Get Me There. Oakland to Chicago
The cheapest round trip from Oakland to Chicago right now is $200 — Sep 16 → 21, 5 nights, 1 stop.
Best fare
Chicago Sep 16 → 21 · 5 nights · 1 stop
In the typical range for this route ($178–$237).
Prices checked on Aug 12
By month
August 2026 $239
September 2026cheapest $200
October 2026 $200
November 2026 $200
December 2026 $219
January 2027 $219
February 2027 $219
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Price history
5 weeks tracked · weekly lows · ↓16% vs 3 wks ago
All dates (720 priced)
Sep 16 → 21 5 nights · 1 stop
Sep 17 → 21 4 nights · 1 stop
Sep 23 → 28 5 nights · 1 stop
Sep 24 → 28 4 nights · 1 stop
Sep 24 → 29 5 nights · 1 stop
Sep 28 → Oct 1 3 nights · 1 stop
Sep 29 → Oct 1 2 nights · 1 stop
Sep 30 → Oct 5 5 nights · 1 stop
Oct 1 → 5 4 nights · 1 stop
Oct 1 → 6 5 nights · 1 stop
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