Every Chicago–Washington fare we track, measured against the route's typical price whenever there is enough cached history to build one. Subscribe in any RSS reader for free single-route price alerts — no account, no email needed.https://flight.dealsen-ushttps://flight.deals/flights/chicago-to-washington/#2026-10-07-2026-11-03-WNhttps://flight.deals/flights/chicago-to-washington/#2026-10-07-2026-11-03-WNCHI → WAS round-trip on Southwest, 2026-10-07 to 2026-11-03 (27 nights). Cached fare $159. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMT