SAN to ORD Flight Deals: Your Guide from Sunny San Diego to the Windy City
Cheapest flight found
$92.4
Last updated Feb 16, 2026
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Tracking the May 7, 2026 departure — the cheapest date we found.
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San Diego (SAN)
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Chicago (ORD)
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Search FlightsTransitioning from the laid-back coastal vibes of Southern California to the architectural grandeur and high-energy pulse of the Midwest has never been easier than with a direct flight from San Diego International Airport to Chicago O'Hare. This iconic transcontinental route spans approximately 1,723 miles, connecting travelers with a vibrant blend of world-class dining, professional sports, and deep-dish pizza that defines the spirit of Illinois. Whether you are traveling for a high-stakes business meeting in the Loop or seeking a cultural escape to explore the Magnificent Mile and Navy Pier, booking a non-stop journey ensures you spend less time in the air and more time experiencing everything Chicago has to offer at your own pace.
Travel Tips
1. Since you are moving from a Mediterranean climate to one that is famously unpredictable, always pack layers regardless of the season, as Lake Michigan breezes can drop temperatures rapidly even on sunny days. 2. To save significant money on transportation upon arrival, consider taking the CTA Blue Line 'L' train directly from O'Hare into downtown Chicago; it is far more cost-effective than a ride-share during peak traffic hours on the Kennedy Expressway. 3. Download the mobile apps for United or American Airlines if you are flying non-stop, as they provide real-time updates on gate changes and baggage status which are frequent at busy hubs like ORD. 4. Try to book a window seat on the right side of the aircraft when approaching Chicago from the west for a potentially stunning aerial view of the skyline and the vast blue expanse of Lake Michigan.
Airport Information
San Diego (SAN)
San Diego International Airport (SAN) is uniquely situated just minutes from downtown, offering one of the most scenic takeoff and landing experiences in the United States. As a single-runway airport, it is impressively efficient, featuring two main terminals with a wide array of local dining options like Phil’s BBQ. Travelers should arrive at least two hours early during peak morning departures to navigate security comfortably.
Chicago (ORD)
Chicago O'Hare International Airport (ORD) serves as a massive global gateway and a primary hub for both United and American Airlines. Located about 17 miles northwest of the Loop, it features four active terminals and a sophisticated automated people mover system. Passengers will find an incredible variety of amenities, from high-end lounges to the famous neon-lit underground walkway connecting concourses in Terminal 1.
Seasonal Pricing Patterns
Flight prices from San Diego to Chicago typically fluctuate based on the drastic Midwestern seasons, with the highest fares occurring during the pleasant summer months of June through August and around the winter holidays. For the best value, consider traveling during the 'shoulder' seasons of late April to May or September to October. The absolute cheapest flights are generally found in January and February, provided you are willing to brave the sub-zero temperatures and potential snow delays common in the Windy City during mid-winter.
Frequently Asked Questions
How long is the flight from SAN to ORD?
A non-stop flight usually takes about 4 hours and 15 minutes, though eastbound flights may arrive slightly faster due to prevailing jet stream tailwinds.
Which airlines fly direct from San Diego to Chicago?
Major carriers including United Airlines, American Airlines, Southwest, and Alaska Airlines frequently offer non-stop service between these two major cities.
Is there a time difference between San Diego and Chicago?
Yes, Chicago is located in the Central Time Zone, which is two hours ahead of San Diego's Pacific Time Zone.
What is the best way to get to downtown Chicago from O'Hare?
The CTA Blue Line train is the most reliable and affordable option, running 24/7 and reaching the city center in approximately 45 minutes regardless of road traffic.