San Francisco (SFO) to Chicago (CHI): 1,842 miles (2,964 km) great-circle, about 4h 10m nonstop by our estimate. Cheapest fare observed: $364 round-trip on Alaska Airlines, with 1 stop, departing April 25, 2026.
$364 round-trip, Alaska Airlines AS2349, departing 2026-04-25 at 10:10, returning 2026-04-25. The recorded itinerary left on a Saturday and came back the same day; the fare was observed 0 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $364, it ranked 11th of the 30 round-trip fares we recorded from SFO (median $646). That is 19.8 cents per great-circle mile (round-trip price over one-way distance), above the SFO median of 16.9 cents across 30 round-trip routes.
Routes from SFO of similar length: Mexico City (1,882 mi) at $433 and Toronto (2,254 mi) at $358.
Alaska Airlines had the cheapest fare on 7 of 30 SFO routes. It is the 26th longest of the 30 routes we track from SFO.
Of 33 departure airports with a fare to Chicago, San Francisco (SFO) ranked 29th at $364. Lowest: $89 from Atlanta (ATL); highest: $1241 from Nairobi (NBO); 16 nonstop. Cheapest-fare airlines (routes): Frontier (15), Spirit (5), United Airlines (4), American Airlines (2), airline 0O (1) and Alaska Airlines (1), plus 5 more.
Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Los_Angeles, America/Chicago; flight time is our estimate.