Cheap Flights from Santa Rosa to Chicago
Cheap Flights from Santa Rosa to Chicago
Looking for cheap flights from Santa Rosa 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 Santa Rosa to Chicago vary by season, cabin, and date, but available award flights can start around 9,000–25,000 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 Santa Rosa to Chicago for specific travel dates.
2026-11-25
STS - ORD
Economy | 2 Stops
From 9,000 Pts + $5.6
2026-11-25
STS - ORD
Economy | 1 Stop | 4 left
From 17,500 Pts + $31.2
2026-11-24
STS - ORD
Economy | 2 Stops
From 20,500 Pts + $5.6
2026-11-25
STS - ORD
Economy | 1 Stop
From 20,700 Pts + $11.2
2026-11-24
STS - ORD
First | 2 Stops | 4 left
From 25,000 Pts + $5.6
2026-11-25
STS - ORD
First | 2 Stops | 4 left
From 25,000 Pts + $5.6
Santa Rosa to Chicago 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
Chicago is 2 hours ahead of Santa Rosa.
Airports in Santa Rosa
STS · Charles M. Schulz Sonoma County
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights San Francisco - Chicago · San Francisco is 66 mi from Santa Rosa
Flights Sacramento - Chicago · Sacramento is 67 mi from Santa Rosa
Flights San Jose - Chicago · San Jose is 93 mi from Santa Rosa
Flights Reno - Chicago · Reno is 177 mi from Santa Rosa
Premium cabin flights from Santa Rosa to Chicago
Premium cabin
2026-11-24
STS - ORD
First | 1 Stop | 3 left
From 35,000 Pts + $31.2
Premium cabin
2026-11-24
STS - ORD
Business | 1 Stop
From 43,600 Pts + $11.2
Premium cabin
2026-11-24
STS - ORD
First | 2 Stops | 4 left
From 25,000 Pts + $5.6
Premium cabin
2026-11-25
STS - ORD
First | 2 Stops | 4 left
From 25,000 Pts + $5.6
Premium cabin
2026-11-25
STS - ORD
First | 1 Stop | 3 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-25
STS - ORD
Business | 1 Stop
From 43,600 Pts + $5.6
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
Frequently Asked Questions
The cheapest route from Santa Rosa 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 Santa Rosa to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Santa Rosa to Chicago.
Santa Rosa and Chicago 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.
Chicago is 2 hours ahead of Santa Rosa.
Departures from Santa Rosa: Charles M. Schulz Sonoma County (STS). Arrivals in Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD).
Travelers searching this route also look at other popular routes into Chicago, plus the return trip when we track it. Fares and award space change daily.
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