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

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

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 27m
    $88–462

  2. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    23h 25m
    $282–654

  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 N2641 / ...
    24h 23m
    $132–274

  4. Drive 972 mi

    1. Drive from Waltham to Chicagocar car 972 mi
    16h 39m
    $178–257

  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 45m
    $208–592

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

    1. Take the train from Back Bay to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    6h 59m
    $98–475

  7. 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 51m
    $114–581

  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 22m
    $104–501

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

    1. Take the train from Back Bay 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
    7h 26m
    $88–415

  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 47m
    $161–806

Waltham to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration23h 25mAverage Duration
Ticket$282Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $280–650 and the journey takes 22h 15m.

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