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

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Sat 11/18
Sat 11/25
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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:
$583
(avg. price over the last 2 weeks)
Good Deal:
$583
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

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 10% 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 37m, covering a distance of 2213 miles.
How many flights are there between Chicago and San Jose Juan Santamaria Intl?
There are 3 (nonstop) flights between Chicago and San Jose Juan Santamaria Intl per week, averaging 0 per day.
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 Spirit Airlines ($302), Interjet ($318) and Multiple Airlines ($341).
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, Tuesday 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 Sunday, with Saturday being the most expensive.

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

Airports
Origin
Chicago
$302
only
$302
Destination
San Jose
$302
only
$302
Tue, Feb 6
ORD
SJO
6h 37m
Tue, Feb 13
SJO
ORD
9h 05m
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
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
BWI
Mediocre 2.0

Liked the price hated everthiig else

Price

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.

LGA
FLL
Okay 4.6

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

LAS
CLE
Excellent 10.0

zero problems

all great

Wed, Mar 7
ORD
SJO
9h 55m
Wed, Mar 14
SJO
ORD
17h 20m
Trip: 7 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1140 reviews
Overall
7.6
Boarding
7.6
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
MEX
JFK
Excellent 8.0

Pay for ny luggage

OAX
MEX
Excellent 10.0

Staff was great, from check in to boarding and flight. First time flying Interjet and was pleasantly surprised. Every one was helpful and pleasant. On time. Did not expect beverage service on such a short flight.

Carry on Weight was to low. Luggage understandable but not personal handbag

BJX
MEX
Excellent 9.3

Clean, timely flight.

Connecting flight cancelled due to flight departure changes with initial flight. Cancellation policy is outrageous. Spent 3 hours making phone calls and super long hold times and spent time going around in circles.

LAX
MEX
Excellent 8.3

Great experience! We checked in quickly and the they boRded is all on time and also took off on time. The cherry on top was the fact we got to our destination 30mons early. Very easy to work with and efficient

The plane is bare bones. You won’t have the new updates like phone chargers, personal screens, or WiFi

SLP
MEX
Excellent 10.0

Roomy seats, nice staff, clean plane.

Always close to 1 hour late.

Thu, Jan 11
ORD
SJO
9h 55m
Wed, Jan 31
SJO
ORD
10h 10m
Trip: 21 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Feb 3
ORD
SJO
30h 37m
Sat, Feb 10
SJO
ORD
45h 50m
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
IAH
LAS
Mediocre 3.0

Nothing to like really. Crew gathered in galley area, eating & drinking. Crew did not attend to passengers who were swinging feet & legs out in the aisle, pick up trash or other.

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.

DEN
LAS
Okay 5.0

Baggage policy should be more clearly advertised on the site. I could have booked a more expensive flight with a carry on included for less than what Spirit charges for flight and $50 for carry on.

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!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!////////////////////////

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....

Wed, Feb 28
ORD
SJO
11h 40m
Mon, Mar 12
SJO
ORD
10h 10m
Trip: 12 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1140 reviews
Overall
7.6
Boarding
7.6
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
JFK
MEX
Good 6.0

Increíble que no se pueda hacer en vuelos internacionales ni a través de la app

MEX
SAT
Mediocre 2.6

The check in is very Solw. They have to prepare the personnel

MEX
JFK
Excellent 8.0

Pay for ny luggage

GDL
MEX
Excellent 9.3

Flight delayed

LAS
MTY
Excellent 10.0

Everything

?

Sat, Feb 10
ORD
SJO
19h 47m
Sun, Feb 11
SJO
ORD
21h 50m
Trip: 2 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
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.

DEN
LAS
Okay 5.0

Baggage policy should be more clearly advertised on the site. I could have booked a more expensive flight with a carry on included for less than what Spirit charges for flight and $50 for carry on.

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
CLE
Excellent 10.0

zero problems

all great

LAS
BWI
Mediocre 2.0

Liked the price hated everthiig else

Price

Wed, Feb 7
ORD
SJO
23h 40m
Tue, Feb 13
SJO
ORD
8h 51m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Mar 2
ORD
SJO
13h 35m
Fri, Mar 9
SJO
ORD
29h 15m
Trip: 8 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1140 reviews
Overall
7.6
Boarding
7.6
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
JFK
MEX
Excellent 10.0

Took off earlier than expected. Great snacks and drinks. Staff and flight attendants were very courteous and attentive. Great price on tickets as well.

LAS
MTY
Excellent 10.0

Everything

?

BJX
MEX
Excellent 9.3

Clean, timely flight.

Connecting flight cancelled due to flight departure changes with initial flight. Cancellation policy is outrageous. Spent 3 hours making phone calls and super long hold times and spent time going around in circles.

MEX
PVR
Mediocre 2.0

None

Everything. Airline changed departure times on both flights. 50 minutes between connect flights. No other option but to cancel flight from Mexico City to Puerto Vallarta. Had to book a flight with another airline for an additional $300. Cancellation policy is terrible. Not my fault and had no other option.

MEX
JFK
Mediocre 3.3

No entertainment they charged me double to change my departure, I had made an error on date.

Sat, Mar 3
ORD
SJO
6h 52m
Fri, Mar 9
SJO
ORD
29h 15m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Feb 7
ORD
SJO
19h 47m
Tue, Feb 13
SJO
ORD
21h 50m
Trip: 7 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.

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!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!////////////////////////

IAH
LAS
Mediocre 3.0

Nothing to like really. Crew gathered in galley area, eating & drinking. Crew did not attend to passengers who were swinging feet & legs out in the aisle, pick up trash or other.

See above.///////////////////////////////////////////

LAS
BWI
Mediocre 2.0

Liked the price hated everthiig else

Price

DEN
LAS
Okay 5.0

Baggage policy should be more clearly advertised on the site. I could have booked a more expensive flight with a carry on included for less than what Spirit charges for flight and $50 for carry on.

Sat, Mar 3
ORD
SJO
13h 35m
Fri, Mar 9
SJO
ORD
29h 15m
Trip: 7 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1140 reviews
Overall
7.6
Boarding
7.6
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
LAX
MEX
Excellent 8.3

Great experience! We checked in quickly and the they boRded is all on time and also took off on time. The cherry on top was the fact we got to our destination 30mons early. Very easy to work with and efficient

The plane is bare bones. You won’t have the new updates like phone chargers, personal screens, or WiFi

JFK
MEX
Excellent 10.0

Took off earlier than expected. Great snacks and drinks. Staff and flight attendants were very courteous and attentive. Great price on tickets as well.

OAX
MEX
Excellent 10.0

Staff was great, from check in to boarding and flight. First time flying Interjet and was pleasantly surprised. Every one was helpful and pleasant. On time. Did not expect beverage service on such a short flight.

Carry on Weight was to low. Luggage understandable but not personal handbag

BJX
MEX
Excellent 9.3

Clean, timely flight.

Connecting flight cancelled due to flight departure changes with initial flight. Cancellation policy is outrageous. Spent 3 hours making phone calls and super long hold times and spent time going around in circles.

JFK
MEX
Good 6.0

Increíble que no se pueda hacer en vuelos internacionales ni a través de la app

Sun, Jan 21
ORD
SJO
11h 40m
Tue, Jan 30
SJO
ORD
10h 10m
Trip: 10 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Nov 24
ORD
SJO
30h 38m
Tue, Dec 5
SJO
ORD
21h 57m
Trip: 12 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
BWI
Mediocre 2.0

Liked the price hated everthiig else

Price

IAH
LAS
Mediocre 3.0

Nothing to like really. Crew gathered in galley area, eating & drinking. Crew did not attend to passengers who were swinging feet & legs out in the aisle, pick up trash or other.

See above.///////////////////////////////////////////

LGA
FLL
Okay 4.6

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

DEN
LAS
Okay 5.0

Baggage policy should be more clearly advertised on the site. I could have booked a more expensive flight with a carry on included for less than what Spirit charges for flight and $50 for carry on.

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.

Wed, Feb 21
ORD
SJO
21h 55m
Fri, Mar 2
SJO
ORD
29h 15m
Trip: 10 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1140 reviews
Overall
7.6
Boarding
7.6
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
LAS
MTY
Excellent 10.0

Everything

?

GDL
MEX
Excellent 9.3

Flight delayed

OAX
MEX
Excellent 10.0

Staff was great, from check in to boarding and flight. First time flying Interjet and was pleasantly surprised. Every one was helpful and pleasant. On time. Did not expect beverage service on such a short flight.

Carry on Weight was to low. Luggage understandable but not personal handbag

LAX
MEX
Excellent 8.3

Great experience! We checked in quickly and the they boRded is all on time and also took off on time. The cherry on top was the fact we got to our destination 30mons early. Very easy to work with and efficient

The plane is bare bones. You won’t have the new updates like phone chargers, personal screens, or WiFi

BJX
MEX
Excellent 9.3

Clean, timely flight.

Connecting flight cancelled due to flight departure changes with initial flight. Cancellation policy is outrageous. Spent 3 hours making phone calls and super long hold times and spent time going around in circles.

Tue, Jan 23
ORD
SJO
11h 40m
Tue, Jan 30
SJO
ORD
8h 51m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Feb 7
ORD
SJO
19h 47m
Sun, Feb 11
SJO
ORD
34h 10m
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
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
CLE
Excellent 10.0

zero problems

all great

LGA
FLL
Okay 4.6

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

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.

FLL
ATL
Good 7.0

The landing was excellent

All the extra fees

Wed, Feb 28
ORD
SJO
21h 55m
Sat, Mar 10
SJO
ORD
17h 20m
Trip: 11 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1140 reviews
Overall
7.6
Boarding
7.6
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
MEX
PVR
Mediocre 2.0

None

Everything. Airline changed departure times on both flights. 50 minutes between connect flights. No other option but to cancel flight from Mexico City to Puerto Vallarta. Had to book a flight with another airline for an additional $300. Cancellation policy is terrible. Not my fault and had no other option.

JFK
MEX
Good 6.0

Increíble que no se pueda hacer en vuelos internacionales ni a través de la app

MEX
SAT
Mediocre 2.6

The check in is very Solw. They have to prepare the personnel

JFK
MEX
Excellent 10.0

Took off earlier than expected. Great snacks and drinks. Staff and flight attendants were very courteous and attentive. Great price on tickets as well.

GDL
MEX
Excellent 9.3

Flight delayed

Mon, Jan 29
ORD
SJO
11h 40m
Fri, Feb 2
SJO
ORD
8h 51m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Feb 5
ORD
SJO
7h 37m
Fri, Feb 9
SJO
ORD
9h 04m
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
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.

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

FLL
ATL
Good 7.0

The landing was excellent

All the extra fees

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.

Fri, Mar 2
ORD
SJO
13h 35m
Sun, Mar 11
SJO
ORD
20h 10m
Trip: 10 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1140 reviews
Overall
7.6
Boarding
7.6
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
MEX
JFK
Excellent 8.0

Pay for ny luggage

MEX
JFK
Mediocre 3.3

No entertainment they charged me double to change my departure, I had made an error on date.

JFK
MEX
Good 6.0

Increíble que no se pueda hacer en vuelos internacionales ni a través de la app

MEX
SAT
Mediocre 2.6

The check in is very Solw. They have to prepare the personnel

GDL
MEX
Excellent 9.3

Flight delayed

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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.