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

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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
12%
expected price increase
Average Price:
$415
(avg. price over the last 2 weeks)
Good Deal:
$336
or less (round trip)

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

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 $335 or less.
The cheapest flight from San Jose Juan Santamaria Intl to Chicago was found 59 days before departure, on average.
Book at least 2 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 3% more expensive 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 San Jose Juan Santamaria Intl to Chicago Flights

How long does a flight from San Jose Juan Santamaria Intl to Chicago take?
An average nonstop flight takes 7h 23m, covering a distance of 2213 miles.
How many flights are there between San Jose Juan Santamaria Intl and Chicago?
There are 5 (nonstop) flights between San Jose Juan Santamaria Intl and Chicago per week, averaging 0 per day.
Which airlines provide the cheapest flights from San Jose Juan Santamaria Intl to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Spirit Airlines ($316), Interjet ($338) and Multiple Airlines ($365).
Do I need a passport to fly between San Jose Juan Santamaria Intl and Chicago?
Yes.
Which airlines fly most frequently between San Jose Juan Santamaria Intl and Chicago?
United (0 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly San Jose Juan Santamaria Intl to Chicago?
For San Jose Juan Santamaria Intl to Chicago, Tuesday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Chicago back to San Jose Juan Santamaria Intl, the best deals are generally found on Tuesday, with Sunday being the most expensive.

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

Airports
Origin
San Jose
$316
only
$316
Destination
Chicago
$316
only
$316
$416
only
$416
Tue, May 1
SJO
ORD
10h 21m
Tue, May 8
ORD
SJO
8h 48m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52901 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LAX
ORD
Good 7.6

Great last minute price for trip to Chicago

Seats were a bit uncomfortable

PHX
MSP
Mediocre 2.0

Nothing

We arrived at the airport 2 hours before flight time, got ready to check our bag only to be told our flight to Phoenix had been cancelled and there was no replacement flight available until Friday - this was on Monday. No assistance to get us on another airline, just no customer service. We found another flight which cost double our fare and waited 12 hours in the airport— they didn’t even offer to buy us breakfast.

LGA
DTW
Good 6.0

Not a fan of spirit airlines. I would have rather paid an extra few dollars on flight cost for free water then have to be bothered paying on plane

ORD
LAX
Mediocre 2.0

Having to move from gate-to-gate three different times.

IAH
LAX
Mediocre 2.0

I tried to find out who checked me into the flight and her supervisor. I was discriminated against for having a service animal. I was told my doctors paperwork was insufficient. I called spirit airlines to see who was working and they could not find out. I will never fly again with spirit.

Wed, Apr 18
SJO
ORD
16h 25m
Sat, Apr 21
ORD
SJO
25h 30m
Trip: 4 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1455 reviews
Overall
7.6
Boarding
7.7
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
GDL
LAX
Excellent 8.0

The Aircraft was super clean and new looking. I was able to sleep n this flight.

LAX
CUN
Excellent 8.0

The flight was on time coming and going, also free snacks!

JFK
MEX
Excellent 10.0

They give you free food and drinks (alcoholic and not). Their seats are roomy and the staff is very nice

IAH
MTY
Good 7.6

Flight was short

Flight's departure time was delayed by an hour an 10 mins. Apparently, due to a long plane queue for take off

JFK
CUN
Excellent 8.6

Normal food and tv - no WiFi

Wed, Mar 7
SJO
ORD
10h 10m
Tue, Mar 20
ORD
SJO
7h 37m
Trip: 13 days
Overall 0.0 Poor
Based on 0 reviews
Tue, May 22
SJO
MDW
9h 17m
Wed, May 30
MDW
SJO
6h 46m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

SLC
YYZ
Excellent 9.6

Z

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

Sat, Feb 24
SJO
ORD
24h 54m
Sat, Mar 3
ORD
SJO
5h 15m
Trip: 8 days
9.9ExcellentShow reviews
Overall 9.9 Excellent
Based on 3 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
IAD
MUC
Excellent 9.3

United was flexible when I had to change my reservation at the last minute. Good service on board.

LAX
ORD
Good 7.0

Crew was nice

Plane was delayed for 4 hours, should have given us miles or a voucher

MUC
IAD
Excellent 9.6

Flexibility in changing reservation at the last minute. Excellent service on board, good food.

EWR
TPA
Excellent 8.0

Made up time for delayed departure

So cramped. Sat next to very obese person....spilled onto my seat

IAD
NRT
Excellent 10.0

For a little over $2000 you get an economy seat non-stop from DC to Tokyo and back. Meals were good. As economy seats go, it's comfortable. Midweek the flight is about half to two thirds full. So you might be able to stretch out even!

Tue, Jul 10
SJO
MDW
15h 47m
Mon, Jul 16
MDW
SJO
12h 45m
Trip: 7 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 5565 reviews
Overall
7.4
Boarding
7.4
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
LAX
GDL
Excellent 9.6

How they offered food and snacks and drinks crew was friendly

Boarding took a bit long but other than that everything was perfect

DEN
MEX
Excellent 8.3

i have a 15 hour layover and was told i would need to collect my bag, but in mexico city they just said it would beon the next flight. praying it is.

MEX
JFK
Excellent 10.0

Helpful check-in in Mexico City.

CUN
MEX
Excellent 8.0

The crew

The front desk staff

MEX
CUN
Mediocre 2.0

Nothing!!!!

A horrible flight!!! We arrived at 5:04pm then we sat on the tamarac for 40 minutes before they could find a gate for us!!!! What a horrible lack of management!’ Who runs this airport/airline!? At the end they moved us to completly different terminal!!! Had to find a new transportation to the hotel!!! Again, what a horrible display of management skills!!

Tue, Jul 31
SJO
ORD
8h 32m
Wed, Aug 8
ORD
SJO
7h 20m
Trip: 9 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52901 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
LAX
Mediocre 2.0

Having to move from gate-to-gate three different times.

EWR
IAH
Excellent 8.0

Spirit has gotten better with their customer service. Via email, not by phone.

The flight options need to better

MYR
PHL
Excellent 10.0

flight attendants, price, easy of checking in

bag fees

TPA
MSY
Excellent 10.0

I read that everything was ala carte on Spirit Airlines, so I knew to pay for my bag online and carry on only the size allowed for free. The boarding and flight was very smooth. There are kiosks at the airport to print your boarding pass which also saves you money.

I didn't understand how to pay for a beverage/snack while on board the plane. Wish that something that inexpensive would be offered without charge!

DEN
ORD
Excellent 8.0

Good thing I travel light! I thought the round trip fare was great!

Seating was cramped and seat back did not move

Thu, Mar 8
SJO
ORD
17h 20m
Mon, Mar 19
ORD
SJO
23h 40m
Trip: 11 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1455 reviews
Overall
7.6
Boarding
7.7
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
JFK
CUN
Excellent 8.6

Normal food and tv - no WiFi

JFK
MEX
Excellent 10.0

They give you free food and drinks (alcoholic and not). Their seats are roomy and the staff is very nice

CUN
LAX
Excellent 9.6

I liked that everything went smooth on the flight. Loved the leg room!!

There was no Wi-Fi. On this flight i was not able to plug my ear phones to armrest.

MID
MEX
Excellent 10.0

Roominess of seats.

LAX
MEX
Good 6.6

The efficiency

Wed, Aug 22
SJO
ORD
10h 24m
Wed, Aug 29
ORD
SJO
7h 20m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52901 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LGA
DTW
Good 6.0

Not a fan of spirit airlines. I would have rather paid an extra few dollars on flight cost for free water then have to be bothered paying on plane

MYR
PHL
Excellent 10.0

flight attendants, price, easy of checking in

bag fees

PHX
MSP
Mediocre 2.0

Nothing

We arrived at the airport 2 hours before flight time, got ready to check our bag only to be told our flight to Phoenix had been cancelled and there was no replacement flight available until Friday - this was on Monday. No assistance to get us on another airline, just no customer service. We found another flight which cost double our fare and waited 12 hours in the airport— they didn’t even offer to buy us breakfast.

ORD
LAX
Mediocre 2.0

Having to move from gate-to-gate three different times.

DEN
ORD
Excellent 8.0

Good thing I travel light! I thought the round trip fare was great!

Seating was cramped and seat back did not move

Mon, Jul 23
SJO
MDW
8h 55m
Tue, Jul 31
MDW
SJO
8h 00m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

Tue, May 22
SJO
ORD
10h 21m
Tue, May 29
ORD
SJO
8h 48m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52901 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
MYR
PHL
Excellent 10.0

flight attendants, price, easy of checking in

bag fees

TPA
MSY
Excellent 10.0

I read that everything was ala carte on Spirit Airlines, so I knew to pay for my bag online and carry on only the size allowed for free. The boarding and flight was very smooth. There are kiosks at the airport to print your boarding pass which also saves you money.

I didn't understand how to pay for a beverage/snack while on board the plane. Wish that something that inexpensive would be offered without charge!

PHX
MSP
Mediocre 2.0

Nothing

We arrived at the airport 2 hours before flight time, got ready to check our bag only to be told our flight to Phoenix had been cancelled and there was no replacement flight available until Friday - this was on Monday. No assistance to get us on another airline, just no customer service. We found another flight which cost double our fare and waited 12 hours in the airport— they didn’t even offer to buy us breakfast.

PHL
FLL
Mediocre 2.0

Over 2 hrs late. No explanation.

ORD
LAX
Mediocre 2.0

Having to move from gate-to-gate three different times.

Fri, Jun 1
SJO
ORD
10h 21m
Tue, Jun 5
ORD
SJO
7h 23m
Trip: 5 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52901 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PHL
FLL
Mediocre 2.0

Over 2 hrs late. No explanation.

LGA
DTW
Good 6.0

Not a fan of spirit airlines. I would have rather paid an extra few dollars on flight cost for free water then have to be bothered paying on plane

TPA
MSY
Excellent 10.0

I read that everything was ala carte on Spirit Airlines, so I knew to pay for my bag online and carry on only the size allowed for free. The boarding and flight was very smooth. There are kiosks at the airport to print your boarding pass which also saves you money.

I didn't understand how to pay for a beverage/snack while on board the plane. Wish that something that inexpensive would be offered without charge!

IAH
TPA
Okay 4.3

Price Get what you pay

Late flight Indifferent flight attendants

PHX
MSP
Mediocre 2.0

Nothing

We arrived at the airport 2 hours before flight time, got ready to check our bag only to be told our flight to Phoenix had been cancelled and there was no replacement flight available until Friday - this was on Monday. No assistance to get us on another airline, just no customer service. We found another flight which cost double our fare and waited 12 hours in the airport— they didn’t even offer to buy us breakfast.

Wed, Mar 21
SJO
MDW
14h 45m
Wed, Apr 4
MDW
SJO
8h 46m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

Tue, Jun 26
SJO
ORD
16h 25m
Sun, Jul 8
ORD
SJO
9h 55m
Trip: 13 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1455 reviews
Overall
7.6
Boarding
7.7
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
CUN
LAX
Excellent 9.6

I liked that everything went smooth on the flight. Loved the leg room!!

There was no Wi-Fi. On this flight i was not able to plug my ear phones to armrest.

LAX
MEX
Good 6.6

The efficiency

LAX
CUN
Excellent 8.0

The flight was on time coming and going, also free snacks!

JFK
MEX
Good 6.6

Good price, free food and drink, decent leg room

Seats were just okay, definitely not plush, no entertainment.

MID
MEX
Excellent 10.0

Roominess of seats.

Wed, Aug 1
SJO
MDW
8h 55m
Mon, Aug 6
MDW
SJO
8h 00m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

JFK
CDG
Excellent 10.0

The food and the service

Sun, Jul 1
SJO
ORD
20h 10m
Thu, Jul 5
ORD
SJO
23h 35m
Trip: 5 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 1455 reviews
Overall
7.6
Boarding
7.7
Comfort
7.9
Crew
8.0
Entertainment
6.4
Food
6.9
JFK
CUN
Excellent 8.6

Normal food and tv - no WiFi

LAX
MEX
Good 6.6

The efficiency

JFK
MEX
Good 6.6

Good price, free food and drink, decent leg room

Seats were just okay, definitely not plush, no entertainment.

IAH
MTY
Good 7.6

Flight was short

Flight's departure time was delayed by an hour an 10 mins. Apparently, due to a long plane queue for take off

MID
MEX
Excellent 10.0

Roominess of seats.

Wed, Apr 18
SJO
MDW
8h 20m
Sat, Apr 21
MDW
SJO
8h 46m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

SLC
YYZ
Excellent 9.6

Z

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

Tue, Jul 10
SJO
ORD
7h 23m
Mon, Jul 16
ORD
SJO
29h 00m
Trip: 7 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52901 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
IAH
LAX
Mediocre 2.0

I tried to find out who checked me into the flight and her supervisor. I was discriminated against for having a service animal. I was told my doctors paperwork was insufficient. I called spirit airlines to see who was working and they could not find out. I will never fly again with spirit.

ORD
LAX
Mediocre 2.0

Having to move from gate-to-gate three different times.

EWR
LAS
Mediocre 2.0

seats were comfortable from vegas to lax...

the fee increase to chevk bag at airpirt is ridiculous:( Majes me not want to fly spirit again sadly..... not necessary

PHX
MSP
Mediocre 2.0

Nothing

We arrived at the airport 2 hours before flight time, got ready to check our bag only to be told our flight to Phoenix had been cancelled and there was no replacement flight available until Friday - this was on Monday. No assistance to get us on another airline, just no customer service. We found another flight which cost double our fare and waited 12 hours in the airport— they didn’t even offer to buy us breakfast.

DEN
ORD
Excellent 8.0

Good thing I travel light! I thought the round trip fare was great!

Seating was cramped and seat back did not move

Tue, Jun 26
SJO
MDW
14h 50m
Tue, Jul 10
MDW
SJO
20h 46m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

Wed, Jul 18
SJO
MDW
8h 55m
Sun, Jul 22
MDW
SJO
14h 40m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
YYZ
Excellent 9.6

Z

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

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San Jose Juan Santamaria Intl to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from San Jose Juan Santamaria Intl
Flight Price $316
Distance 2213 miles
Airlines Spirit Airlines, Interjet, Delta, United, Aeromexico
*
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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.