Route Price Intelligence
Cheap Flights From San Francisco Bay Area to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
⭐ Great DealFound 1d ago
$187Silicon Valley to the Windy City for $187 on Frontier! Chicago's architecture, deep-dish pizza, and culture scene make for a perfect long weekend.
✓ 7 date combinations found at this price
Search Google FlightsTypical Price
$295
Deals From
$241
Usually Costs
$241 – $324
Lowest We've Seen
$125
Based on 8,266 price pointshigh confidence
Monthly Price Guide
Jan
$401
Feb
$239
Mar
$245
Apr
$217
May
$275
Jun
$313
Jul
$313
Aug
$304
Sep
$302
Oct
$302
Nov
$303
Dec
$304
Cheapest Average Expensive
Best Time to Fly from San Francisco Bay Area to Chicago
The cheapest time to fly from San Francisco Bay Area to Chicago is typically April, when fares average around $217. The most expensive month tends to be January at around $401. For the best deals, consider flying in April, February, March.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $12561 price checksWorst: $215