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
$182Frontier's San Jose to Chicago fare usually runs around $347, so $182 marks a strong discount for fall and winter travel. It's a one-stop routing, but Chicago's deep dish, architecture tours, and holiday markets make it worth the calendar space.
✓ 3 date combinations found at this price
Search Google FlightsTypical Price
$347
Great Deal
Under $182
Typical Range
$182 – $372
Lowest We've Seen
$168
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$347
Feb
—
Mar
—
Apr
$462
May
$326
Jun
$314
Jul
$355
Aug
$325
Sep
$347
Oct
$347
Nov
$347
Dec
$388
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 June, when fares average around $314. The most expensive month tends to be April at around $462. For the best deals, consider flying in June, August, May.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route
Cheapest month: August50,613 fares analyzedTypical low: $290