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How to get fromChicago to San Diego Countyby plane, bus (Flixbus, Greyhound), train, bus, or car

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There are 9 ways to get from Chicago to San Diego County by plane, bus (Flixbus, Greyhound), train, bus, or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly Chicago Midway International Airport to San Diego International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to San Diego International Airport (SAN)plane plane MDW - SAN
    7h 44m
    $302–995

  2. Fly Chicago O'Hare International Airport to Palm Springs International Airport, drive

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Palm Springs International Airport (PSP)plane plane ORD - PSP
    2. Drive from Indio-Palm-Springs-Airport-PSP to San Diego Countycar car
    8h 51m
    $192–404

  3. Bus

    1. Take the bus from Chicago Bus Station to St Louis Bus Stationbus bus
    2. Take the bus from St Louis Bus Station to Phoenix Bus Stationbus bus
    3. Take the bus from Phoenix Bus Station to El Cajon Transit Centerbus bus
    46h 41m
    $414–739

  4. Train, bus

    1. Take the train from Chicago Union Station to San Bernardinotrain train Southwest Chief
    2. Take the bus from San Bernardino to Escondidobus bus Lxus 2121
    46h 51m

  5. Drive 2,071.7 mi

    1. Drive from Chicago to San Diego Countycar car 2,071.7 mi
    32h 49m
    $379–547

  6. Fly Chicago O'Hare International Airport to San Diego International Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN)plane plane ORD - SAN
    8h 4m
    $252–795

  7. Train to General Mitchell International Airport, fly to San Diego International Airport

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to San Diego International Airport (SAN)plane plane MKE - SAN
    9h 7m
    $359–1,158

  8. Fly Chicago Midway International Airport to Los Angeles International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Los Angeles International Airport (LAX)plane plane MDW - LAX
    2. Take the bus from LAX Terminal 3 Shared Rides Stop to San Diegobus bus
    10h 46m
    $284–950

  9. Fly Chicago O'Hare International Airport to Los Angeles International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Los Angeles International Airport (LAX)plane plane ORD - LAX
    2. Take the bus from LAX Terminal 3 Shared Rides Stop to San Diegobus bus
    11h 1m
    $334–630

Chicago Midway International Airport (MDW) to San Diego International Airport (SAN) flights

Calendar42Weekly Planes
Duration4h 53mAverage Duration
Ticket$204Cheapest Price
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Questions & Answers

Map of how to get from Chicago to San Diego County.ExpandLaunch map view
  • Distance: 1,782.2 mi
  • Duration: 7h 44m

What companies run services between Chicago, IL, USA and San Diego County, CA, USA?

Southwest Airlines flies from Chicago Midway International Airport (MDW) to San Diego International Airport (SAN) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to San Diego County via St Louis Bus Station, Phoenix Bus Station, El Cajon Transit Center, and Maple View St & Ashwood St in around 46h 41m.

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