Get Me There. San Francisco to Chicago
The cheapest round trip from San Francisco to Chicago right now is $198 — Sep 9 → 11, 2 nights, 1 stop.
Best fare
Chicago Sep 9 → 11 · 2 nights · 1 stop
In the typical range for this route ($178–$237).
Prices checked on Aug 12
By month
August 2026 $200
September 2026cheapest $198
October 2026 $200
November 2026 $200
December 2026 $219
January 2027 $219
February 2027 $219
Get the best San Francisco deals by email — most Fridays, free.
Price history
5 weeks tracked · weekly lows · ↓16% vs 3 wks ago
All dates (719 priced)
Sep 9 → 11 2 nights · 1 stop
Aug 31 → Sep 2 2 nights · 1 stop
Sep 1 → 5 4 nights · 1 stop
Sep 5 → 9 4 nights · 1 stop
Sep 5 → 10 5 nights · 1 stop
Sep 9 → 12 3 nights · 1 stop
Sep 9 → 14 5 nights · 1 stop
Sep 10 → 12 2 nights · 1 stop
Sep 10 → 14 4 nights · 1 stop
Sep 10 → 15 5 nights · 1 stop
The Friday Deal Sheet
The week's best deals from San Francisco, most Fridays — free.