Get Me There. Oakland to Chicago
The cheapest round trip from Oakland to Chicago right now is $244 — Sep 3 → 7, 4 nights, 1 stop.
Best fare
Chicago Sep 3 → 7 · 4 nights · 1 stop
$244BOOKBy month
July 2026 $553
August 2026 $247
September 2026 $244
October 2026 $244
All dates (360 priced)
Chicago Sep 3 → 7 · 4 nights · 1 stop
$244BOOKChicago Sep 10 → 14 · 4 nights · 1 stop
$244BOOKChicago Sep 10 → 15 · 5 nights · 1 stop
$244BOOKChicago Sep 12 → 14 · 2 nights · 1 stop
$244BOOKChicago Sep 12 → 15 · 3 nights · 1 stop
$244BOOKChicago Oct 2 → 5 · 3 nights · 1 stop
$244BOOKChicago Oct 3 → 5 · 2 nights · 1 stop
$244BOOKChicago Oct 5 → 10 · 5 nights · 1 stop
$244BOOKChicago Oct 7 → 10 · 3 nights · 1 stop
$244BOOKChicago Aug 19 → 24 · 5 nights · Nonstop
$247BOOKChicago Aug 20 → 24 · 4 nights · 1 stop
$247BOOKChicago Aug 24 → 26 · 2 nights · Nonstop
$247BOOKChicago Aug 24 → 27 · 3 nights · Nonstop
$247BOOKChicago Aug 24 → 29 · 5 nights · Nonstop
$247BOOKChicago Aug 26 → 31 · 5 nights · 1 stop
$247BOOK+345 more dates
Price history
typical $239–$242 · 2 wks of data