Get Me There. Oakland to Chicago
1,831 mi · 1 stop The cheapest round trip from Oakland to Chicago right now is $209 — Dec 2 → 5, 3 nights, 1 stop.
Best fare
Chicago Dec 2 → 5 · 3 nights · 1 stop
In the typical range for this route ($168–$225).
Prices checked on Sep 22
By month
September 2026 $363
October 2026 $263
November 2026 $263
December 2026cheapest $209
January 2027 $252
February 2027 $289
March 2027 $337
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Price history
11 weeks tracked · weekly lows
All dates (720 priced)
Dec 2 → 5 3 nights · 1 stop
Dec 2 → 4 2 nights · 1 stop
Dec 5 → 9 4 nights · 1 stop
Dec 8 → 12 4 nights · 1 stop
Dec 2 → 7 5 nights · 1 stop
Dec 8 → 10 2 nights · 1 stop
Dec 5 → 8 3 nights · 1 stop
Dec 5 → 10 5 nights · 1 stop
Dec 2 → 6 4 nights · 1 stop
Jan 7 → 11 4 nights · 1 stop
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