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 and date, but economy flights can start around 12,500–23,500 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.
2026-04-16
SJO - ORD
Economy | 1 Stop | 1 left
From 20,000 Pts + $73.3
2026-04-16
SJO - ORD
Economy | 1 Stop
From 23,500 Pts + $73
2026-04-16
SJO - ORD
Economy | 1 Stop | 7 left
From 12,500 Pts + $143.8
2026-04-16
SJO - ORD
Economy | 1 Stop | 1 left
From 18,150 Pts + $121.4
2026-04-18
SJO - ORD
Economy | 1 Stop | 5 left
From 23,500 Pts + $200.8
2026-04-20
SJO - ORD
Economy | 1 Stop | 1 left
From 12,500 Pts + $139.6
Premium cabin flights from San Jose to Chicago
Premium cabin
2026-04-16
SJO - ORD
Business | 2 Stops | 4 left
From 38,500 Pts + $74.5
Premium cabin
2026-04-16
SJO - ORD
Business | 2 Stops
From 53,000 Pts + $204.2
Premium cabin
2026-04-16
SJO - ORD
Business | 2 Stops | 4 left
From 25,000 Pts + $145.1
Premium cabin
2026-04-16
SJO - ORD
Business | 1 Stop
From 34,000 Pts + $73
Premium cabin
2026-04-20
SJO - ORD
Business | 2 Stops | 2 left
From 38,500 Pts + $75.1
Premium cabin
2026-04-20
SJO - ORD
Business | 1 Stop | 2 left
From 25,000 Pts + $143.9
Selected hotels for your next stay
Vernon Hills (United States)
Hotel Indigo Chicago-Vernon Hills
From 16,000 Pts or $115
Chicago (United States)
Thompson Chicago
From 17,000 Pts or $218
Chicago (United States)
Park Hyatt Chicago
From 21,000 Pts or $502
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.
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