Route Price Intelligence
Cheap Flights From Chicago to Oakland
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$368
Deals From
$334
Usually Costs
$334 – $409
Lowest We've Seen
$159
Based on 8,320 price pointshigh confidence
Monthly Price Guide
Jan
$375
Feb
$364
Mar
$492
Apr
$310
May
$325
Jun
$389
Jul
$396
Aug
$373
Sep
$355
Oct
$356
Nov
$375
Dec
$464
Cheapest Average Expensive
Best Time to Fly from Chicago to Oakland
The cheapest time to fly from Chicago to Oakland is typically April, when fares average around $310. The most expensive month tends to be March at around $492. For the best deals, consider flying in April, May, September.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $15989 price checksWorst: $271