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 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 Chicago to San Diego for specific travel dates.
2026-04-22
ORD - SAN
Economy | 1 Stop
From 12,500 Pts + $5.6
2026-04-22
ORD - SAN
Economy | Non stop | 5 left
From 15,000 Pts + $5.6
2026-04-22
ORD - SAN
Economy | Non stop | 5 left
From 17,880 Pts + $30.6
2026-04-22
ORD - SAN
Economy | Non stop
From 20,700 Pts + $5.6
2026-04-22
ORD - SAN
Economy | Non stop | 5 left
From 15,000 Pts + $34
2026-04-22
ORD - SAN
Economy | Non stop | 5 left
From 19,000 Pts + $10.2
Premium cabin flights from Chicago to San Diego
Premium cabin
2026-04-22
ORD - SAN
First | 1 Stop
From 34,000 Pts + $5.6
Premium cabin
2026-04-23
ORD - SAN
First | Non stop | 9+ left
From 25,000 Pts + $18.1
Premium cabin
2026-04-23
ORD - SAN
Business | Non stop
From 43,600 Pts + $5.6
Premium cabin
2026-04-23
ORD - SAN
First | Non stop
From 22,000 Pts + $5.6
Premium cabin
2026-04-24
ORD - SAN
First | Non stop | 1 left
From 25,000 Pts + $18.1
Premium cabin
2026-04-24
ORD - SAN
Business | Non stop
From 43,600 Pts + $5.6
Selected hotels for your next stay
Dana Point, CA (USA)
Waldorf Astoria Monarch Beach
From 95,000 Pts or $669
Rancho Santa Fe (USA)
The Inn at Rancho Santa Fe, an SLH Hotel
From 110,000 Pts or $441
San Diego (United States)
Hotel Indigo San Diego-Gaslamp Quarter
From Pts or $257
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.
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Our mission is to provide the simplest and best
points travel planning experience. Yeah!
