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How to get fromWoburn to Chicagoby bus, plane, train (Amtrak), bus (Greyhound, Flixbus), car, or train

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There are 10 ways to get from Woburn to Chicago by bus, plane, train (Amtrak), bus (Greyhound, Flixbus), car, or train

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

  1. Line 354 bus to Boston Logan Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Pleasant St @ Woburn District Court to State St @ Washington Mall - State St Stabus bus
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    5h 21m
    $87–412

  2. Fly Boston Logan Airport to Chicago O'Hare International Airport

    cheapest
    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    5h 47m
    $72–352

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    24h 12m
    $335–707

  4. Bus

    1. Take the bus from Boston to Newark Penn Stationbus bus Greyhound US0235 / ...
    2. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus FlixBus N2641 / ...
    24h 29m
    $162–289

  5. Drive 982.1 mi

    1. Drive from Woburn to Chicagocar car 982.1 mi
    16h 54m
    $180–259

  6. Bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    6h 56m
    $101–484

  7. Train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the train from Ruggles to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    7h 41m
    $91–397

  8. Bus to Manchester Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane plane MHT - ORD
    7h 31m
    $86–414

  9. Train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Ruggles to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    8h 12m
    $76–347

  10. Fly Boston Logan Airport to General Mitchell International Airport, train

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 50m
    $685–3,376

Woburn to Chicago by bus, subway, and train (Amtrak)

Calendar7Weekly Services
Duration24h 12mAverage Duration
Ticket$335Cheapest Price
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Questions & Answers

Map of how to get from Woburn to Chicago.ExpandLaunch map view
  • Distance: 886 mi
  • Duration: 5h 21m

What companies run services between Woburn, MA, USA and Chicago, IL, USA?

Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $330–700 and the journey takes 22h 15m. Alternatively, you can take a bus from Pleasant St @ Woburn District Court to Chicago Bus Station via State St @ Washington Mall - State St Sta, Boston, and Newark Penn Station in around 24h 29m.

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