Route Price Intelligence
Cheap Flights From San Diego to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
🔥 Fire DealFound 3d ago
$166San Diego to Chicago usually costs around $347 round trip, now down to $166 on Frontier. That is a strong price for deep dish, lakefront views, and world class museums, with plenty of flight options this fall to fit your schedule.
✓ 10 date combinations found at this price
Search Google FlightsTypical Price
$347
Great Deal
Under $166
Typical Range
$166 – $347
Lowest We've Seen
$95
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$347
Feb
—
Mar
—
Apr
$361
May
$250
Jun
$270
Jul
$290
Aug
$270
Sep
$347
Oct
$347
Nov
$347
Dec
$347
Cheapest Average Expensive
Best Time to Fly from San Diego to Chicago
The cheapest time to fly from San Diego to Chicago is typically May, when fares average around $250. The most expensive month tends to be April at around $361. For the best deals, consider flying in May, June, August.
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: August17,759 fares analyzedTypical low: $285