Flights from Chicago to San Jose

Search and find cheap flights from Chicago to San Jose (Costa Rica, North America)
Search and find cheap flights from Chicago to San Jose (Costa Rica, North America)

Looking for the best tickets for Chicago to San Jose?

Look no more. We’ve gone through the latest 1,010,616 fares to bring you all the insights you could possibly want.
Best time to book
Cheapest time to buy a ticket for Chicago — San Jose is approximately 49 days to departure.
Chicago to San Jose flights are usually cheapest between 2 and 4 months before departure.
Days before departure
Best month
Cheapest time of year to fly to San Jose from Chicago is March and April. Most expensive are November and December.
The cheapest flights from Chicago to San Jose are currently available between August and September.
Impact on price
Cheapest airline
According to our data, Spirit Airlines, Major US Carrier and Volaris are the cheapest airlines to fly this route.
Spirit Airlines, Major US Carrier and Volaris are the most popular choices flying from Chicago to San Jose.
Impact on price (additional fees may apply)
Spirit Airlines
+19%
Major US Carrier
+20%
Volaris
+27%
United Airlines
+32%
Interjet
+33%
Delta Air Lines
+35%
Best time to fly
Chicago to San Jose flights are approximately 4% more expensive in the noon than in the evening.
Noon flights tend to be the most expensive.
Impact on price
Cheapest day
Friday is normally the most expensive day to fly, whilst Tuesday tends to be the cheapest.
Cheapest day of week is typically Tuesday and the most expensive is typically Friday.
Impact on price
Cheapest route
Fly Midway - Juan Santamaria for the best Chicago to San Jose flight prices saving up to 0% on average.
Midway - Juan Santamaria tends to be 0% cheaper than O'Hare Intl - Juan Santamaria.
momondo compares flights to San Jose from Chicago from 25 different sites.
Impact on price
Midway-Juan Santamaria
+0%
O'Hare Intl-Juan Santamaria
+0%
Direct flights
There are direct flights from Chicago to Juan Santamaria on Thursdays, Fridays, Saturdays with a flight time of 5 hours 15 minutes.
Direct flights available: 4 PER WEEK
Popular non-direct routes for this connection are O'Hare Intl - Comalapa Intl. - Juan Santamaria, O'Hare Intl - Tocumen Intl - Juan Santamaria and O'Hare Intl - Hartsfield Jackson - Juan Santamaria.
You can fly from Chicago to Juan Santamaria indirect via Comalapa Intl., Tocumen Intl or Hartsfield Jackson.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Go right away

Last minute flights from Chicago to San Jose
Return trip
2 Sep - 12 Sep
466 CAD
MytripCA
CHI CHI
21h 15min
2 stops
SJO SJO
SJO SJO
23h 6min
2 stops
CHI CHI
Return trip
11 Aug - 21 Aug
481 CAD
Orbitz
CHI CHI
17h 17min
1 stop
SJO SJO
SJO SJO
39h 13min
2 stops
CHI CHI

Go for less - experience more

Cheap flights from Chicago to San Jose
Return trip
17 Jun - 24 Jun
555 CAD
AirticketsCA
CHI CHI
12h 10min
1 stop
SJO SJO
SJO SJO
22h 16min
1 stop
CHI CHI
Return trip
18 Jun - 24 Jun
567 CAD
KissAndFlyUS
CHI CHI
23h 40min
1 stop
SJO SJO
SJO SJO
19h 55min
1 stop
CHI CHI
Return trip
17 Jun - 23 Jun
568 CAD
FlyFar
CHI CHI
8h 33min
1 stop
SJO SJO
SJO SJO
7h 23min
1 stop
CHI CHI

Weather forecast for San Jose

Going soon? Be prepared for the weather in San Jose.

So what's it going to cost once you're in San Jose

Compare the costs of everyday items in Chicago and San Jose
CAPPUCCINO
Regular
Chicago
5.29 CAD
42%
San Jose
3.05 CAD
Cappuccino is 42% cheaper in San Jose than Chicago
MEAL
Inexpensive
Chicago
20.25 CAD
54%
San Jose
9.29 CAD
Meal is 54% cheaper in San Jose than Chicago
MILK
1 liter
Chicago
4.03 CAD
-74%
San Jose
7.01 CAD
Milk is 74% more expensive in San Jose than Chicago
BUS
One-way ticket
Chicago
3.37 CAD
72%
San Jose
0.93 CAD
Bus is 72% cheaper in San Jose than Chicago
MOVIE THEATER
1 ticket
Chicago
16.19 CAD
50%
San Jose
8.13 CAD
movie theater is 50% cheaper in San Jose than Chicago
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