Route Price Intelligence
Cheap Flights From San Diego to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$305
Deals From
$276
Usually Costs
$276 – $320
Lowest We've Seen
$136
Based on 8,315 price pointshigh confidence
Monthly Price Guide
Jan
$357
Feb
$216
Mar
$219
Apr
$187
May
$241
Jun
$310
Jul
$312
Aug
$296
Sep
$305
Oct
$342
Nov
$343
Dec
$392
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 April, when fares average around $187. The most expensive month tends to be December at around $392. 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: $13657 price checksWorst: $204