Cheap Flights from San Jose to Chicago
Cheap Flights from San Jose to Chicago
Looking for cheap flights from San Jose to Chicago? 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 San Jose to Chicago vary by season, cabin, and date, but available award flights can start around 12,500–17,500 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 San Jose to Chicago for specific travel dates.
2026-11-05
SJO - ORD
Economy | 1 Stop | 9+ left
From 12,500 Pts + $139.3
2026-11-05
SJO - ORD
Economy | 1 Stop | 9+ left
From 15,000 Pts + $117.4
2027-01-01
SJO - ORD
Economy | 1 Stop | 4 left
From 15,000 Pts + $117.4
2026-11-05
SJO - ORD
Economy | 1 Stop
From 16,500 Pts + $73.4
2026-11-05
SJO - ORD
Economy | 1 Stop | 9+ left
From 17,500 Pts + $93.4
2026-11-06
SJO - ORD
Economy | 1 Stop | 9+ left
From 17,500 Pts + $93.4
San Jose to Chicago 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
Chicago is in the same time zone as San Jose.
Airports in San Jose
SJO · Juan Santamaria Intl
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights San Jose - Milwaukee · Milwaukee is 73 mi from Chicago
Flights Liberia - Chicago · Liberia is 100 mi from San Jose
Premium cabin flights from San Jose to Chicago
Premium cabin
2026-11-06
SJO - ORD
First | 1 Stop | 7 left
From 90,000 Pts + $73.4
Premium cabin
2026-11-06
SJO - MDW
First | 1 Stop | 1 left
From 90,000 Pts + $73.4
Premium cabin
2026-11-08
SJO - ORD
First | 1 Stop | 2 left
From 90,000 Pts + $73.4
Premium cabin
2026-11-08
SJO - MDW
First | 1 Stop | 1 left
From 90,000 Pts + $73.4
Premium cabin
2026-11-05
SJO - ORD
First | 2 Stops | 1 left
From 90,000 Pts + $79
Premium cabin
2026-11-07
SJO - MDW
First | 1 Stop | 4 left
From 100,000 Pts + $73.4
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
Frequently Asked Questions
The cheapest route from San Jose to Chicago 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 San Jose to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from San Jose to Chicago.
San Jose and Chicago 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.
Chicago is in the same time zone as San Jose.
Departures from San Jose: Juan Santamaria Intl (SJO). Arrivals in Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD).
Travelers searching this route also look at other popular routes into Chicago, plus the return trip when we track it. Fares and award space change daily.
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