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

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

Airports
Origin
San Juan
$231
only
$231
Destination
Chicago
$231
only
$231
Thu, Feb 1
SJU
ORD
8h 14m
Tue, Feb 6
ORD
SJU
10h 24m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jun 5
SJU
ORD
6h 45m
Wed, Jun 6
ORD
SJU
6h 24m
Trip: 2 days
9.3ExcellentShow reviews
Overall 9.3 Excellent
Based on 4 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
MCO
SLC
Excellent 9.3

Crew was polite at the gate and on board. Flight went smoothly, temp was comfortable. Love the individual screens for all.

My sons tv screen wasn't working. I pushed the attendant button to see if they could help, nobody ever came. I left in on for quite awhile too. Wi Fi was hard to log into.

JFK
LAX
Excellent 10.0

Food and drink provided on flight. That's amazing!

Nothing :)

FLL
SAN
Excellent 10.0

I love JetBlue. I love everything about the airline. I love the free wifi and snacks. The seats are comfortable and I actually have room to lay my head down in economy. I love jet blue so much I am always willing to pay extra to fly with the airline. The customer service is superb and I have never had anything but an extremely possitive experience with this airline.

Nothing to complain about at all. Overall a great airline

SEA
JFK
Good 7.3

crew very unfriemdly

DFW
BOS
Good 7.0

Nice crew, comfortable seats.

Delayed flight, broken TV and terrible boarding process. Frozen toilet chemicals.

Tue, Feb 13
SJU
ORD
5h 10m
Mon, Feb 19
ORD
SJU
4h 37m
Trip: 7 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 45 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SJU
ORD
Excellent 8.0

That you have to pay for a movie and snacks.

SJU
ORD
Good 7.3

My flight did not go to Chicago. United changed our flight without notifying us. Instead we went to DC. Almost missed our plane.

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
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

Thu, Mar 8
SJU
ORD
5h 35m
Mon, Mar 12
ORD
SJU
4h 30m
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
TPA
DFW
Good 6.3

Decent boarding group, same snacks, same flight attendants (who were very nice)

My only gripe is that paying for an assigned seat is only allowed 48 hours before takeoff and costs at least $30, twice what Spirit charges to allow you to select a seat during booking, so it is worse. No one watched us to ensure that we didn’t use the overhead bins (a stipulation of the fare) but we did comply anyway. We chose to take our chances and were assigned seats at the gate 16 rows apart and both in the middle seat.

SFO
LAX
Excellent 10.0

great flight

DFW
PHL
Mediocre 3.0

They separated my bags, so I had to wait in Philadelphia for my bag to arrive on next flight 2 1/2 hours latter. Not happy after flying from Sydney.

SJU
ORD
Okay 5.3

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

DFW
SAT
Okay 5.6

The flight was so short we did not even get a snack, only an offer of a bottle of water; this was simply due to to short length of the flight. Basic economy had my wife and I 16 rows apart each in a middle seat. I was in the very last seat on the plane. Flight attendants were attentive and surprisingly very nice, legroom is non-existent (same as every flight in plain coach).

High cost to prebook seats was twice what Spirit or Frontier would charge

Fri, Jul 6
SJU
ORD
7h 25m
Sat, Jul 14
ORD
SJU
8h 44m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
FLL
Excellent 8.0

When the passenger in front reclines their seat it was in my face The legroom wasn’t terrible but I had a hard time even reading since it was so close

DFW
LGA
Excellent 10.0

Good service, more leg room than American Airlines.

Everything was good.

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

ATL
BWI
Okay 4.6

Snacks & beverages on a 1 hour flight. Very nice crew

Older plane, no entertainment

CUN
ATL
Mediocre 3.6

The crew on board were helpful

Delta staff at airport were unprofessional. They had us spend over an hour traveling to a different TSA line because they closed the line we were in. The other line was a 10 minute drive away. Also our bags did not reach philadelphia when we landed at 3 am.

Tue, Mar 6
SJU
ORD
16h 14m
Tue, Mar 13
ORD
SJU
10h 59m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Tue, May 8
SJU
ORD
14h 31m
Wed, May 16
ORD
SJU
12h 28m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Mon, May 14
SJU
ORD
5h 02m
Sun, May 20
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
DFW
PHL
Mediocre 3.0

They separated my bags, so I had to wait in Philadelphia for my bag to arrive on next flight 2 1/2 hours latter. Not happy after flying from Sydney.

SJU
ORD
Good 7.3

Ok time flight

Entertainment system did not work in all stops

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.

BCN
JFK
Mediocre 2.0

NOTHING !! I lost my flight because in the email I received you all put the wrong airline on it and nobody took responsability for it . I ended up paying $311.00 to get the next flight back to Austin .

In the email it was stated that my first flight was with British Airways, so i wasted time making the wrong line . Only to get to the counter and waste more tome trying to find me in the system to then tell me my flight is with American Airline . I double check my email where it clearly shows: 1st flight-British Airway and 2nd flight-American Airline . This is not acceptable, nobody wants to take responsability for sending me the wrong information in the email. Had I know both of my flights were with American Airline I wouldn’t lost my plane because I would make the right line to begin with .

SFO
LAX
Excellent 10.0

great flight

Wed, Mar 28
SJU
ORD
5h 10m
Sun, Apr 1
ORD
SJU
26h 03m
Trip: 5 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 45 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SJU
ORD
Good 7.6

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

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

That you have to pay for a movie and snacks.

SJU
ORD
Excellent 8.0

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

SJU
ORD
Mediocre 2.0

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

Wed, May 23
SJU
ORD
5h 02m
Wed, May 30
ORD
SJU
4h 55m
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
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.

SFO
LAX
Excellent 10.0

great flight

BCN
JFK
Mediocre 2.0

NOTHING !! I lost my flight because in the email I received you all put the wrong airline on it and nobody took responsability for it . I ended up paying $311.00 to get the next flight back to Austin .

In the email it was stated that my first flight was with British Airways, so i wasted time making the wrong line . Only to get to the counter and waste more tome trying to find me in the system to then tell me my flight is with American Airline . I double check my email where it clearly shows: 1st flight-British Airway and 2nd flight-American Airline . This is not acceptable, nobody wants to take responsability for sending me the wrong information in the email. Had I know both of my flights were with American Airline I wouldn’t lost my plane because I would make the right line to begin with .

SJU
ORD
Okay 5.3

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

SJU
ORD
Good 7.3

Todo muy bueno

Mon, Apr 30
SJU
ORD
8h 16m
Wed, May 9
ORD
SJU
12h 28m
Trip: 10 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Mar 7
SJU
ORD
5h 35m
Sun, Mar 11
ORD
SJU
6h 40m
Trip: 5 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
SAT
Okay 5.6

The flight was so short we did not even get a snack, only an offer of a bottle of water; this was simply due to to short length of the flight. Basic economy had my wife and I 16 rows apart each in a middle seat. I was in the very last seat on the plane. Flight attendants were attentive and surprisingly very nice, legroom is non-existent (same as every flight in plain coach).

High cost to prebook seats was twice what Spirit or Frontier would charge

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.

SFO
LAX
Excellent 10.0

great flight

SJU
ORD
Good 7.3

Todo muy bueno

JFK
AUS
Mediocre 2.0

I lost money, I came back a day later wish it wasn’t plan and is NOT ok .

kieytcha@gmail.com

Thu, Apr 5
SJU
ORD
5h 10m
Sat, Apr 7
ORD
SJU
4h 37m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jul 11
SJU
ORD
8h 07m
Wed, Jul 18
ORD
SJU
4h 55m
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
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.

DFW
PHL
Mediocre 3.0

They separated my bags, so I had to wait in Philadelphia for my bag to arrive on next flight 2 1/2 hours latter. Not happy after flying from Sydney.

SJU
ORD
Okay 5.3

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

SJU
ORD
Good 7.3

Ok time flight

Entertainment system did not work in all stops

SJU
ORD
Good 7.3

Todo muy bueno

Wed, Jul 18
SJU
ORD
8h 07m
Wed, Jul 25
ORD
SJU
4h 55m
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
SFO
LAX
Excellent 10.0

great 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.

SJU
ORD
Okay 5.3

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

JFK
AUS
Mediocre 2.0

I lost money, I came back a day later wish it wasn’t plan and is NOT ok .

kieytcha@gmail.com

SLC
CLT
Okay 4.0

Flight attendants

The flight got delayed from salt lake and we had to spend a day in Charlotte before another flight came

Fri, Jun 29
SJU
ORD
5h 02m
Sat, Jul 14
ORD
SJU
4h 55m
Trip: 16 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
JFK
AUS
Mediocre 2.0

I lost money, I came back a day later wish it wasn’t plan and is NOT ok .

kieytcha@gmail.com

DFW
SAT
Okay 5.6

The flight was so short we did not even get a snack, only an offer of a bottle of water; this was simply due to to short length of the flight. Basic economy had my wife and I 16 rows apart each in a middle seat. I was in the very last seat on the plane. Flight attendants were attentive and surprisingly very nice, legroom is non-existent (same as every flight in plain coach).

High cost to prebook seats was twice what Spirit or Frontier would charge

SFO
LAX
Excellent 10.0

great 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.

DFW
PHL
Mediocre 3.0

They separated my bags, so I had to wait in Philadelphia for my bag to arrive on next flight 2 1/2 hours latter. Not happy after flying from Sydney.

Thu, Jun 28
SJU
ORD
5h 02m
Sun, Jul 1
ORD
SJU
6h 35m
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
SLC
CLT
Okay 4.0

Flight attendants

The flight got delayed from salt lake and we had to spend a day in Charlotte before another flight came

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.

SJU
ORD
Okay 5.3

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

DFW
PHL
Mediocre 3.0

They separated my bags, so I had to wait in Philadelphia for my bag to arrive on next flight 2 1/2 hours latter. Not happy after flying from Sydney.

JFK
AUS
Mediocre 2.0

I lost money, I came back a day later wish it wasn’t plan and is NOT ok .

kieytcha@gmail.com

Mon, May 21
SJU
ORD
5h 02m
Mon, Jun 4
ORD
SJU
9h 39m
Trip: 15 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
BCN
JFK
Mediocre 2.0

NOTHING !! I lost my flight because in the email I received you all put the wrong airline on it and nobody took responsability for it . I ended up paying $311.00 to get the next flight back to Austin .

In the email it was stated that my first flight was with British Airways, so i wasted time making the wrong line . Only to get to the counter and waste more tome trying to find me in the system to then tell me my flight is with American Airline . I double check my email where it clearly shows: 1st flight-British Airway and 2nd flight-American Airline . This is not acceptable, nobody wants to take responsability for sending me the wrong information in the email. Had I know both of my flights were with American Airline I wouldn’t lost my plane because I would make the right line to begin with .

DFW
PHL
Mediocre 3.0

They separated my bags, so I had to wait in Philadelphia for my bag to arrive on next flight 2 1/2 hours latter. Not happy after flying from Sydney.

DFW
SAT
Okay 5.6

The flight was so short we did not even get a snack, only an offer of a bottle of water; this was simply due to to short length of the flight. Basic economy had my wife and I 16 rows apart each in a middle seat. I was in the very last seat on the plane. Flight attendants were attentive and surprisingly very nice, legroom is non-existent (same as every flight in plain coach).

High cost to prebook seats was twice what Spirit or Frontier would charge

TPA
DFW
Good 6.3

Decent boarding group, same snacks, same flight attendants (who were very nice)

My only gripe is that paying for an assigned seat is only allowed 48 hours before takeoff and costs at least $30, twice what Spirit charges to allow you to select a seat during booking, so it is worse. No one watched us to ensure that we didn’t use the overhead bins (a stipulation of the fare) but we did comply anyway. We chose to take our chances and were assigned seats at the gate 16 rows apart and both in the middle seat.

SJU
ORD
Good 7.3

Todo muy bueno

Mon, Jan 29
SJU
ORD
5h 35m
Sun, Feb 11
ORD
SJU
4h 35m
Trip: 14 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
SLC
CLT
Okay 4.0

Flight attendants

The flight got delayed from salt lake and we had to spend a day in Charlotte before another flight came

DFW
SAT
Okay 5.6

The flight was so short we did not even get a snack, only an offer of a bottle of water; this was simply due to to short length of the flight. Basic economy had my wife and I 16 rows apart each in a middle seat. I was in the very last seat on the plane. Flight attendants were attentive and surprisingly very nice, legroom is non-existent (same as every flight in plain coach).

High cost to prebook seats was twice what Spirit or Frontier would charge

SJU
ORD
Good 7.3

Todo muy bueno

JFK
AUS
Mediocre 2.0

I lost money, I came back a day later wish it wasn’t plan and is NOT ok .

kieytcha@gmail.com

SFO
LAX
Excellent 10.0

great flight

Puerto Rico to Chicago O'Hare International Flight Information

Flights Arrive in Chicago O'Hare International
Flights Depart from Puerto Rico
Flight Price $231
Airlines JetBlue, United, American Airlines, Delta
*
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