
San Diego, CA, USA to Chicago, IL, USA from $78: 5 ways by bus, train, flight or car
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How to Get from San Diego to Chicago: Cheapest, Fastest and Best Way
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Compare Train, Bus, Flight, and Driving Options
Get detailed, step-by-step directions below for your trip from San Diego to Chicago with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

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Traveling From San Diego to Chicago
Traveling from San Diego to Chicago offers a striking contrast between San Diego's laid-back coastal lifestyle and Chicago's vibrant urban energy.
Best Neighbourhoods in Chicago
Chicago’s neighborhoods each offer distinct charm and character for visitors.
Best Times To Visit Chicago's Attractions
Timing your visits to Chicago's attractions can elevate your experience.
Chicago Weather: What to Expect Year-Round
Chicago experiences a diverse climate with hot summers and cold winters, making spring and fall the best times to explore the city. Weather can greatly influence your travel plans, so being prepared for sudden changes ensures you enjoy everything from outdoor festivals to indoor attractions.
Dining Recommendation
Indulge in Chicago's iconic deep-dish pizza at Lou Malnati's, where the rich, buttery crust and hearty layers of cheese and toppings create a comforting experience distinct from San Diego's fresh seafood and tacos. The bustling atmosphere and dedication to local ingredients make every bite a flavorful reminder of Chicago's vibrant culinary scene.
San Diego - Chicago operators
Explore transport companies operating between San Diego and Chicago, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.
Plane from San Diego (SAN) to Chicago Midway (MDW)
Plane from San Diego (SAN) to Chicago O'Hare (ORD)
Plane from San Diego (SAN) to Chicago O'Hare (ORD)
Plane from San Diego (SAN) to Chicago O'Hare (ORD)
Bus from Santa Fe Depot, CA to Chicago Bus Station
Bus from Santa Ana Bus Stop to Las Vegas S Strip Transit Terminal
Bus from Las Vegas S Strip Transit Terminal to St Louis Bus Station
Bus from St Louis Bus Station to Chicago Bus Station
Train from San Diego to Los Angeles
Train from Los Angeles to Chicago Union Station
San Diego to Chicago: Overview of Bus, Train, Flight, and Car Trips
Traveling between San Diego and Chicago offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.
Useful tips for train travellers
Frequently asked questions
Find out more about the route from San Diego to Chicago.
Trips from San Diego
- San Diego to Irvine
- San Diego to San Clemente
- San Diego to Long Beach
- San Diego to Carlsbad
- San Diego to Riverside
- San Diego to Santa Monica
- San Diego to Pasadena
- San Diego to Newport Beach
- San Diego to Monterey
- San Diego to Mexico City
- San Diego to Santa Ana
- San Diego to Anaheim
- San Diego to Temecula
- San Diego to Albuquerque
- San Diego to Ensenada
- San Diego to San Jose
- San Diego to Los Angeles
- San Diego to San Francisco
- San Diego to San Luis Obispo
- San Diego to Bakersfield
- San Diego to Santa Barbara
- San Diego to Las Vegas
- San Diego to San Bernardino
- San Diego to San Antonio
- San Diego to Seattle
- San Diego to Yuma
- San Diego to Tijuana
- San Diego to Salt Lake City
- San Diego to Cabo San Lucas
- San Diego to Toronto
- San Diego to Miami
- San Diego to Tampa
- San Diego to Austin
- San Diego to Puerto Vallarta
- San Diego to Oceanside
- San Diego to Fort Lauderdale
- San Diego to Madrid
- San Diego to Orange
- San Diego to Avalon
- San Diego to Paris
Trips to Irvine
- Fort Wayne to Chicago
- Nashville to Chicago
- Philadelphia to Chicago
- West Lafayette to Chicago
- Boston to Chicago
- Tampa to Chicago
- Milwaukee to Chicago
- New York City to Chicago
- Detroit to Chicago
- Minneapolis to Chicago
- Pittsburgh to Chicago
- Dallas to Chicago
- Kalamazoo to Chicago
- Cleveland to Chicago
- Ann Arbor to Chicago
- Omaha to Chicago
- Memphis to Chicago
- Kansas City to Chicago
- Las Vegas to Chicago
- East Lansing to Chicago
- Columbus to Chicago
- Denver to Chicago
- Wisconsin Dells to Chicago
- Los Angeles to Chicago
- Cincinnati to Chicago
- Naperville to Chicago
- Madison to Chicago
- Saint Louis to Chicago
- Champaign to Chicago
- Grand Rapids to Chicago
- Green Bay to Chicago
- Indianapolis to Chicago
- Bloomington to Chicago
- Peoria to Chicago
- Iowa City to Chicago
- South Bend to Chicago
- Toledo to Chicago
- Rockford to Chicago
- Springfield to Chicago
- Cleveland to Chicago