Cheap Flights from Chicago to Oakland
Cheap Flights from Chicago to Oakland
Looking for cheap flights from Chicago to Oakland? 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 Oakland vary by season, cabin, and date, but available award flights can start around 12,500–15,000 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 Chicago to Oakland for specific travel dates.
2026-11-07
ORD - OAK
Economy | 1 Stop
From 12,500 Pts + $5.6
2026-11-22
ORD - OAK
Economy | 2 Stops
From 12,500 Pts + $5.6
2026-12-24
ORD - OAK
Economy | 2 Stops
From 12,500 Pts + $5.6
2026-12-25
ORD - OAK
Economy | 2 Stops | 2 left
From 12,500 Pts + $5.6
2026-11-21
ORD - OAK
Economy | 2 Stops
From 12,500 Pts + $11.2
2026-12-23
ORD - OAK
Economy | 1 Stop | 9+ left
From 15,000 Pts + $11.2
Chicago to Oakland flight facts
Distance
1,828 mi
2,942 km in a straight line
Estimated flight time
about 4h 15m
In the air, for the straight-line distance
Time difference
−2h
Oakland is 2 hours behind Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Oakland
OAK · Metropolitan Oakland Intl
Nearby airport alternatives
Flights Chicago - San Francisco · San Francisco is 11 mi from Oakland
Flights Chicago - San Jose · San Jose is 29 mi from Oakland
Flights Chicago - Santa Rosa · Santa Rosa is 63 mi from Oakland
Flights Chicago - Sacramento · Sacramento is 75 mi from Oakland
Flights Chicago - Monterey · Monterey is 81 mi from Oakland
Flights Chicago - Fresno · Fresno is 152 mi from Oakland
Premium cabin flights from Chicago to Oakland
Premium cabin
2026-11-07
ORD - OAK
First | 1 Stop | 2 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-08
ORD - OAK
First | 1 Stop | 5 left
From 35,000 Pts + $31.2
Premium cabin
2026-11-21
ORD - OAK
First | 1 Stop | 5 left
From 35,000 Pts + $31.2
Premium cabin
2026-12-24
ORD - OAK
First | 1 Stop | 1 left
From 42,500 Pts + $5.6
Premium cabin
2026-12-25
ORD - OAK
First | 1 Stop | 9+ left
From 42,500 Pts + $11.2
Premium cabin
2026-11-22
ORD - OAK
First | 1 Stop | 3 left
From 45,000 Pts + $25.6
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 Oakland 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 Oakland.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Oakland.
Chicago and Oakland are about 1,828 miles (2,942 km) apart in a straight line.
Flying the 1,828-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.
Oakland is 2 hours behind Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Oakland: Metropolitan Oakland Intl (OAK).
Travelers searching this route also look at other popular routes into Oakland, plus the return trip when we track it. Fares and award space change daily.
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