Cheap Flights from San Diego to Chicago
Looking for cheap flights from San Diego 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 Diego to Chicago vary by season and date, but economy flights can start around 12,500–20,700 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 Diego to Chicago for specific travel dates.
2026-04-30
SAN - ORD
Economy | Non stop | 9+ left
From 15,000 Pts + $5.6
2026-05-01
SAN - ORD
Economy | Non stop | 9+ left
From 15,000 Pts + $5.5
2026-05-01
SAN - ORD
Economy | Non stop | 9+ left
From 12,500 Pts + $18.1
2026-05-01
SAN - ORD
Economy | Non stop | 9+ left
From 15,000 Pts + $5.6
2026-05-01
SAN - ORD
Economy | Non stop
From 20,700 Pts + $5.6
2026-05-01
SAN - ORD
Economy | Non stop | 9+ left
From 17,880 Pts + $30.6
Premium cabin flights from San Diego to Chicago
Premium cabin
2026-05-01
SAN - ORD
First | Non stop | 9+ left
From 25,000 Pts + $18.1
Premium cabin
2026-05-01
SAN - ORD
First | Non stop
From 22,000 Pts + $5.6
Premium cabin
2026-05-02
SAN - ORD
Business | Non stop
From 43,600 Pts + $5.6
Premium cabin
2026-05-02
SAN - ORD
Business | Non stop | 7 left
From 40,000 Pts + $42.4
Premium cabin
2026-05-02
SAN - ORD
First | Non stop | 9+ left
From 25,000 Pts + $18.1
Premium cabin
2026-05-02
SAN - ORD
First | Non stop
From 20,000 Pts + $5.6
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 17,000 Pts or $322
Chicago (United States)
Thompson Chicago
From 17,000 Pts or $220
Vernon Hills (United States)
Hotel Indigo Chicago-Vernon Hills
From 18,000 Pts or $126
Frequently Asked Questions
The cheapest route from San Diego 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 Diego to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from San Diego to Chicago.
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!
