Cheap flights from San Jose to Chicago from $56

SJC is the main airport in San Jose, serving most flights in and out of the city. The airport is well-connected to downtown and has many transport options, including a train to downtown. You can get domestic and international flights from SJC, including direct flights to Chicago offered by Alaska Airlines and Southwest. Its compact size makes it easy to clear security, with wait times of less than 20min. Moreover, you’ll have plenty of amenities to enjoy, including free Wi-Fi. The two airports serving flights from San Jose to Chicago are ORD and MDW, and each has its benefits. If you want easier access to downtown, MDW is the better option as it is closer, and transportation fares are much cheaper. Moreover, you’ll have an easier time getting through security at MDW. However, ORD is a much larger airport, offering many domestic and international flights, and offers travelers more flexibility. ORD also has more amenities than MDW, including premium lounges like Polaris.

SJC is well-connected to downtown San Jose, and there are many transport options to and from downtown. The first option is car rentals, and many rental agencies, including Hertz, Avis, Budget, Thrifty, Enterprise, and Alamo, have rental counters at SJC. Taxis are another option, available outside Terminals A and B. All are metered, and prior reservations aren’t required. Shared-ride shuttles are also available, and they provide door-to-door services to and from the airport. You can get these shuttles at the Terminal A parking garage. The final option is the train; the Airport Flyer has frequent trips from Santa Clara Caltrain Station. Similarly, you’ll have many options from Chicago airports to downtown. The first is bus transportation; CTA buses offer regular trips downtown, while the PACE buses serve the Chicago suburbs. Another cheap option is the CTA Blue Line, or the "L" train, operating 24h between Chicago airports and downtown. Taxis are also available curbside, and car rentals are available at Chicago airports, with companies like Avis, Thrifty, Hertz, National, Alamo, Avis, Budget, and SIXT at both ORD and MDW.

Several cities are within driving distance of both Chicago airports, and a rental car will be the best way of getting to these cities. You can rent cars at Midway and O’Hare and drive to many cities from Chicago in less than 3h, including Michigan City, Milwaukee, Grand Rapids, South Bend, Indianapolis, and Ann Arbor. You also can take regional buses available at ORD, which offer regional service to Iowa, Illinois, Wisconsin, and Indiana.