Tue, Jan 30
ORD
SJU
6h 56m
Trip: 8 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAS
PDX
Mediocre 3.0

Hey, nothing is free. Not even water. So don't buzz through the aisle saying "food & drinks for purchase", no one's buying. Or "you can move up to a roomier seat for $75." instead of marketing that expensive seat, just get this sjow on the road. I just paid $50 to send a carry-on piece of luggage. Nickle-dime ppl to death!

See above!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!////////////////////////

MSY
BWI
Mediocre 2.0

Small seats

LAS
BWI
Mediocre 2.0

Liked the price hated everthiig else

Price

MCO
MSY
Mediocre 3.3

My flight being short

Paying $90 for having one piece of carry on. Not having the option to even pay for WiFi as it’s nonexistent on Spirit’s planes.

TPA
ORD
Excellent 8.0

I liked efective boarding procces. Without delay!

Seats that you can't move on back.

Wed, Jan 10
SJU
ORD
31h 18m
Thu, Jan 25
ORD
SJU
7h 10m
Trip: 16 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Feb 7
SJU
ORD
8h 16m
Sat, Feb 10
ORD
SJU
6h 56m
Trip: 4 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
TPA
ORD
Excellent 8.0

I liked efective boarding procces. Without delay!

Seats that you can't move on back.

MSY
BWI
Mediocre 2.0

Small seats

MCO
ORD
Excellent 10.0

Flight was on time departing and arrival...

Could not lean back in the seats...but the flight was quick so that negates that.

PAP
FLL
Good 7.0

My flight was very smooth, you get very pilot

I have to pay so much for my luggage. .when I get at the airport, it was my time with the spirit air lines....

LAX
DTW
Excellent 10.0

Excellent experience as always. The young crew were very nice and energetic and helpful, I am always happy flying with Spirit.

Nothing.

Fri, Dec 8
SJU
ORD
5h 27m
Mon, Dec 11
ORD
SJU
4h 33m
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 11 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
SJU
ORD
Okay 5.3

The flight attendant was arrogant. This is her job... just for $$$

FAT
DFW
Excellent 10.0

Nice amount of leg room!!!

Nothing

DFW
SDF
Okay 4.6

Considerate flight attendants. Turned lights down for evening flight, so we could get some rest.

Flight was not on time. Time was changed a day prior with no reason explained. No in flight entertainment on this flight.

SJU
ORD
Good 7.3

Ok time flight

Entertainment system did not work in all stops

BDL
CLT
Okay 4.0

No baggage controls from seat 18 to 28 no bags would fit. As we exited all the front rows we're waiting to get there bags stored in back of planes overhead bins. That's just not right, especially when they charge us extra to take a bag for overhead bins storage.

Wed, Dec 6
SJU
ORD
5h 05m
Sun, Dec 10
ORD
SJU
13h 00m
Trip: 5 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 44 reviews
Overall
7.2
Boarding
7.3
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SJU
ORD
Mediocre 3.6

I like the boarding process and the confort.

My birthday was yesterday, August 22, and we were traveling to Atlanta, and at the San Juan airport the flight to Chicago was delayed so we upgrade to first class because we don have enough time to get birthday diner in the stop in Chicago to Atlanta, so the thing was that they didn't have enough meals for the costumers, they were 2 meals short , my husband couldn't eat so we ask for other options and they only had 2 thing that my husband couldn't eat, because they were horrible. So that brought my husband mad, so it was not enjoyable because every time he tried to do something to feel calm again but they couldn't do anything to help us calm down. They keep telling us that it was her mistake that she miscounted and that they didn't give them enough snacks, we didn't had snacks for the rest of the flight it was stressed full. Tomorrow i have to travel again back to Puerto Rico, and im scared that tomorrow will be a horrible day traveling with United, with no space for being comfortable with no food for 9 hours, im worried that the flight is delayed again and that a lost my flight back home, were my dogs are in a hotel till that night so im scared to have to pay another night for my dogs, and I wouldn't be able to pay it. I hope you could help me to figure something out to make this experience more enjoyable my phone number is 7876440442 Zaimee Esteves and Gian K Cruz

SJU
ORD
Excellent 8.0

Chairs, charging stations onboard, courteous flight attendants, onboard entertainment.

SJU
ORD
Mediocre 2.6

Helpful crew

Almost lost my job because of the flight cancellation and delays.

SJU
ORD
Excellent 8.6

United provided excellent service for my return from Puerto Rico to the mainland. Unlike other carriers, United quickly adapted to the reality on the ground and adjusted their schedules accordingly. The result was a safe, comfortable, flight for a very reasonable cost given the very short amount of time I had to make reservations. Thank you!

Seriously? Landing on one end of one terminal and having my connection at the end of another?

SJU
ORD
Mediocre 2.0

The flight attendant was super rude an racist to one of the passengers

Wed, Jan 10
SJU
ORD
6h 53m
Tue, Jan 23
ORD
SJU
6h 56m
Trip: 14 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
TPA
ORD
Excellent 8.0

I liked efective boarding procces. Without delay!

Seats that you can't move on back.

LAS
PDX
Mediocre 3.0

Hey, nothing is free. Not even water. So don't buzz through the aisle saying "food & drinks for purchase", no one's buying. Or "you can move up to a roomier seat for $75." instead of marketing that expensive seat, just get this sjow on the road. I just paid $50 to send a carry-on piece of luggage. Nickle-dime ppl to death!

See above!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!////////////////////////

LAS
BWI
Mediocre 2.0

Liked the price hated everthiig else

Price

LGA
FLL
Okay 4.6

Flight was delayed. They charged for carryon bags, they charged for water.

MSY
BWI
Mediocre 2.0

Small seats

Wed, Feb 14
SJU
ORD
8h 16m
Wed, Feb 28
ORD
SJU
6h 51m
Trip: 15 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
FLL
IAH
Mediocre 3.0

They moved us from the gate to have an "on-time" departure even though we sat on the taxi way for a while. Why do airlines do this? Are on time stats more important than customer comfort and satisfaction. Then they kept the lights on during the entire flight to "sell" their products. Please, give us at least a free glass of water. You are only cheaper than other airlines when you get a $9 fare, which you have to pay to have anyhow. So they are a bare bone airline, but charges are for everything. This airline stinks, I will not be flying them again unless I absolutely have to. I thought United was bad, but they are great compared to Spirit.

PAP
FLL
Good 7.0

My flight was very smooth, you get very pilot

I have to pay so much for my luggage. .when I get at the airport, it was my time with the spirit air lines....

LAS
PDX
Mediocre 3.0

Hey, nothing is free. Not even water. So don't buzz through the aisle saying "food & drinks for purchase", no one's buying. Or "you can move up to a roomier seat for $75." instead of marketing that expensive seat, just get this sjow on the road. I just paid $50 to send a carry-on piece of luggage. Nickle-dime ppl to death!

See above!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!////////////////////////

TPA
ORD
Excellent 8.0

I liked efective boarding procces. Without delay!

Seats that you can't move on back.

LAX
DTW
Excellent 10.0

Excellent experience as always. The young crew were very nice and energetic and helpful, I am always happy flying with Spirit.

Nothing.

Thu, May 10
SJU
ORD
8h 25m
Mon, May 14
ORD
SJU
6h 49m
Trip: 5 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LGA
FLL
Okay 4.6

Flight was delayed. They charged for carryon bags, they charged for water.

LAS
BWI
Mediocre 2.0

Liked the price hated everthiig else

Price

MSY
BWI
Mediocre 2.0

Small seats

LAS
PDX
Mediocre 3.0

Hey, nothing is free. Not even water. So don't buzz through the aisle saying "food & drinks for purchase", no one's buying. Or "you can move up to a roomier seat for $75." instead of marketing that expensive seat, just get this sjow on the road. I just paid $50 to send a carry-on piece of luggage. Nickle-dime ppl to death!

See above!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!////////////////////////

LAX
DTW
Excellent 10.0

Excellent experience as always. The young crew were very nice and energetic and helpful, I am always happy flying with Spirit.

Nothing.

Fri, Mar 2
BQN
ORD
9h 04m
Wed, Mar 7
ORD
BQN
7h 03m
Trip: 6 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 50586 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
MCO
ORD
Excellent 10.0

Flight was on time departing and arrival...

Could not lean back in the seats...but the flight was quick so that negates that.

TPA
ORD
Excellent 8.0

I liked efective boarding procces. Without delay!

Seats that you can't move on back.

MCO
MSY
Mediocre 3.3

My flight being short

Paying $90 for having one piece of carry on. Not having the option to even pay for WiFi as it’s nonexistent on Spirit’s planes.

FLL
IAH
Mediocre 3.0

They moved us from the gate to have an "on-time" departure even though we sat on the taxi way for a while. Why do airlines do this? Are on time stats more important than customer comfort and satisfaction. Then they kept the lights on during the entire flight to "sell" their products. Please, give us at least a free glass of water. You are only cheaper than other airlines when you get a $9 fare, which you have to pay to have anyhow. So they are a bare bone airline, but charges are for everything. This airline stinks, I will not be flying them again unless I absolutely have to. I thought United was bad, but they are great compared to Spirit.

LAS
PDX
Mediocre 3.0

Hey, nothing is free. Not even water. So don't buzz through the aisle saying "food & drinks for purchase", no one's buying. Or "you can move up to a roomier seat for $75." instead of marketing that expensive seat, just get this sjow on the road. I just paid $50 to send a carry-on piece of luggage. Nickle-dime ppl to death!

See above!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!////////////////////////

Fri, Dec 8
BQN
ORD
13h 47m
Sun, Dec 10
ORD
BQN
9h 22m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Dec 25
SJU
ORD
5h 29m
Mon, Jan 1
ORD
SJU
4h 33m
Trip: 8 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 11 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
FAT
DFW
Excellent 10.0

Nice amount of leg room!!!

Nothing

DFW
SDF
Okay 4.6

Considerate flight attendants. Turned lights down for evening flight, so we could get some rest.

Flight was not on time. Time was changed a day prior with no reason explained. No in flight entertainment on this flight.

SJU
ORD
Okay 4.6

I traveled with this carry on for numerous flights and for the last three legs of this trip w/of having to check it. For some reason they made me check it. because I had to spend time at the baggage claim carousels I almost missed the last train of the night back home. Fortunately all is fine, but it caused unnecessary stress.

PWM
PHL
Okay 4.6

We arrived on time.

These planes feel like they are made of Legos. They are absurdly tiny and uncomfortable (and I am a small woman). Hot and stinky when boarding and no room for you or your carry on luggage. The days of glamorous air travel seem very far away.

CHO
ORD
Good 7.6

It was a little hot in the plane at during start and touchdown

Fri, May 25
SJU
ORD
6h 45m
Thu, May 31
ORD
SJU
6h 49m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Dec 7
SJU
ORD
11h 34m
Sun, Dec 10
ORD
SJU
14h 59m
Trip: 4 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 44 reviews
Overall
7.2
Boarding
7.3
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SJU
ORD
Excellent 8.6

United provided excellent service for my return from Puerto Rico to the mainland. Unlike other carriers, United quickly adapted to the reality on the ground and adjusted their schedules accordingly. The result was a safe, comfortable, flight for a very reasonable cost given the very short amount of time I had to make reservations. Thank you!

Seriously? Landing on one end of one terminal and having my connection at the end of another?

SJU
ORD
Mediocre 2.0

The flight attendant was super rude an racist to one of the passengers

SJU
ORD
Good 7.6

The seats didn't bend back to be comfortable. Only 1 inch!!! The back was restless

SJU
ORD
Excellent 8.0

That you have to pay for a movie and snacks.

SJU
ORD
Mediocre 3.6

I like the boarding process and the confort.

My birthday was yesterday, August 22, and we were traveling to Atlanta, and at the San Juan airport the flight to Chicago was delayed so we upgrade to first class because we don have enough time to get birthday diner in the stop in Chicago to Atlanta, so the thing was that they didn't have enough meals for the costumers, they were 2 meals short , my husband couldn't eat so we ask for other options and they only had 2 thing that my husband couldn't eat, because they were horrible. So that brought my husband mad, so it was not enjoyable because every time he tried to do something to feel calm again but they couldn't do anything to help us calm down. They keep telling us that it was her mistake that she miscounted and that they didn't give them enough snacks, we didn't had snacks for the rest of the flight it was stressed full. Tomorrow i have to travel again back to Puerto Rico, and im scared that tomorrow will be a horrible day traveling with United, with no space for being comfortable with no food for 9 hours, im worried that the flight is delayed again and that a lost my flight back home, were my dogs are in a hotel till that night so im scared to have to pay another night for my dogs, and I wouldn't be able to pay it. I hope you could help me to figure something out to make this experience more enjoyable my phone number is 7876440442 Zaimee Esteves and Gian K Cruz

Fri, Mar 9
SJU
ORD
5h 02m
Mon, Mar 12
ORD
SJU
4h 55m
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 11 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
SJU
ORD
Excellent 8.0

The food and getting a better plane when our flight was switched going to San Juan.

That we sat on the plane for an hour when we could have just walked to a gate so most people wouldn't miss their connecting flight.

FAT
DFW
Excellent 10.0

Nice amount of leg room!!!

Nothing

CHO
ORD
Good 7.6

It was a little hot in the plane at during start and touchdown

PWM
PHL
Okay 4.6

We arrived on time.

These planes feel like they are made of Legos. They are absurdly tiny and uncomfortable (and I am a small woman). Hot and stinky when boarding and no room for you or your carry on luggage. The days of glamorous air travel seem very far away.

BDL
CLT
Okay 4.0

No baggage controls from seat 18 to 28 no bags would fit. As we exited all the front rows we're waiting to get there bags stored in back of planes overhead bins. That's just not right, especially when they charge us extra to take a bag for overhead bins storage.

Mon, Dec 25
SJU
ORD
5h 29m
Sun, Dec 31
ORD
SJU
4h 25m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Apr 8
SJU
ORD
5h 02m
Sat, Apr 14
ORD
SJU
4h 55m
Trip: 7 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 11 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
SJU
ORD
Okay 4.6

I traveled with this carry on for numerous flights and for the last three legs of this trip w/of having to check it. For some reason they made me check it. because I had to spend time at the baggage claim carousels I almost missed the last train of the night back home. Fortunately all is fine, but it caused unnecessary stress.

FAT
DFW
Excellent 10.0

Nice amount of leg room!!!

Nothing

SJU
ORD
Excellent 8.0

The food and getting a better plane when our flight was switched going to San Juan.

That we sat on the plane for an hour when we could have just walked to a gate so most people wouldn't miss their connecting flight.

BDL
CLT
Okay 4.0

No baggage controls from seat 18 to 28 no bags would fit. As we exited all the front rows we're waiting to get there bags stored in back of planes overhead bins. That's just not right, especially when they charge us extra to take a bag for overhead bins storage.

SJU
ORD
Good 7.3

Ok time flight

Entertainment system did not work in all stops

Wed, Nov 22
SJU
ORD
5h 27m
Sun, Dec 3
ORD
SJU
4h 33m
Trip: 12 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 11 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
DFW
SDF
Okay 4.6

Considerate flight attendants. Turned lights down for evening flight, so we could get some rest.

Flight was not on time. Time was changed a day prior with no reason explained. No in flight entertainment on this flight.

SJU
ORD
Excellent 8.0

The food and getting a better plane when our flight was switched going to San Juan.

That we sat on the plane for an hour when we could have just walked to a gate so most people wouldn't miss their connecting flight.

CHO
ORD
Good 7.6

It was a little hot in the plane at during start and touchdown

SJU
ORD
Good 7.3

Ok time flight

Entertainment system did not work in all stops

SJU
ORD
Okay 5.3

The flight attendant was arrogant. This is her job... just for $$$

Thu, May 24
PSE
ORD
14h 12m
Mon, May 28
ORD
PSE
17h 34m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Dec 23
BQN
ORD
11h 14m
Sun, Jan 7
ORD
BQN
9h 22m
Trip: 16 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Apr 18
PSE
ORD
17h 46m
Sun, Apr 22
ORD
PSE
16h 30m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
*
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