Lowest Prices
Uncover the best deals on Chicago to San Jose flights by comparing fares from hundreds of airlines and agencies.
Good to Know: Cheapest and Fastest CHI - SJO Flights
Useful information for finding best airline tickets from Chicago All Airport to Juan Santamaria International on your next trip.
Cheapest Round Trip Flight
$319
Southwest Airlines
• 1 stop
• 24h 10m
Dec 10 – Dec 17
The cheapest round trip flight from Chicago to San Jose (CHI-SJO-CHI) is currently $319
Fastest Flight
10h 31m
The fastest nonstop flight from Chicago to San Jose (CHI-SJO) takes 10h 31m
Top Airlines Flying from Chicago to San Jose
Latest Flight Deals from Chicago (CHI) 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 10 - Dec 17, Economy
Chicago → San Jose
24h 10m
4:10 PM - 7:00 AM • 1 stop
Chicago → San Jose
28h 45m
2:10 PM - 7:35 AM • 1 stop
Southwest Airlines
Dec 11 - Dec 18, Economy
Chicago → San Jose
12h 16m
9:00 AM - 7:53 PM • 1 stop
Chicago → San Jose
8h 52m
1:25 PM - 6:57 PM • nonstop
United Airlines
Dec 11 - Dec 18, Economy
Chicago → San Jose
10h 31m
9:00 AM - 1:05 PM • 1 stop
Chicago → San Jose
11h 49m
3:08 PM - 11:59 PM • 1 stop
American Airlines
Dec 10 - Dec 17, Economy
Chicago → San Jose
38h 32m
9:27 PM - 8:39 PM • 1 stop
Chicago → San Jose
8h 52m
1:25 PM - 6:57 PM • nonstop
United Airlines
Dec 11 - Dec 18, Economy
Chicago → San Jose
39h 4m
9:21 PM - 9:05 PM • 3 stops
Chicago → San Jose
33h 55m
2:25 AM - 11:00 PM • 1 stop
Frontier Airlines
FAQs on Chicago to San Jose Flights
What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from CHI to SJO?
The most popular airline flying from Chicago to San Jose are
Can I fly from CHI to SJO non-stop?
NO
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 CHI to SJO Airport?
The earliest flight leaves CHI at 9:00 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 CHI 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 CHI to SJO, which is 2213.63 miles by air.
Which airlines provide the cheapest flights from Chicago (CHI) to San Jose (SJO) ?
In the past couple of days, the cheapest tickets to SJO from CHI were found on WN : USD 319
Do I need a passport to fly between CHI and SJO?
Yes
What’s the latest departure time from CHI to SJO ?
The last flight leaves CHI at 9:27 pm
Chicago (CHI) to San Jose (SJO): Airport Information
| Origin Airport | Chicago All Airport, Chicago, US |
| Destination Airport | Juan Santamaria International , San Jose, CR |
| Distance | 2214 miles |
More Flight Options for Chicago (CHI) and San Jose (SJO)
Flights from Chicago (ORD)
to Las Vegas (LAS)
Flights from Chicago (ORD)
to Los Angeles (LAX)
Flights from Chicago (ORD)
to Charlotte (CLT)
Flights from Chicago (ORD)
to Washington (IAD)
Flights from Chicago (ORD)
to Orlando (MCO)
Flights from Chicago (ORD)
to Fort Lauderdale (FLL)
Flights from Chicago (ORD)
to Tampa (TPA)
Flights from Chicago (ORD)
to Atlanta (ATL)
Flights from Chicago (ORD)
to Miami (MIA)
Flights from Chicago (MDW)
to Raleigh/Durham (RDU)
Flights from Chicago (ORD)
to Dublin (DUB)
Flights from Chicago (MDW)
to Washington (DCA)
Flights from Chicago (MDW)
to Las Vegas (LAS)
Flights from Chicago (ORD)
to Cancún (CUN)
Flights from Chicago (MDW)
to Orlando (MCO)
Flights from Chicago (MDW)
to Atlanta (ATL)
Flights from Chicago (ORD)
to Dallas (DFW)
Flights from Chicago (ORD)
to Dallas (DFW)
Flights from Chicago (MDW)
to San Juan (SJU)
Flights from Chicago (ORD)
to San Francisco (SFO)
Flights from Milwaukee (MKE)
to San Jose (SJO)
Flights from Oklahoma City (OKC)
to San Jose (SJO)
Flights from Orlando (MCO)
to San Jose (SJO)
Flights from Chicago (CHI)
to San Jose (SJO)
Flights from Dallas (DFW)
to San Jose (SJO)
Flights from Dallas (DFW)
to San Jose (SJO)
Flights from Miami (MIA)
to San Jose (SJO)
Flights from Austin (AUS)
to San Jose (SJO)
Flights from Guatemala City (GUA)
to San Jose (SJO)
Flights from Los Angeles (LAX)
to San Jose (SJO)
Flights from Montréal (YUL)
to San Jose (SJO)
Flights from Dallas (DAL)
to San Jose (SJO)
Flights from Baltimore (BWI)
to San Jose (SJO)
Flights from Baltimore (BWI)
to San Jose (SJO)
Flights from Houston (HOU)
to San Jose (SJO)
Flights from Buenos Aires (EZE)
to San Jose (SJO)
Flights from New York (LGA)
to San Jose (SJO)
Flights from Las Vegas (LAS)
to San Jose (SJO)
Flights from Charlotte (CLT)
to San Jose (SJO)
Flights from Fort Lauderdale (FLL)
to San Jose (SJO)
Cheap flights to North America (NA)
Cheap flights to United States (US)
Cheap flights to Costa Rica (CR)
Cheap flights from North America (NA)
Cheap flights from Costa Rica (CR)
Cheap flights from United States (US)
Flights to Chicago (MDW)
Flights to Chicago (ORD)
Flights to San Jose (SJO)
Flights from Chicago (MDW)
Flights from Chicago (ORD)
Flights from San Jose (SJO)
Flights from San Jose (SJO)
to Chicago (MDW)
Flights from San Jose (SJO)
to Chicago (ORD)
Why Fareleaders for CHI to SJO Plane Tickets
New Deals Everyday
Get the best prices on CHI to SJO flights—we update our fares daily so you never miss a saving.
No Service Fees
Compare hundreds of Chicago to San Jose flights and secure the best deals—we never add any service fees.