Rome2Rio

How to get fromMilpitas to Chicagoby plane, bus (Flixbus, Greyhound), subway, train or car

Find Transport to Chicago

See all options

There are 8 ways to get from Milpitas to Chicago by plane, bus (Flixbus, Greyhound), subway, train, 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 Norman Y. Mineta San José International Airport to Chicago Midway International Airport

    best
    1. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago Midway International Airport (MDW)plane plane SJC - MDW
    6h 9m
    $204–958

  2. BART to San Francisco International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the subway from Milpitas to Daly Citysubway subway
    2. Fly from San Francisco International Airport (SFO) to Chicago O'Hare International Airport (ORD)plane plane SFO - ORD
    7h 32m
    $99–397

  3. Bus

    1. Take the bus from San Jose, CA - Huong Lan Sandwich to Los Angeles, CA - Chinatown Stationbus bus
    2. Take the bus from Los Angeles Downtown to Phoenix Bus Stationbus bus
    3. Take the bus from Phoenix Bus Station to St Louis Bus Stationbus bus
    4. Take the bus from St Louis Bus Station to Chicago Bus Stationbus bus
    2d 6h
    $388–705

  4. BART, train

    1. Take the subway from Milpitas to Richmondsubway subway Orange-N
    2. Take the train from Richmond to Chicago Union Stationtrain train California Zephyr
    2d 6h
    $608–1,411

  5. Drive 2,148.2 mi

    1. Drive from Milpitas to Chicagocar car 2,148.2 mi
    33h 16m
    $392–567

  6. Fly Norman Y. Mineta San José International Airport to Chicago O'Hare International Airport

    1. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago O'Hare International Airport (ORD)plane plane SJC - ORD
    6h 35m
    $124–558

  7. BART to Oakland International Airport, fly to Chicago Midway International Airport

    1. Take the subway from Milpitas to Coliseumsubway subway
    2. Fly from Oakland International Airport (OAK) to Chicago Midway International Airport (MDW)plane plane OAK - MDW
    6h 33m
    $179–815

  8. BART to San Francisco International Airport, fly to Chicago Midway International Airport

    1. Take the subway from Milpitas to Daly Citysubway subway
    2. Fly from San Francisco International Airport (SFO) to Chicago Midway International Airport (MDW)plane plane SFO - MDW
    7h 19m
    $159–677

Milpitas to Chicago by bus and foot

Calendar7Weekly Services
Duration2d 6hAverage Duration
Ticket$388Cheapest Price
See schedules

Questions & Answers

What companies run services between Milpitas, CA, USA and Chicago, IL, USA?

Southwest Airlines flies from Norman Y. Mineta San José International Airport (SJC) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a bus from Montague & Great Mall Pkwy to Chicago Bus Station via King & Tully, San Jose, CA - Huong Lan Sandwich, Los Angeles, CA - Chinatown Station, Los Angeles Downtown, Phoenix Bus Station, and St Louis Bus Station in around 2d 6h.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers

Where to next?

Trips from Milpitas

Trips to Chicago

Popular routes