Find Cheap Flights from Chicago to San Jose Juan Santamaria Intl (CHI - SJO)

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Wed 1/17
Wed 1/24
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Good to Know

Low Season:
February
Best time to beat the crowds
3%
expected price decrease
High Season:
July
Most popular time to fly
11%
expected price increase
Average Price:
$512
(avg. price over the last 2 weeks)
Good Deal:
$372
or less (round trip)

When to Book Flights from Chicago to San Jose Juan Santamaria Intl

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $372 or less.
The cheapest flight from Chicago to San Jose Juan Santamaria Intl was found 65 days before departure, on average.
Book at least 3 weeks before departure in order to get a below-average price.
High season is considered to be June, July and August. The cheapest month to fly is February.
Morning departure is around 5% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Chicago to San Jose Juan Santamaria Intl Flights

How long does a flight from Chicago to San Jose Juan Santamaria Intl take?
An average nonstop flight takes 6h 52m, covering a distance of 2213 miles.
How many flights are there between Chicago and San Jose Juan Santamaria Intl?
There is 1 (nonstop) flight between Chicago and San Jose Juan Santamaria Intl per week.
Which airlines provide the cheapest flights from Chicago to San Jose Juan Santamaria Intl?
In the past 3 days, the cheapest round-trip tickets were found on Interjet ($290), Spirit Airlines ($296) and Multiple Airlines ($305).
Do I need a passport to fly between Chicago and San Jose Juan Santamaria Intl?
Yes.
Which airlines fly most frequently between Chicago and San Jose Juan Santamaria Intl?
United (0 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago to San Jose Juan Santamaria Intl?
For Chicago to San Jose Juan Santamaria Intl, Monday is the cheapest day to fly on average and Sunday is the most expensive. Flying from San Jose Juan Santamaria Intl back to Chicago, the best deals are generally found on Tuesday, with Friday being the most expensive.

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

Airports
Origin
Chicago
$290
only
$290
Destination
San Jose
$290
only
$290
Mon, May 14
ORD
SJO
11h 55m
Tue, May 22
SJO
ORD
10h 05m
Trip: 9 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1327 reviews
Overall
7.6
Boarding
7.7
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
JFK
MEX
Okay 5.6

Emergency row seating was very roomy. Staff members were pleasant. Pilots gave great information during flight.

Delayed flight with no information. Snack was atrocious. They did not collect garbage more than once.

JFK
MEX
Mediocre 3.0

That we arrived safely

everything from start to finish.

JFK
MEX
Mediocre 2.0

I was flying to Mexico City on the second day after the snow storm in NY, I couldn't check-in online in advance as its web page said that I had to check in at the desk 3 hrs in advance. When I got to the airport, the line was not very long at the check in desk at first, but moved very very slowly. When I finally got there, I was told my flight had been cancelled and they moved me to a flight 5 days later. While I understand that it is tough for airlines since quite a lot of flights were cancelled the previous day due to the storm, but moving my flight to 5 days later without any email/text communications is totally unacceptable. Or even if they had allowed me to check-in in advance, I could have know the status better before heading to the airport.

JFK
CUN
Excellent 9.6

Line to check in for boarding pass was very long. Took over an hour.

MEX
IAH
Excellent 8.6

Although there is no food other than a small snack, overall I am happy with Interjet

Wed, Apr 4
ORD
SJO
6h 52m
Tue, Apr 10
SJO
ORD
8h 54m
Trip: 7 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52031 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAX
OAK
Mediocre 3.6

It was cheap, that’s for sure. Especially if you fly a lot on their routes and can join their rewards program it’s worth it.

No seat plug; No reclining seats; No TV; No carry on. Unless the circumstances really require it, just fly with someone else

BOS
MCO
Excellent 9.6

good trip, excellent service

food prices

BOS
MCO
Okay 4.3

The crew is really nice and careful..

I’m pregnant and they put me sitting on the back seat with no space and no window, couldn’t even breathe! And the 2 hour delay. $55 for carry on? WTH ?

RSW
MSP
Good 6.0

Price before baggage rip off. They weren't bad by any means but not sure if the savings of 10 to 15 percent was worth it.

Seats are not comfy and it is truly bare bones no frills. Like driving a car with crank roll up windows and a stick shift. But hey it gets you there. Baggage is way overpriced. It would of been the same price on delta with more comfort and in flight entertianment. Live and learn

SDQ
FLL
Mediocre 2.3

At least I got to my destination

Delayed and cancelations are their best suit. They make you believe you paying so little and saving money Then they charge you so much for baggage, seat selection, You get only 40 pound for checked luggage ridiculous. And if you over 1 pound get ready to pay them 40 dollars extra.

Mon, Apr 16
ORD
SJO
7h 17m
Tue, Apr 24
SJO
ORD
16h 25m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Wed, May 2
ORD
SJO
8h 48m
Wed, May 9
SJO
ORD
10h 24m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52031 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
SDQ
FLL
Mediocre 2.3

At least I got to my destination

Delayed and cancelations are their best suit. They make you believe you paying so little and saving money Then they charge you so much for baggage, seat selection, You get only 40 pound for checked luggage ridiculous. And if you over 1 pound get ready to pay them 40 dollars extra.

LAX
ORD
Good 6.0

Fast boarding and on time departure

Lack of complementary food or beverages as well as lack of any entertainment options

FLL
LGA
Okay 4.0

The fact that this company can't even provide FREE water

MCO
BOS
Excellent 9.6

good flight, excellent service

food prices

MYR
LGA
Mediocre 3.6

The staff was friendly

The lack of proper information about Luggage policy end pricing.

Wed, May 23
ORD
SJO
23h 35m
Tue, May 29
SJO
ORD
22h 05m
Trip: 7 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1327 reviews
Overall
7.6
Boarding
7.7
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
JFK
MEX
Mediocre 3.0

That we arrived safely

everything from start to finish.

JFK
MEX
Okay 4.0

plane is new

they delayed from 04:45pm to like 11:15pm, the worst part is, they never tell you when the flight is gonna take off. so we just waited without knowing if we can leave nyc or not. Landed on mexico city airport around 4am local time, and took another hour to finally get out of the gate. btw, the entire mexico city airport is so smelly at that time. first time here, really really bad experience.

JFK
MEX
Mediocre 2.3

Very poor policy alerting and supporting customers when my flight was camcelled due to a snowstorm at JFK. No notice. No meaningful communication as to next flight. Had to visit the airport 3 additional times in person before I was accepted on subsequent flights. Phone customer service offered no help accept to assign a useless ticket for 4 days later. Once on board everything was what you'd expect from a budget flight. Nothing more. Seats were basically metal frames with some fabric attached. Poorer then the usual coach class but nothing I'd really complain about. Also if you order through Kayak, interjet treats you differently then direct customers with 1-2 hour hold times on the phone. You become second class. Kayak does zero advocacy and puts all the work of rescheduling and fighting for a seat on the next plane completely on you. Be aware.

CUN
JFK
Mediocre 2.0

Nothing

Interjet refused to cancel a flight to JFK on January 4th 2018, JFK was closed that day until the next morning because of a Hurricane Blizzard in NYC. All flights to JFK were cancelled that day, nontheless Interjet maintained that our flight was "On Time" even though this was clearly impossible. They obviously refused to cancel the flight so they could run out the clock on their customers, refuse to re-book anyone, force everyone to sleep in the airport overnight til they could sort out their flights home. We were forced to purchase new flights home on a different airline, at great expense. This is a desperate and criminal manipulation of airline regulations, and we do not accept this behavior.

JFK
CUN
Excellent 9.6

Line to check in for boarding pass was very long. Took over an hour.

Tue, Apr 24
ORD
SJO
7h 17m
Tue, May 8
SJO
ORD
16h 25m
Trip: 15 days
Overall 0.0 Poor
Based on 0 reviews
Sun, May 6
ORD
SJO
11h 55m
Wed, May 16
SJO
ORD
10h 05m
Trip: 11 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1327 reviews
Overall
7.6
Boarding
7.7
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
JFK
CUN
Excellent 9.6

Line to check in for boarding pass was very long. Took over an hour.

BJX
TIJ
Excellent 9.3

They certainly upped their food service. The seats are comfortable.

The air conditioning could have been cooler and stronger... several of us were actually breaking a sweat.

JFK
MEX
Okay 4.0

plane is new

they delayed from 04:45pm to like 11:15pm, the worst part is, they never tell you when the flight is gonna take off. so we just waited without knowing if we can leave nyc or not. Landed on mexico city airport around 4am local time, and took another hour to finally get out of the gate. btw, the entire mexico city airport is so smelly at that time. first time here, really really bad experience.

MEX
LAX
Excellent 9.6

Excellent service and comfortable seats, this is my best airline to travel.

JFK
MEX
Mediocre 2.0

I was flying to Mexico City on the second day after the snow storm in NY, I couldn't check-in online in advance as its web page said that I had to check in at the desk 3 hrs in advance. When I got to the airport, the line was not very long at the check in desk at first, but moved very very slowly. When I finally got there, I was told my flight had been cancelled and they moved me to a flight 5 days later. While I understand that it is tough for airlines since quite a lot of flights were cancelled the previous day due to the storm, but moving my flight to 5 days later without any email/text communications is totally unacceptable. Or even if they had allowed me to check-in in advance, I could have know the status better before heading to the airport.

Sat, Apr 28
ORD
SJO
17h 01m
Fri, May 4
SJO
ORD
10h 05m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Mon, May 14
ORD
SJO
11h 55m
Tue, May 29
SJO
ORD
22h 05m
Trip: 16 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1327 reviews
Overall
7.6
Boarding
7.7
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
MEX
LAX
Excellent 9.6

Excellent service and comfortable seats, this is my best airline to travel.

JFK
CUN
Excellent 9.6

Line to check in for boarding pass was very long. Took over an hour.

JFK
MEX
Mediocre 2.3

Very poor policy alerting and supporting customers when my flight was camcelled due to a snowstorm at JFK. No notice. No meaningful communication as to next flight. Had to visit the airport 3 additional times in person before I was accepted on subsequent flights. Phone customer service offered no help accept to assign a useless ticket for 4 days later. Once on board everything was what you'd expect from a budget flight. Nothing more. Seats were basically metal frames with some fabric attached. Poorer then the usual coach class but nothing I'd really complain about. Also if you order through Kayak, interjet treats you differently then direct customers with 1-2 hour hold times on the phone. You become second class. Kayak does zero advocacy and puts all the work of rescheduling and fighting for a seat on the next plane completely on you. Be aware.

CUN
JFK
Mediocre 2.0

Nothing

Interjet refused to cancel a flight to JFK on January 4th 2018, JFK was closed that day until the next morning because of a Hurricane Blizzard in NYC. All flights to JFK were cancelled that day, nontheless Interjet maintained that our flight was "On Time" even though this was clearly impossible. They obviously refused to cancel the flight so they could run out the clock on their customers, refuse to re-book anyone, force everyone to sleep in the airport overnight til they could sort out their flights home. We were forced to purchase new flights home on a different airline, at great expense. This is a desperate and criminal manipulation of airline regulations, and we do not accept this behavior.

JFK
MEX
Okay 4.0

plane is new

they delayed from 04:45pm to like 11:15pm, the worst part is, they never tell you when the flight is gonna take off. so we just waited without knowing if we can leave nyc or not. Landed on mexico city airport around 4am local time, and took another hour to finally get out of the gate. btw, the entire mexico city airport is so smelly at that time. first time here, really really bad experience.

Sun, Apr 15
ORD
SJO
7h 17m
Thu, Apr 19
SJO
ORD
16h 25m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Tue, May 29
ORD
SJO
11h 55m
Wed, Jun 6
SJO
ORD
10h 05m
Trip: 9 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1327 reviews
Overall
7.6
Boarding
7.7
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
MEX
IAH
Excellent 8.6

Although there is no food other than a small snack, overall I am happy with Interjet

CUN
JFK
Mediocre 2.0

Nothing

Interjet refused to cancel a flight to JFK on January 4th 2018, JFK was closed that day until the next morning because of a Hurricane Blizzard in NYC. All flights to JFK were cancelled that day, nontheless Interjet maintained that our flight was "On Time" even though this was clearly impossible. They obviously refused to cancel the flight so they could run out the clock on their customers, refuse to re-book anyone, force everyone to sleep in the airport overnight til they could sort out their flights home. We were forced to purchase new flights home on a different airline, at great expense. This is a desperate and criminal manipulation of airline regulations, and we do not accept this behavior.

JFK
MEX
Okay 5.6

Emergency row seating was very roomy. Staff members were pleasant. Pilots gave great information during flight.

Delayed flight with no information. Snack was atrocious. They did not collect garbage more than once.

MEX
LAX
Excellent 9.6

Excellent service and comfortable seats, this is my best airline to travel.

JFK
MEX
Mediocre 3.0

That we arrived safely

everything from start to finish.

Sun, Apr 22
ORD
SJO
7h 17m
Wed, Apr 25
SJO
ORD
16h 25m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Apr 10
ORD
SJO
11h 55m
Wed, Apr 18
SJO
ORD
16h 25m
Trip: 9 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1327 reviews
Overall
7.6
Boarding
7.7
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
MEX
LAX
Excellent 9.6

Excellent service and comfortable seats, this is my best airline to travel.

JFK
MEX
Mediocre 2.0

I was flying to Mexico City on the second day after the snow storm in NY, I couldn't check-in online in advance as its web page said that I had to check in at the desk 3 hrs in advance. When I got to the airport, the line was not very long at the check in desk at first, but moved very very slowly. When I finally got there, I was told my flight had been cancelled and they moved me to a flight 5 days later. While I understand that it is tough for airlines since quite a lot of flights were cancelled the previous day due to the storm, but moving my flight to 5 days later without any email/text communications is totally unacceptable. Or even if they had allowed me to check-in in advance, I could have know the status better before heading to the airport.

JFK
MEX
Mediocre 2.3

Very poor policy alerting and supporting customers when my flight was camcelled due to a snowstorm at JFK. No notice. No meaningful communication as to next flight. Had to visit the airport 3 additional times in person before I was accepted on subsequent flights. Phone customer service offered no help accept to assign a useless ticket for 4 days later. Once on board everything was what you'd expect from a budget flight. Nothing more. Seats were basically metal frames with some fabric attached. Poorer then the usual coach class but nothing I'd really complain about. Also if you order through Kayak, interjet treats you differently then direct customers with 1-2 hour hold times on the phone. You become second class. Kayak does zero advocacy and puts all the work of rescheduling and fighting for a seat on the next plane completely on you. Be aware.

MEX
DFW
Excellent 10.0

Everything was great! Thanks

CUN
JFK
Mediocre 2.0

Nothing

Interjet refused to cancel a flight to JFK on January 4th 2018, JFK was closed that day until the next morning because of a Hurricane Blizzard in NYC. All flights to JFK were cancelled that day, nontheless Interjet maintained that our flight was "On Time" even though this was clearly impossible. They obviously refused to cancel the flight so they could run out the clock on their customers, refuse to re-book anyone, force everyone to sleep in the airport overnight til they could sort out their flights home. We were forced to purchase new flights home on a different airline, at great expense. This is a desperate and criminal manipulation of airline regulations, and we do not accept this behavior.

Sun, Apr 22
ORD
SJO
7h 17m
Wed, Apr 25
SJO
ORD
16h 25m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Jun 1
ORD
SJO
13h 50m
Wed, Jun 6
SJO
ORD
16h 25m
Trip: 6 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1327 reviews
Overall
7.6
Boarding
7.7
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
YVR
CUN
Excellent 10.0

The whole experience! Customer service was excellent and the staff were very polite, helpful and curtious. We were apprehensive (because it is a new company) we are so happy we decided to book with Interjet. We will be sure to fly with Interjet again!!

We wish you had more destinations. We would have booked our return flight but we are flying out of Merida Mexico. We are considering taking a bus back to Cancun so we can fly back to Vancouver BC Canada but we will wait and see. The check in baggage price seemed high but we take that back as we were both allowed our carry-on without a fee, so $34.00 was more than fair! Thank you for such great service! Sincerely, Donald Dale Meier and Cindy Erskine

JFK
CUN
Excellent 9.6

Line to check in for boarding pass was very long. Took over an hour.

MEX
LAX
Excellent 9.6

Excellent service and comfortable seats, this is my best airline to travel.

JFK
MEX
Okay 5.6

Emergency row seating was very roomy. Staff members were pleasant. Pilots gave great information during flight.

Delayed flight with no information. Snack was atrocious. They did not collect garbage more than once.

JFK
MEX
Mediocre 2.0

I was flying to Mexico City on the second day after the snow storm in NY, I couldn't check-in online in advance as its web page said that I had to check in at the desk 3 hrs in advance. When I got to the airport, the line was not very long at the check in desk at first, but moved very very slowly. When I finally got there, I was told my flight had been cancelled and they moved me to a flight 5 days later. While I understand that it is tough for airlines since quite a lot of flights were cancelled the previous day due to the storm, but moving my flight to 5 days later without any email/text communications is totally unacceptable. Or even if they had allowed me to check-in in advance, I could have know the status better before heading to the airport.

Sat, Apr 28
ORD
SJO
17h 01m
Sun, May 27
SJO
ORD
20h 05m
Trip: 30 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Jun 3
ORD
SJO
11h 55m
Fri, Jun 8
SJO
ORD
10h 05m
Trip: 6 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1327 reviews
Overall
7.6
Boarding
7.7
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
JFK
MEX
Mediocre 2.3

Very poor policy alerting and supporting customers when my flight was camcelled due to a snowstorm at JFK. No notice. No meaningful communication as to next flight. Had to visit the airport 3 additional times in person before I was accepted on subsequent flights. Phone customer service offered no help accept to assign a useless ticket for 4 days later. Once on board everything was what you'd expect from a budget flight. Nothing more. Seats were basically metal frames with some fabric attached. Poorer then the usual coach class but nothing I'd really complain about. Also if you order through Kayak, interjet treats you differently then direct customers with 1-2 hour hold times on the phone. You become second class. Kayak does zero advocacy and puts all the work of rescheduling and fighting for a seat on the next plane completely on you. Be aware.

MEX
IAH
Excellent 8.6

Although there is no food other than a small snack, overall I am happy with Interjet

CUN
JFK
Mediocre 2.0

Nothing

Interjet refused to cancel a flight to JFK on January 4th 2018, JFK was closed that day until the next morning because of a Hurricane Blizzard in NYC. All flights to JFK were cancelled that day, nontheless Interjet maintained that our flight was "On Time" even though this was clearly impossible. They obviously refused to cancel the flight so they could run out the clock on their customers, refuse to re-book anyone, force everyone to sleep in the airport overnight til they could sort out their flights home. We were forced to purchase new flights home on a different airline, at great expense. This is a desperate and criminal manipulation of airline regulations, and we do not accept this behavior.

BJX
TIJ
Excellent 9.3

They certainly upped their food service. The seats are comfortable.

The air conditioning could have been cooler and stronger... several of us were actually breaking a sweat.

JFK
MEX
Mediocre 3.0

That we arrived safely

everything from start to finish.

Sun, Apr 29
ORD
SJO
7h 17m
Sat, May 5
SJO
ORD
16h 25m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jun 12
ORD
SJO
11h 55m
Mon, Jun 18
SJO
ORD
16h 25m
Trip: 7 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1327 reviews
Overall
7.6
Boarding
7.7
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
JFK
MEX
Mediocre 2.0

I was flying to Mexico City on the second day after the snow storm in NY, I couldn't check-in online in advance as its web page said that I had to check in at the desk 3 hrs in advance. When I got to the airport, the line was not very long at the check in desk at first, but moved very very slowly. When I finally got there, I was told my flight had been cancelled and they moved me to a flight 5 days later. While I understand that it is tough for airlines since quite a lot of flights were cancelled the previous day due to the storm, but moving my flight to 5 days later without any email/text communications is totally unacceptable. Or even if they had allowed me to check-in in advance, I could have know the status better before heading to the airport.

MEX
DFW
Excellent 10.0

Everything was great! Thanks

YVR
CUN
Excellent 10.0

The whole experience! Customer service was excellent and the staff were very polite, helpful and curtious. We were apprehensive (because it is a new company) we are so happy we decided to book with Interjet. We will be sure to fly with Interjet again!!

We wish you had more destinations. We would have booked our return flight but we are flying out of Merida Mexico. We are considering taking a bus back to Cancun so we can fly back to Vancouver BC Canada but we will wait and see. The check in baggage price seemed high but we take that back as we were both allowed our carry-on without a fee, so $34.00 was more than fair! Thank you for such great service! Sincerely, Donald Dale Meier and Cindy Erskine

JFK
CUN
Excellent 9.6

Line to check in for boarding pass was very long. Took over an hour.

JFK
MEX
Okay 5.6

Emergency row seating was very roomy. Staff members were pleasant. Pilots gave great information during flight.

Delayed flight with no information. Snack was atrocious. They did not collect garbage more than once.

Thu, May 10
ORD
SJO
8h 11m
Wed, May 16
SJO
ORD
10h 05m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
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Chicago to San Jose Juan Santamaria Intl Flight Information

Flights Arrive in San Jose Juan Santamaria Intl
Flights Depart from Chicago
Flight Price $290
Distance 2213 miles
Airlines Interjet, Spirit Airlines