Open interactive map →Cheap flights from Chicago to San Diego
The Chicago to San Diego route currently shows fares from €119. San Diego is an accessible destination in United States from Chicago. Mid-week departures and shoulder-season months tend to keep prices lower on this route. If this fare works, book it now - or leave an alert and we will email you if it drops.
A price alert on this page emails you if the fare to San Diego drops below a threshold you set. Searching for mid-week flights and avoiding school holiday windows can meaningfully cut costs on this route. If you're open on destination, use the interactive map from Chicago to compare San Diego against nearby alternatives - you may find a cheaper fare to a similar destination.
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Entry requirements for United States
EU passportESTA required (visa-waiver)
US passportN/A (domestic)
Requirements vary by nationality and change without notice. Check requirements for your nationality →
Alternative routes
Other ways to reach San Diego
Frequently asked questions
How much does a flight from Chicago to San Diego cost?
The cheapest fare currently available from Chicago to San Diego is €119. Prices on this route vary by season, day of week, and how far in advance you book. Click through to compare live availability for your dates before you book. Fares are refreshed regularly as our flight partners publish new availability.
Are there direct flights from Chicago to San Diego?
SkyHopp tracks both direct and connecting flights from Chicago to San Diego. Connecting flights are often priced lower but add travel time due to the layover. Whether a non-stop option exists on specific dates depends on airline schedules - use the "Direct only" filter on the interactive map to see non-stop options, or check the booking site for a full breakdown by stop count.
When is the cheapest time to fly from Chicago to San Diego?
Prices on this route typically dip during shoulder-season months, away from school holidays and public holiday windows. Mid-week departures - particularly Tuesday to Thursday - tend to be cheaper than flights on Fridays and Sundays from Chicago. Set a price alert on this page to watch the fare, or click through to compare live dates. Booking 3-6 weeks in advance generally offers the best balance of price and seat availability on this route.