* All fares below were last found on: Jul 17, 2018 and 8:42:28 PM.
Fares are round trip, Fares incl. all fuel surcharges, our service fees and taxes.
Displayed fares are based on historical data, are subject to change and cannot be guaranteed at the time of booking.
See all booking terms and conditions
Find the deals you want & manage your trips ... all while on the go.
Earn rewards points & other travel perks when you spend.
Get inspired, learn expert tips & add to your travel bucket list.
Fatherly Advice: 7 Cities That Are Just Perfect for a Trip with Dad
Perfect for Pals! The Best Destinations to Visit with Your BFF
Sun’s Out, Fun’s Out! 8 Weekend Getaways to Perk Up Your Summer
How to Have Fun with the Grandkids in These 5 Cities
Enter the Rooster: The 5 Best US Cities to Celebrate the Chinese New Year
Book your flights from San Diego to Chicago and save big on airfares. Chicago is known as "Chi-town", "Windy City," "Second City" and is the third most populous city in the United States. The city has some amazing museums and cultural institutions that are counted among the best in the world. Art Institute of Chicago should not be missed while on a trip to Chicago.
To reach San Diego to Chicago, you may choose amongst the top airlines such as Sun Country, Sun Country and Frontier Airlines. Take advantage of exclusive deals on flights to Chicago and save more to splurge on a vacation. Your flight to San Diego to Chicago takes about five hours twenty eight minutes to cover a distance of about 1,729 miles excluding layover time, make sure to carry an IPod or an mp3 player to keep yourself entertained.