Find Cheap Flights from San Juan to Chicago O'Hare International (PR1 - ORD)

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Book cheap flights from San Juan to Chicago O'Hare International (round-trip)

Airports
Origin
San Juan
$275
only
$275
Destination
Chicago
$275
only
$275
Wed, Feb 7
SJU
ORD
8h 14m
Wed, Feb 14
ORD
SJU
22h 25m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Thu, May 10
SJU
ORD
8h 19m
Sun, May 13
ORD
SJU
6h 49m
Trip: 4 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 51220 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ATL
FLL
Excellent 10.0

Dwight the flight attendant was amazing made the flight the best.

Having to pay 55 for a bag.

MSY
BWI
Excellent 10.0

Everything was just perfect! Boarding and checking in didn’t take long at all which was great.

TPA
ORD
Mediocre 2.0

The plane was very dated. The seats were broken (did not recline). Did arrive on time which was a plus.

Overall Bad Experience

PHX
ORD
Mediocre 3.6

Boarded the aircraft quickly and left on time.

Airplane reeked of vomit and vinegar. Seats were dirty and you have to pay for water.

ORD
LGA
Good 6.3

Flight and gate staff were great

Waited 45 minutes in line to check our bag. Ours was the third or fourth flight of the day. How were the check in staff so far behind so early??

Sat, Apr 28
SJU
ORD
5h 02m
Wed, May 2
ORD
SJU
4h 55m
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
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

PHL
ATL
Okay 5.3

On time

Rude flight attendant

DFW
SCL
Excellent 9.6

The food is very tasty, but AA has not changed the menu in at least one year.

Fri, Jan 12
SJU
ORD
8h 41m
Mon, Jan 15
ORD
SJU
8h 33m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

DTW
BNA
Mediocre 2.0

Sat on the plane on the tarmac for over an hour in the cold...

Thu, Dec 28
SJU
ORD
5h 00m
Sun, Jan 14
ORD
SJU
4h 35m
Trip: 18 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 44 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SJU
ORD
Excellent 10.0

Excelente

SJU
ORD
Excellent 9.0

Had a complimentary drink given to three of us because some rain water leaked in as passengers were boarding the plane. The staff was excellent beyond that!!!

Our flight was late leaving and for some reason when I checked in on my phone it said I needed to see an agent for my seat assignment

SJU
ORD
Mediocre 2.0

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

SJU
ORD
Excellent 10.0

Attendants were very personable and friendly. I loved that they brought multiple rounds of water throughout the flight. Communication was great and no waiting times. Wonderful flight home after a wonderful vacation!

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, Jan 25
SJU
ORD
24h 55m
Mon, Jan 29
ORD
SJU
22h 25m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Jan 29
SJU
ORD
19h 20m
Mon, Feb 5
ORD
SJU
22h 25m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Mar 9
SJU
ORD
5h 35m
Sat, Mar 17
ORD
SJU
4h 29m
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
JFK
MXP
Mediocre 2.6

Plane was old and dirty, seat pocket had junk in it. Seat was broken and couldn’t stay up. In flight movies were from few years back with a center tv and no head rest screen. Crew on overseas flights tend to be older in age and less tolerant..much better on continental on the same route.

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.

SJU
ORD
Okay 5.3

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

CLE
JFK
Mediocre 3.3

Plane was dirty and crew inattentive.

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.

Wed, Mar 14
SJU
ORD
6h 53m
Sun, Mar 18
ORD
SJU
4h 37m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Jun 7
SJU
ORD
7h 53m
Tue, Jun 12
ORD
SJU
6h 49m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Dec 29
SJU
ORD
10h 48m
Fri, Jan 12
ORD
SJU
13h 55m
Trip: 15 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 44 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SJU
ORD
Excellent 10.0

Excelente

SJU
ORD
Excellent 8.0

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

SJU
ORD
Excellent 10.0

Attendants were very personable and friendly. I loved that they brought multiple rounds of water throughout the flight. Communication was great and no waiting times. Wonderful flight home after a wonderful vacation!

SJU
ORD
Good 6.0

The crew Personnel was courtesy and there were friendly.

I didn't like the process of me having either laptop or some kind of computer to see the TV set because I can't afford that and that's why I had to be looking side-to-side to watch TV also changing to Gates when I got to Chicago I had to change three gates C24 B6 and B2 it was too much changes in a short time that has to be improved.

SJU
ORD
Excellent 9.0

Had a complimentary drink given to three of us because some rain water leaked in as passengers were boarding the plane. The staff was excellent beyond that!!!

Our flight was late leaving and for some reason when I checked in on my phone it said I needed to see an agent for my seat assignment

Tue, Dec 26
SJU
ORD
5h 29m
Sun, Dec 31
ORD
SJU
7h 48m
Trip: 6 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
PHL
ATL
Okay 5.3

On time

Rude flight attendant

DFW
SCL
Excellent 9.6

The food is very tasty, but AA has not changed the menu in at least one year.

GRU
JFK
Mediocre 3.6

The only decent point was the food. Not great but at least edible.

Since check in in São Paulo was a complete chaos. There were only 2 people helping on check in (in machines) and these people were still not helping people (like me) with questions about on how to do check in in those machines. On the other hand to dispatch the bags there were almost 8 attendants to receive the bags. Ridiculous! I’ve tried calling American Airlines and Latam several times to assign a seat for me and they swore there were only middle seats but I know how airlines work to make extra money on these seats. At the end, they only gave me a middle seat option and I had to take I.t of course. On the plane I realized there were dozens of empty seats and yet they made sure not give them to me or anyone else. Unbelievable! Unfortunately I still have to use AA on my way back to Brazil. After this, I’ll chose another airlines for sure. Also, the 3,4,3 arrangement is ridiculous: there’s no corridor space making people touching you everything someone passes by your seat. And boy! Those seats are so uncomfortable and there’s no way to incline the chair so you can even have a little rest (because it’s impossible to even sleep on those seats). The crew were simply doing their jobs! No pleasure! No smile! No engaging with anyone unfortunately! They looked miserable and I asked for water and the flight attendant NEVER brought me anything. Seriously! Water is free!

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
PBI
Okay 5.6

Free movies, and crew were helpful once we were in the air

Gate agent did not start forcing check in, which caused delay in boarding. Ground crew did not stock aircraft until 20 minutes after scheduled departure time. and DFW did the usual 20 minute taxi and then 15 minute hold prior to take off.

Fri, Dec 29
SJU
ORD
10h 48m
Mon, Jan 1
ORD
SJU
4h 25m
Trip: 4 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 44 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
SJU
ORD
Excellent 10.0

Excelente

SJU
ORD
Excellent 8.0

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

SJU
ORD
Excellent 10.0

Attendants were very personable and friendly. I loved that they brought multiple rounds of water throughout the flight. Communication was great and no waiting times. Wonderful flight home after a wonderful vacation!

SJU
ORD
Mediocre 2.0

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

SJU
ORD
Excellent 9.0

Had a complimentary drink given to three of us because some rain water leaked in as passengers were boarding the plane. The staff was excellent beyond that!!!

Our flight was late leaving and for some reason when I checked in on my phone it said I needed to see an agent for my seat assignment

Sun, Dec 31
SJU
ORD
9h 32m
Mon, Jan 8
ORD
SJU
16h 01m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Dec 25
SJU
ORD
5h 29m
Wed, Jan 3
ORD
SJU
7h 48m
Trip: 10 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 $$$

DFW
SCL
Excellent 9.6

The food is very tasty, but AA has not changed the menu in at least one year.

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.

PHL
ATL
Okay 5.3

On time

Rude flight attendant

SJU
ORD
Good 7.3

Ok time flight

Entertainment system did not work in all stops

Tue, Jan 2
SJU
ORD
18h 05m
Sun, Jan 7
ORD
SJU
6h 58m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Dec 17
SJU
ORD
18h 06m
Sat, Dec 23
ORD
SJU
14h 10m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
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