Get Me There. Oakland to Chicago
1,831 mi · 1 stop The cheapest round trip from Oakland to Chicago right now is $201 — Dec 12 → 15, 3 nights, 1 stop.
Best fare
Chicago Dec 12 → 15 · 3 nights · 1 stop
In the typical range for this route ($178–$218).
Prices checked on Oct 12
By month
October 2026 $334
November 2026 $270
December 2026cheapest $201
January 2027 $247
February 2027 $269
March 2027 $349
April 2027 $365
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Price history
13 weeks tracked · weekly lows
All dates (720 priced)
Dec 12 → 15 3 nights · 1 stop
Dec 10 → 15 5 nights · 1 stop
Dec 11 → 15 4 nights · 1 stop
Jan 7 → 11 4 nights · 1 stop
Dec 1 → 5 4 nights · 1 stop
Dec 2 → 5 3 nights · 1 stop
Dec 5 → 8 3 nights · 1 stop
Dec 5 → 9 4 nights · 1 stop
Dec 12 → 16 4 nights · 1 stop
Feb 3 → 8 5 nights · 1 stop
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