Get Me There. Oakland to Chicago
1,831 mi · 1 stop The cheapest round trip from Oakland to Chicago right now is $180 — Dec 2 → 7, 5 nights, 1 stop.
Best fare
Chicago Dec 2 → 7 · 5 nights · 1 stop
In the typical range for this route ($168–$215).
Prices checked on Oct 20
By month
October 2026 $402
November 2026 $193
December 2026cheapest $180
January 2027 $227
February 2027 $296
March 2027 $385
April 2027 $385
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Price history
15 weeks tracked · weekly lows↓15% vs 3 wks ago
All dates (714 priced)
Dec 2 → 7 5 nights · 1 stop
Nov 12 → 16 4 nights · 1 stop
Dec 3 → 7 4 nights · 1 stop
Dec 3 → 5 2 nights · 1 stop
Dec 3 → 8 5 nights · 1 stop
Dec 5 → 7 2 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
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