Get Me There. San Diego to Chicago
The cheapest round trip from San Diego to Chicago right now is $166 — Sep 5 → 9, 4 nights, 1 stop.
Best fare
Chicago Sep 5 → 9 · 4 nights · 1 stop
Below typical ($192–$240) — this is a good fare.
Prices checked on Aug 12
By month
August 2026 $206
September 2026cheapest $166
October 2026 $166
November 2026 $166
December 2026 $243
January 2027 $226
February 2027 $235
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Price history
5 weeks tracked · weekly lows · ↓31% vs 3 wks ago
All dates (715 priced)
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 12 → 14 2 nights · 1 stop
Sep 12 → 15 3 nights · 1 stop
Sep 12 → 16 4 nights · 1 stop
Sep 14 → 16 2 nights · 1 stop
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