Cheap Flight Tickets from Chicago (ORD) to San Jose (SJO), Starting at $1309

Good to Know: Cheapest and Fastest ORD - SJO Flights

Useful information for finding best airline tickets from Chicago O'Hare International to Juan Santamaria International on your next trip.

Cheapest Round Trip Flight

$1309

AV Avianca • 1 stop • 29h 10m

Dec 24 – Jan 03

The cheapest round trip flight from Chicago to San Jose (ORD-SJO-ORD) is currently $1309

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Cheapest Direct Flight

$2357

UA United Airlines • nonstop • 8h 33m

Dec 24

The cheapest nonstop flight from Chicago to San Jose (ORD-SJO) is currently $2357

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Fastest Flight

8h 33m

The fastest nonstop flight from Chicago to San Jose (ORD-SJO) takes 8h 33m

Top Airlines Flying from Chicago to San Jose

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Avianca Airline - AV

Avianca

Air Canada-AC

Air Canada

Copa Airlines (CM)

Copa Airlines

Latest Flight Deals from Chicago (ORD) to San Jose (SJO)

Compare and book low fare round-trip air tickets from Chicago to San Jose. Ideal for travelers with confirmed return itineraries.

Dec 24 - Jan 03, Economy
AV
Chicago → San Jose
29h 10m
10:30 PM - 4:20 PM • 1 stop
AV
Chicago → San Jose
44h 15m
10:00 AM - 12:55 PM • 1 stop
$1309
Avianca
Dec 24 - Jan 03, Economy
AC
Chicago → San Jose
36h 53m
10:05 AM - 8:18 AM • 2 stops
AV
Chicago → San Jose
12h
5:35 AM - 12:55 PM • 1 stop
$1551
Air Canada
Dec 24 - Jan 03, Economy
F9
Chicago → San Jose
24h 12m
7:00 AM - 9:52 PM • 2 stops
Y4
Chicago → San Jose
25h 27m
1:16 PM - 4:43 AM • 2 stops
$1733
Frontier Airlines
Dec 24 - Jan 03, Economy
AA
Chicago → San Jose
15h 35m
5:00 AM - 2:35 PM • 1 stop
AA
Chicago → San Jose
18h 57m
6:22 AM - 5:59 PM • 1 stop
$1992
American Airlines
Dec 24 - Jan 03, Economy
AA
Chicago → San Jose
15h 17m
1:44 PM - 11:01 PM • 1 stop
AA
Chicago → San Jose
18h 57m
6:22 AM - 5:59 PM • 1 stop
$1992
American Airlines
Dec 24 - Jan 03, Economy
AC
Chicago → San Jose
25h 36m
6:54 AM - 10:30 PM • 1 stop
AC
Chicago → San Jose
18h 33m
8:45 AM - 7:58 PM • 1 stop
$2914
Air Canada

Fly from Chicago to San Jose with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to San Jose? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to San Jose Flights

What are the airports in Chicago?
MDW,ORD
What’s the most popular airline flying from ORD to SJO?
The most popular airline flying from Chicago to San Jose are
Can I fly from ORD to SJO non-stop?
Yes, you can fly ORD to SJO non-stop on
Which airlines fly nonstop between Chicago and San Jose?
The non-stop flights between Chicago and San Jose are .
What’s the earliest departure time from ORD to SJO Airport?
The earliest flight leaves ORD at 5:00 am and lands in SJO - Juan Santamaria International
What are the airports in San Jose?
SJO
Can I make changes to my Chicago to San Jose flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from ORD to SJO?
Read the fare rules of the Chicago to San Jose air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and San Jose?
operate flights between Chicago and San Jose
How long does a flight from Chicago to San Jose take?
It takes approximately 5 hour to fly non-stop from ORD to SJO, which is 2213.63 miles by air.
Which airlines provide the cheapest flights from Chicago (ORD) to San Jose (SJO) ?
In the past couple of days, the cheapest tickets to SJO from ORD were found on F9 : USD 1733
Do I need a passport to fly between ORD and SJO?
Yes
What’s the latest departure time from ORD to SJO ?
The last flight leaves ORD at 10:30 pm

Chicago (ORD) to San Jose (SJO): Airport Information

Origin Airport Chicago O'Hare International , Chicago, US
Destination Airport Juan Santamaria International , San Jose, CR
Distance 2214 miles

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