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 41 days to departure.
Normally the best deals on Chicago to San Jose flights are available 2 to 4 months prior to departure.
Days before departure
Best month
Cheapest time of year to fly to San Jose from Chicago is January and February. Most expensive are November and December.
The cheapest flights from Chicago to San Jose are currently available between June and July.
Impact on price
Cheapest airline
According to our data, Spirit Airlines, Avianca El Salvador and Major US Carrier are the cheapest airlines to fly this route.
Spirit Airlines, Avianca El Salvador and Major US Carrier are the most popular choices flying from Chicago to San Jose.
Impact on price (additional fees may apply)
Spirit Airlines
+2%
Avianca El Salvador
+5%
Major US Carrier
+14%
American Airlines
+17%
Volaris
+23%
United Airlines
+24%
Best time to fly
Chicago to San Jose flights are approximately 3% more expensive in the morning than in the evening.
Morning flights tend to be the most expensive.
Impact on price
Cheapest day
Saturday is normally the most expensive day to fly, whilst Wednesday tends to be the cheapest.
Cheapest day of week is typically Wednesday and the most expensive is typically Saturday.
Impact on price
Cheapest route
Fly O'Hare Intl - Juan Santamaria for the best Chicago to San Jose flight prices saving up to 0% on average.
O'Hare Intl - Juan Santamaria tends to be 0% cheaper than Midway - Juan Santamaria.
momondo compares flights to San Jose from Chicago from 25 different sites.
Impact on price
O'Hare Intl-Juan Santamaria
+0%
Midway-Juan Santamaria
+2%
Direct flights
There are direct flights from Chicago to Juan Santamaria all week with a flight time of 5 hours 15 minutes.
Direct flights available: 9 PER WEEK
Popular non-direct routes for this connection are O'Hare Intl - Hartsfield Jackson - Juan Santamaria, O'Hare Intl - Juarez Intl - Juan Santamaria and O'Hare Intl - Dallas Ft Worth - Comalapa Intl. - Juan Santamaria.
You can fly from Chicago to Juan Santamaria indirect via Hartsfield Jackson, Juarez Intl or Dallas Ft Worth.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Go right away

Last minute flights from Chicago to San Jose
Return trip
27 Apr - 4 May
404 CAD
JustFly
CHI CHI
29h 7min
1 stop
SJO SJO
SJO SJO
7h 21min
1 stop
CHI CHI

Go for less - experience more

Cheap flights from Chicago to San Jose
Return trip
15 Apr - 22 Apr
395 CAD
AirticketsCA
CHI CHI
5h 15min
Direct
SJO SJO
SJO SJO
16h 42min
1 stop
CHI CHI
Return trip
27 Apr - 4 May
404 CAD
JustFly
CHI CHI
29h 7min
1 stop
SJO SJO
SJO SJO
7h 21min
1 stop
CHI CHI
Return trip
17 Apr - 24 Apr
501 CAD
FaregeekCA
CHI CHI
25h 32min
1 stop
SJO SJO
SJO SJO
8h 44min
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
41%
San Jose
3.09 CAD
Cappuccino is 41% cheaper in San Jose than Chicago
MEAL
Inexpensive
Chicago
20.05 CAD
52%
San Jose
9.62 CAD
Meal is 52% cheaper in San Jose than Chicago
MILK
1 liter
Chicago
3.88 CAD
-83%
San Jose
7.09 CAD
Milk is 83% more expensive in San Jose than Chicago
BUS
One-way ticket
Chicago
3.01 CAD
68%
San Jose
0.96 CAD
Bus is 68% cheaper in San Jose than Chicago
MOVIE THEATER
1 ticket
Chicago
16.04 CAD
48%
San Jose
8.41 CAD
movie theater is 48% cheaper in San Jose than Chicago
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