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How to get fromBoston to Illinoisby plane, train (Amtrak), bus (Greyhound, Flixbus), car, bus or train

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There are 8 ways to get from Boston to Illinois 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)planeBOS - MDW
    3h 26m
    $87–439

  2. Train (Amtrak)

    1. Take the train from Boston to Chicago Union StationtrainLake Shore Limited
    22h 22m
    $140–700

  3. Bus

    1. Take the bus from Boston to Newark Penn StationbusGreyhound US0235 / ...
    2. Take the bus from Newark Penn Station to Chicago Bus StationbusFlixBus N2640
    25h 30m
    $126–273

  4. Drive 980.8 mi

    1. Drive from Boston to Chicagocar980.8 mi
    16h 38m
    $179–259

  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)planeBOS - ORD
    3h 47m
    $107–310

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

    1. Take the bus from Boston to Boston Manchester Airportbus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)planeMHT - MDW
    5h 16m
    $116–583

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

    1. Take the bus from Boston to Boston Manchester Airportbus
    2. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)planeMHT - ORD
    5h 43m
    $91–443

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

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)planeBOS - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain
    5h 32m
    $291–721

Boston to Illinois by train (Amtrak)

Calendar7Weekly Trains
Duration22h 22mAverage Duration
Ticket$140Cheapest Price
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Questions & Answers

What companies run services between Boston, MA, USA and Illinois, 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 $140–700 and the journey takes 22h 22m.

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