Get Me There. Oakland to Chicago
The cheapest round trip from Oakland to Chicago right now is $218 — Sep 23 → 28, 5 nights, 1 stop.
Best fare
Chicago Sep 23 → 28 · 5 nights · 1 stop
In the typical range for this route ($173–$223).
Prices checked on Sep 2
By month
September 2026cheapest $218
October 2026 $237
November 2026 $266
December 2026 $257
January 2027 $257
February 2027 $257
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Price history
8 weeks tracked · weekly lows
All dates (720 priced)
Sep 23 → 28 5 nights · 1 stop
Sep 24 → 28 4 nights · 1 stop
Oct 3 → 7 4 nights · 1 stop
Sep 24 → 29 5 nights · 1 stop
Sep 26 → 28 2 nights · 1 stop
Oct 3 → 5 2 nights · 1 stop
Oct 3 → 6 3 nights · 1 stop
Sep 24 → 26 2 nights · 1 stop
Sep 22 → 25 3 nights · 1 stop
Sep 23 → 25 2 nights · 1 stop
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