Get Me There. San Diego to Chicago
The cheapest round trip from San Diego to Chicago right now is $248 — Aug 12 → 14, 2 nights, 1 stop.
Best fare
Chicago Aug 12 → 14 · 2 nights · 1 stop
$248BOOKBy month
July 2026 $278
August 2026 $248
September 2026 $248
October 2026 $248
All dates (360 priced)
Chicago Aug 12 → 14 · 2 nights · 1 stop
$248BOOKChicago Aug 12 → 15 · 3 nights · 1 stop
$248BOOKChicago Aug 12 → 17 · 5 nights · 1 stop
$248BOOKChicago Aug 13 → 15 · 2 nights · 1 stop
$248BOOKChicago Aug 13 → 17 · 4 nights · 1 stop
$248BOOKChicago Aug 13 → 18 · 5 nights · 1 stop
$248BOOKChicago Aug 20 → 22 · 2 nights · 1 stop
$248BOOKChicago Aug 20 → 23 · 3 nights · 1 stop
$248BOOKChicago Aug 20 → 24 · 4 nights · 1 stop
$248BOOKChicago Aug 20 → 25 · 5 nights · 1 stop
$248BOOKChicago Aug 24 → 26 · 2 nights · 1 stop
$248BOOKChicago Aug 24 → 27 · 3 nights · 1 stop
$248BOOKChicago Aug 24 → 28 · 4 nights · 1 stop
$248BOOKChicago Aug 24 → 29 · 5 nights · 1 stop
$248BOOKChicago Aug 27 → 29 · 2 nights · 1 stop
$248BOOK+345 more dates
Price history
typical $242–$246 · 2 wks of data