Cheap Flights from Chicago to Santa Rosa
Cheap Flights from Chicago to Santa Rosa
Looking for cheap flights from Chicago to Santa Rosa? 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 Santa Rosa vary by season, cabin, and date, but available award flights can start around 17,500–43,600 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 Santa Rosa for specific travel dates.
2026-11-30
ORD - STS
Economy | 1 Stop | 9+ left
From 17,500 Pts + $31.2
2026-11-30
ORD - STS
Economy | 1 Stop
From 18,500 Pts + $5.6
2026-11-30
ORD - STS
First | 2 Stops | 1 left
From 25,000 Pts + $11.2
Chicago to Santa Rosa flight facts
Distance
1,841 mi
2,963 km in a straight line
Estimated flight time
about 4h 15m
In the air, for the straight-line distance
Time difference
−2h
Santa Rosa is 2 hours behind Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Santa Rosa
STS · Charles M. Schulz Sonoma County
Nearby airport alternatives
Flights Chicago - Oakland · Oakland is 63 mi from Santa Rosa
Flights Chicago - San Francisco · San Francisco is 66 mi from Santa Rosa
Flights Chicago - Sacramento · Sacramento is 67 mi from Santa Rosa
Flights Chicago - San Jose · San Jose is 93 mi from Santa Rosa
Flights Chicago - Monterey · Monterey is 143 mi from Santa Rosa
Flights Chicago - Reno · Reno is 177 mi from Santa Rosa
Premium cabin flights from Chicago to Santa Rosa
Premium cabin
2026-11-30
ORD - STS
First | 1 Stop
From 43,600 Pts + $5.6
Premium cabin
2026-11-30
ORD - STS
First | 2 Stops | 1 left
From 25,000 Pts + $11.2
Premium cabin
2026-11-30
ORD - STS
First | 1 Stop | 1 left
From 35,000 Pts + $25.6
Selected hotels for your next stay
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Frequently Asked Questions
The cheapest route from Chicago to Santa Rosa 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 Santa Rosa.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Santa Rosa.
Chicago and Santa Rosa are about 1,841 miles (2,963 km) apart in a straight line.
Flying the 1,841-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.
Santa Rosa is 2 hours behind Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Santa Rosa: Charles M. Schulz Sonoma County (STS).
Travelers searching this route also look at other popular routes into Santa Rosa, plus the return trip when we track it. Fares and award space change daily.
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points travel planning experience. Yeah!
