Cheap Flights from Chicago to San Jose
Cheap Flights from Chicago to San Jose
Looking for cheap flights from Chicago to San Jose? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to San Jose vary by season, cabin, and date, but available award flights can start around 10,000–12,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to San Jose for specific travel dates.
2026-11-28
ORD - SJO
Economy | 1 Stop
From 10,000 Pts + $24.7
2026-11-29
ORD - SJO
Economy | 1 Stop
From 10,000 Pts + $24.7
2026-12-29
ORD - SJO
Economy | 2 Stops
From 10,000 Pts + $30.3
2026-11-26
ORD - SJO
Economy | 1 Stop | 5 left
From 12,500 Pts + $95
2026-12-31
ORD - SJO
Economy | 1 Stop | 9+ left
From 12,500 Pts + $95
2026-12-31
ORD - SJO
Economy | 1 Stop | 9+ left
From 12,500 Pts + $95
Chicago to San Jose flight facts
Distance
2,216 mi
3,566 km in a straight line
Estimated flight time
about 5h
In the air, for the straight-line distance
Time difference
Same time zone
San Jose is in the same time zone as Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in San Jose
SJO · Juan Santamaria Intl
Nearby airport alternatives
Flights Milwaukee - San Jose · Milwaukee is 73 mi from Chicago
Flights Chicago - Liberia · Liberia is 100 mi from San Jose
Flights Grand Rapids - San Jose · Grand Rapids is 142 mi from Chicago
Premium cabin flights from Chicago to San Jose
Premium cabin
2026-11-07
ORD - SJO
First | 2 Stops
From 107,000 Pts + $24.7
Premium cabin
2026-11-07
ORD - SJO
First | 1 Stop | 2 left
From 107,400 Pts + $24.7
Premium cabin
2026-11-07
MDW - SJO
First | 1 Stop | 2 left
From 107,400 Pts + $24.7
Premium cabin
2026-11-09
ORD - SJO
First | 1 Stop | 3 left
From 107,400 Pts + $24.7
Premium cabin
2026-11-05
ORD - SJO
First | 2 Stops | 3 left
From 110,000 Pts + $24.7
Premium cabin
2026-11-06
ORD - SJO
First | 2 Stops | 3 left
From 110,000 Pts + $24.7
Selected hotels for your next stay
San jose (Costa Rica)
Alta Las Palomas(SLH)
From 60,000 Pts or $185
Monteverge (Costa Rica)
Senda Monteverde Hotel, an SLH Hotel
From 95,000 Pts or $504
Manuel Antonio (Costa Rica)
Los Altos Resort, an SLH Hotel
From 140,000 Pts or $719
Frequently Asked Questions
The cheapest route from Chicago to San Jose depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to San Jose.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to San Jose.
Chicago and San Jose are about 2,216 miles (3,566 km) apart in a straight line.
Flying the 2,216-mile straight-line distance takes about 5h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
San Jose is in the same time zone as Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in San Jose: Juan Santamaria Intl (SJO).
Travelers searching this route also look at other popular routes into San Jose, plus the return trip when we track it. Fares and award space change daily.
Our mission is to provide
the simplest and best
points travel planning
experience. Yeah!
Our mission is to provide the simplest and best
points travel planning experience. Yeah!
