Fly one-way from San Diego to Chicago (O'Hare) starting at $180. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

Cheap Flights from San Diego (SAN) to Chicago (ORD) start at $33 for one-way and $68 for round trip. Earn your airline miles on top of our rewards!

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

There are 7 ways to get from San Diego to Illinois by plane, train (Amtrak), bus (Greyhound), car, or train. Select an option below to see step-by-step directions and to compare ticket prices and …

The cheapest ticket to Illinois from San Diego found in the last 72 hours was $43 one-way, and $95 round-trip. The most popular route is from San Diego to Chicago O'Hare Intl , and the …

The best way to get from San Diego to Chicago is to fly which takes 5h 41m and costs $60 - $550. Alternatively, you can train, which costs $190 - $700 and takes 46h 3m, you could also bus, …

San Diego (SAN) to Chicago (ORD) flight schedule. The monthly calendar shows every direct flight departure from San Diego International Airport (SAN) with all airlines. Click on a date to …

Cheap Flight Deals from San Diego to Chicago (SAN-CHI) Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Diego to …

Are you searching for American Airlines flights from San Diego to Chicago? Find the best selections and fly in style.

Flights between San Diego, CA and Chicago, IL starting at $77. Choose between United Airlines, Alaska Airlines, or Spirit Airlines to find the best price. Search, compare, and book flights to …