Cheap Flights from San Francisco to Chicago
Compare cheap flights from San Francisco (SFO) to Chicago (ORD) on Tripile, with fares from around $139. The route takes about 4h 15m, and October is often the best month for low prices.
Airlines on This Route
Popular airlines flying San Francisco to Chicago include United, American Airlines, Spirit, Delta. Compare their schedules, baggage rules, and prices side by side, then book the option that fits your trip.
With 4 carriers commonly serving SFO to ORD, departure times are spread across the day, so it is worth checking early-morning and late-evening flights when you want the lowest fare on a 4h 15m sector.
When to Book SFO to ORD
Fares on this route start from around $139, and October typically brings the lowest prices. Search with flexible dates to compare a whole month at once, check the return leg from Chicago to San Francisco in the same search, and review the fare rules before paying so you know what a change or cancellation would cost.