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

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There are 9 ways to get from Woburn to Chicago by plane, train (Amtrak), bus (Greyhound, Flixbus), car, bus, 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. Fly Boston Logan Airport to Chicago Midway International Airport

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    5h 26m
    $82–422

  2. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    24h 12m
    $295–657

  3. 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 N2640 / ...
    27h 49m
    $152–299

  4. Drive 982.1 mi

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

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

    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    5h 49m
    $207–512

  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
    7h 1m
    $107–575

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

    1. Take the train from South Station 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 37m
    $93–455

  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 35m
    $92–445

  9. 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 51m
    $171–826

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

Calendar7Weekly Services
Duration24h 12mAverage Duration
Ticket$295Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $290–650 and the journey takes 22h 15m.

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