Cheap Flights from San Diego (SAN) to Chicago (ORD) start at $52 for one-way and $83 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.

Flights from San Diego to Chicago. Use Google Flights to plan your next trip and find cheap one way or round trip flights from San Diego to Chicago. Find the best flights fast, track...

Our data shows that the cheapest route for a return flight from San Diego to Chicago cost $265 and was between San Diego (SAN) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly from San Diego (SAN) to Chicago Midway Airport (MDW).

Fly one-way from San Diego to Chicago (Midway) starting at $236. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

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

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.

San Diego International Airport (SAN) to Chicago Midway International Airport (MDW) is the most popular route. There are 15 direct departures a week to choose from. If you prefer starting your day later, hop on the last flight with Southwest Airlines at 19:05.

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from San Diego to O'Hare Intl. Discover the best prices and deals for you by selecting your travel dates. Only flying one-way? Below are some of the best one-way flight deals from San Diego to O'Hare Intl found on KAYAK recently.

Jan 23, 2025 · Find airfare and ticket deals for cheap flights from San Diego to Chicago O'Hare Intl Airport. Search flight deals from various travel partners with one click at $75.