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

Cheap Flights from San Jose (SJC) to Chicago (ORD) start at $36 for one-way and $70 for round trip. Earn your airline miles on top of our rewards!

Fly one-way from San Jose, CA, to Chicago (Midway) starting at $176. 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 $49. 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.

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.

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.

The cheapest month for flights from San Jose to Chicago Midway Airport is March, where tickets cost $236 (return) on average. On the other hand, the most expensive months are April and June, where the average cost of round-trip tickets is $612 and $587 respectively.

Get recent, data-driven insights about flights from San Jose to Chicago including ideal travel times, pricing trends, and more. How far ahead should I book a flight from San Jose to Chicago? The best time to book flights from San Jose to Chicago is …

Dec 30, 2024 · Cheap flights from San Jose to Chicago (SJC - CHI): Compare last minute flight deals, direct flights and round-trip flights with Orbitz today!

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.