Cheap Flights from San Jose to Chicago Starting at $96

The San Jose — Chicago route is served by a wide range of airlines: 6 in total, including United Airlines, Southwest Airlines, American Airlines, Frontier Airlines, Alaska Airlines, and Grumeti Air. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $96. Our service helps compare all available offers within seconds and choose the most convenient option. You can filter flights by price, departure time, or baggage rules to make your trip as comfortable as possible. With so many airlines, there’s always a chance to catch special promotions and save.

San Jose Mineta International Airport (SJC) serves as the primary commercial gateway to Silicon Valley and typically functions as a mid-sized international and domestic hub rather than a major long-haul connector. You’ll often find a mix of legacy carriers and low-cost airlines operating regional and transcontinental routes, with occasional international services. The airport sits about 3–5 miles from downtown San Jose; taxi or rideshare trips usually take 10–20 minutes depending on traffic and can be moderate in cost, while the VTA light rail and shuttle options are cheaper but slower (roughly 20–35 minutes). Pros include compact terminals and short walking distances; potential downsides are limited late-night international frequencies and occasional peak-hour congestion.

Chicago is served by two main airports with distinct roles. O’Hare International (ORD) is the city’s largest international and connecting hub, typically hosting major network carriers and many long-haul flights; it can be perceived as mid-to-high priced compared with secondary airports. O’Hare lies about 17 miles northwest of downtown, reachable by CTA Blue Line in roughly 45–60 minutes for a modest fare, or by taxi/ride-share in 30–60 minutes depending on traffic with higher costs. Pros: extensive international connections and amenities; Cons: busy terminals and longer transfer times at peak hours. Midway Airport (MDW) acts as Chicago’s smaller, more budget-friendly option, often favored by low-cost and domestic carriers offering value-oriented fares. Located about 10 miles southwest of the Loop, Midway is typically a quicker drive—around 20–35 minutes without heavy traffic—and connected by the CTA Orange Line in roughly 25–35 minutes for a low fare. Pros: compact terminals and shorter walking times; Cons: fewer international routes and sometimes limited late-night service. Both airports provide rental cars, shuttles, and ground transportation options, with travel times and costs varying by time of day and service choice.

The minimum one-way ticket price from San Jose to Chicago is $212 (March 2026), while the maximum is $303 (November 2025). On average, a ticket costs $241–$243.