Route Price Intelligence
Cheap Flights From San Diego to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$347
Deals From
$337
Usually Costs
$337 – $367
Lowest We've Seen
$136
Based on 8,529 price pointshigh confidence
Monthly Price Guide
Jan
$387
Feb
$493
Mar
$567
Apr
$271
May
$277
Jun
$347
Jul
$350
Aug
$347
Sep
$347
Oct
$357
Nov
$393
Dec
$387
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 $271. The most expensive month tends to be March at around $567. For the best deals, consider flying in April, May, June.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $13686 price checksWorst: $251