Cheap Flights from Chicago to San Diego
Looking for cheap flights from Chicago to San Diego? 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 Diego vary by season, cabin, and date, but available award flights can start around 8,500 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 Diego for specific travel dates.
2026-09-26
ORD - SAN
Economy | Non stop
From 8,500 Pts + $5.6
2026-09-28
ORD - SAN
Economy | Non stop
From 8,500 Pts + $5.6
2026-09-29
ORD - SAN
Economy | Non stop
From 8,500 Pts + $5.6
2026-09-30
ORD - SAN
Economy | Non stop
From 8,500 Pts + $5.6
2026-10-01
ORD - SAN
Economy | Non stop
From 8,500 Pts + $5.6
2026-10-02
ORD - SAN
Economy | Non stop
From 8,500 Pts + $5.6
Premium cabin flights from Chicago to San Diego
Premium cabin
2026-09-19
ORD - SAN
First | Non stop
From 18,500 Pts + $5.6
Premium cabin
2026-09-20
ORD - SAN
First | 1 Stop
From 18,500 Pts + $5.6
Premium cabin
2026-09-11
ORD - SAN
First | Non stop
From 20,000 Pts + $5.6
Premium cabin
2026-09-12
ORD - SAN
First | Non stop
From 20,000 Pts + $5.6
Premium cabin
2026-09-13
ORD - SAN
First | 1 Stop
From 20,000 Pts + $5.6
Premium cabin
2026-09-15
ORD - SAN
First | Non stop
From 20,000 Pts + $5.6
Selected hotels for your next stay
Encinitas (United States)
Alila Marea Beach Resort Encinitas
From 25,000 Pts or $729
San Diego, CA (USA)
The Westin San Diego Bayview
From 41,000 Pts
San Diego, CA (USA)
The Guild Hotel, San Diego, a Tribute Portfolio Hotel
From 47,000 Pts
Frequently Asked Questions
The cheapest route from Chicago to San Diego 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 Diego.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to San Diego.
Our mission is to provide
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Our mission is to provide the simplest and best
points travel planning experience. Yeah!
