Route Price Intelligence
Cheap Flights From San Diego to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$415
Great Deal
Under $288
Typical Range
$288 – $424
Lowest We've Seen
$136
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$266
Feb
$288
Mar
$428
Apr
$417
May
$417
Jun
$417
Jul
$437
Aug
—
Sep
—
Oct
$416
Nov
$286
Dec
$316
Cheapest Average Expensive
Best Time to Fly from San Diego to Chicago Midway
The cheapest time to fly from San Diego to Chicago Midway is typically January, when fares average around $266. The most expensive month tends to be July at around $437. For the best deals, consider flying in January, November, February.
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: October9,908 fares analyzedTypical low: $347