Our data shows that the cheapest route for a return flight from San Jose to Chicago cost $261 and was between San Jose (SJC) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly from San Jose (SJC) to Chicago Midway Airport (MDW).

Cheap Flights from San Jose (SJC) to Chicago (ORD) start at $36 for one-way and $71 for round trip. Earn your airline miles on top of our rewards!

Fly one-way from San Jose, CA, to Chicago (Midway) starting at $217. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

Find flights to Chicago O'Hare Airport from $34. Fly from San Jose on Spirit Airlines, Frontier and more. Search for Chicago O'Hare Airport flights on KAYAK now to find the best deal.

San Jose (SJC) to Chicago (ORD) flight schedule. The monthly calendar shows every direct flight departure from Norman Y Mineta San Jose International (SJC) with all airlines. Click on a date to see a list of flights or search for the best prices.

Jan 2, 2025 · Find the best deals on flights from San Jose International (SJC) to Chicago O'Hare International (ORD). Compare prices from hundreds of major travel agents and airlines, all in one search.

The best way to get from San Jose to Chicago is to fly which takes 5h 47m and costs $95 - $700. Alternatively, you can train, which costs $190 - $750 and takes 2 days 6h, you could also bus, which costs $180 - $1,100 and takes 2 days 7h.

In the last 3 days, the lowest price for a flight from San Jose to Chicago Midway Airport was $64 for a one-way ticket and $117 for a round-trip.

3 days ago · All direct (non-stop) flights from San Jose to Chicago. See airlines, aircrafts, flight time and distance, flight schedules and timetables.

Find United Airlines cheap flights from San Jose to Chicago. Enjoy a San Jose to Chicago modern flight experience in premium cabins with Wi-Fi.