Cheap Flights from Chicago to San Jose Starting at $66

The route Chicago — San Jose is served by many carriers — 6 in total, including American Airlines, United Airlines, Frontier Airlines, Southwest Airlines, Alaska Airlines, and Sun Country Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $66) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.

Chicago is served primarily by two major airports with distinct roles. O’Hare International (ORD) functions as a large international and domestic hub, typically handling legacy carriers like United and American alongside many global airlines; it’s often seen as mid-to-upper range in price due to extensive long-haul connections. Located about 17 miles northwest of downtown, O’Hare is reachable by the CTA Blue Line in roughly 45–60 minutes (fare around $2.50) or by taxis and rideshares in 30–60 minutes depending on traffic (fares vary). Midway (MDW) plays a more domestic and budget-oriented role, commonly used by low-cost carriers such as Southwest; it sits about 10 miles southwest of the Loop, usually a 20–40 minute drive or a 25–35 minute CTA ride on the Orange Line (similar fares). O’Hare offers more international amenities and flight options but can be busier and spread out; Midway is often quicker and simpler for domestic travelers but has fewer nonstop global connections.

San Jose Mineta International Airport (SJC) is the primary commercial gateway for Silicon Valley, functioning as a mid-sized international hub with a mix of full-service carriers (American, United, Delta) and several low-cost or regional operators. Fares from SJC can be competitive for domestic and West Coast routes but often run higher than larger Bay Area airports for transcontinental flights. The airport sits about 3–4 miles northwest of downtown San Jose; a taxi or rideshare typically takes 10–20 minutes depending on traffic, while VTA light rail and bus connections can take 20–35 minutes with low single-ride fares. Parking and short-term options are convenient but can be pricier than public transit. Pros: easy access to tech campuses and a compact terminal layout; cons: fewer late-night international connections and occasionally higher peak-period fares.

In different months, ticket prices from Chicago to San Jose vary: minimum — $163 (February 2026), maximum — $428 (November 2025). Typically, the flight costs $268–$640.