Chicago (ORD) to San Diego (SAN) Flight Guide: Discover the Best Deals and Travel Tips

First, pack in layers because even though San Diego is known for its consistent warmth, the 'June Gloom' or coastal evening breezes can make temperatures feel quite chilly compared to the humid Chicago summer heat. Second, to maximize your first day, try to book a morning flight from O'Hare to account for the two-hour time zone difference, which effectively gives you an extra afternoon to explore Balboa Park or Coronado Island. Third, consider using the 'Blue Line' trolley extension or rideshare apps once you land at SAN; the airport is exceptionally close to downtown, making the transition from the terminal to your hotel incredibly swift. Finally, if you have TSA PreCheck, ensure it is correctly added to your boarding pass, as security lines at O'Hare's Terminal 1 and 3 can be significantly longer during peak Monday morning or Thursday afternoon business travel hours.

Flight prices between Chicago and San Diego fluctuate significantly based on the season and local events. Generally, the cheapest time to fly is during the late fall (October and November) or late winter (January and February), excluding major holidays. Conversely, prices peak during the summer months when families flock to San Diego’s beaches and during the Comic-Con international convention in July. To find the best value, travelers should aim to book at least six weeks in advance, particularly if planning a trip during the busy spring break period in March.