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 travel times in Rome2Rio's travel planner.

The cheapest ticket to Illinois from San Diego found in the last 72 hours was $38 one-way, and $87 round-trip. The most popular route is from San Diego to Chicago O'Hare Intl , and the cheapest round-trip airline ticket found on this route in the last 72 hours was $33.

Fly one-way from San Diego to Chicago (O'Hare) starting at $181. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

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.

Explore weekly flight availability from San Diego to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey.

Fly one-way from San Diego to Chicago (Midway) starting at $171. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

The best way to get from San Diego to Chicago is to fly which takes 5h 41m and costs $60 - $460. Alternatively, you can train, which costs $190 - $700 and takes 46h 3m, you could also bus, which costs $170 - $1,000 and takes 2 days 3h.

The best way to get from Illinois to San Diego is to fly which takes 6h 40m and costs $65 - $430. Alternatively, you can train, which costs $190 - $700 and takes 46h 7m, you could also bus, which costs $160 - $1,000 and takes 2 days 2h.

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 see a list of flights or search for the best prices.

Book your next Greyhound bus from San Diego, CA to Chicago, IL. Get free Wi-Fi & plug outlets on board, extra legroom and 2 pieces of free luggage.