Cheap Flights from San Francisco to Chicago — $100

More than 5 airlines operate flights from San Francisco to Chicago, including United Airlines, American Airlines, Southwest Airlines, Frontier Airlines, and JetHunter. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $100, and our service lets you instantly compare all options. The variety of offers simplifies planning: you can choose budget fares or more comfortable options with baggage included or extra services. We help you find the best deals so your trip is cost-efficient.

The cost of a one-way flight from San Francisco to Chicago ranges from $86 (May 2026) to $129 (July 2026). On average, the ticket price is about $111–$245.

Fly direct from San Francisco to Chicago for the fastest, most convenient way to get between these two major hubs — fewer hassles, no long layovers, and more time to enjoy the Windy City. While connecting flights can sometimes be cheaper, choosing a nonstop saves valuable time and delivers a more comfortable, reliable travel experience.

Fly from San Francisco to Chicago with confidence — our search scans over 700 airlines, 50+ travel agencies and 5+ leading booking systems to surface the best prices, schedules and travel conditions for your trip. Compare nonstop and connecting options in seconds and lock in the fare that fits your timetable and budget.

San Francisco International (SFO) is the region’s main international gateway and a major transpacific hub, typically serving full-service carriers alongside some low-cost and domestic services. Located about 13 miles south of downtown San Francisco, it’s usually reached by BART (roughly 30–45 minutes, fares commonly in the low-to-mid single digits) or airport shuttles, taxis and rideshares (30–60 minutes depending on traffic; fares vary). Travelers can expect a full range of facilities and long-haul connections but sometimes heavier passenger flows and higher on-site prices than smaller airports. For quick Bay Area access consider nearby Oakland or San Jose airports for alternative budget or domestic options.

Chicago is served by two primary airports and several smaller fields. O’Hare International (ORD) is the city’s main international hub, typically hosting most long-haul and legacy-carrier flights from United/United Express, American, and numerous global airlines; fares can be mid-to-high depending on demand. It sits roughly 17–18 miles northwest of downtown and is usually reached by CTA Blue Line trains (about 45–55 minutes, fares around the cost of a standard transit ride) or by car/taxi rides that often take 30–60 minutes depending on traffic, with ride-share/airport shuttle costs varying. O’Hare offers extensive amenities and frequent services but can be busy and spread out, which may mean longer connection or walk times. Midway Airport (MDW) operates more as a domestic and low-cost focused airport, commonly serving carriers like Southwest and some low-cost/short-haul airlines; it is about 10 miles southwest of the Loop. Ground options include CTA Orange Line trains (roughly 25–35 minutes, standard transit fare) and taxis or ride-shares that usually take 20–45 minutes and tend to be cheaper than long-haul transfers. Midway is often perceived as more budget-friendly and compact, making connections and terminal navigation quicker, though it has fewer international services and potentially more limited late-night options.