Cheap Flights from Chicago to San Francisco
Cheap Flights from Chicago to San Francisco
Looking for cheap flights from Chicago to San Francisco? 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 Francisco vary by season, cabin, and date, but available award flights can start around 12,500 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 Francisco for specific travel dates.
2026-11-05
ORD - SFO
Economy | 1 Stop
From 12,500 Pts + $5.6
2026-11-05
ORD - SFO
Economy | 1 Stop
From 12,500 Pts + $5.6
2026-11-05
ORD - SFO
Economy | 1 Stop
From 12,500 Pts + $5.6
2026-11-06
ORD - SFO
Economy | 1 Stop
From 12,500 Pts + $5.6
2026-11-05
ORD - SFO
Economy | Non stop | 9+ left
From 12,500 Pts + $25.6
2026-11-05
ORD - SFO
Economy | Non stop | 9+ left
From 12,500 Pts + $25.6
Chicago to San Francisco flight facts
Distance
1,839 mi
2,959 km in a straight line
Estimated flight time
about 4h 15m
In the air, for the straight-line distance
Time difference
−2h
San Francisco is 2 hours behind Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in San Francisco
SFO · San Francisco Intl
Nearby airport alternatives
Flights Chicago - Oakland · Oakland is 11 mi from San Francisco
Flights Chicago - San Jose · San Jose is 30 mi from San Francisco
Flights Chicago - Santa Rosa · Santa Rosa is 66 mi from San Francisco
Flights Milwaukee - San Francisco · Milwaukee is 73 mi from Chicago
Flights Chicago - Monterey · Monterey is 77 mi from San Francisco
Flights Chicago - Sacramento · Sacramento is 86 mi from San Francisco
Premium cabin flights from Chicago to San Francisco
Premium cabin
2026-11-06
ORD - SFO
First | Non stop | 3 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-05
ORD - SFO
First | 1 Stop | 2 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-05
ORD - SFO
First | 1 Stop | 2 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-05
ORD - SFO
First | 1 Stop | 2 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-05
ORD - SFO
Business | 1 Stop
From 43,600 Pts + $5.6
Premium cabin
2026-11-05
ORD - SFO
Business | 1 Stop
From 43,600 Pts + $5.6
Selected hotels for your next stay
Oakland (United States)
Kissel Uptown Oakland
From 12,000 Pts or $207
San Francisco (United States)
Hotel Kabuki
From 15,000 Pts or $245
St Helena (United States)
Alila Napa Valley
From 35,000 Pts or $859
Frequently Asked Questions
The cheapest route from Chicago to San Francisco 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 Francisco.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to San Francisco.
Chicago and San Francisco are about 1,839 miles (2,959 km) apart in a straight line.
Flying the 1,839-mile straight-line distance takes about 4h 15m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
San Francisco is 2 hours behind Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in San Francisco: San Francisco Intl (SFO).
Travelers searching this route also look at other popular routes into San Francisco, plus the return trip when we track it. Fares and award space change daily.
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points travel planning experience. Yeah!
