Boston to Chicago - 10 ways to travel via train, plane, bus, and car
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How to get fromBoston to Chicagoby plane, bus, train or car

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There are 10 ways to get from Boston to Chicago by plane, bus, 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 from Boston (BOS) to Chicago Midway (MDW)planeBOS - MDW
    best

    Flight from Boston to Chicago

    4h 13m
    $89–632
    1. Take the train from Boston to Chicago Union StationtrainLake Shore Limited
    cheapest

    Train from Boston to Chicago

    22h 22m
    $40–300
    1. Fly from Boston (BOS) to Chicago O'Hare (ORD)planeBOS - ORD

    Flight from Boston to Chicago

    4h 31m
    $59–322
    1. Take the bus from Boston to Boston Manchester Airportbus
    2. Fly from Manchester (MHT) to Chicago Midway (MDW)planeMHT - MDW

    Bus to Manchester, fly to Chicago Midway

    5h 8m
    $178–439
    1. Take the bus from Boston to Boston Manchester Airportbus
    2. Fly from Manchester (MHT) to Chicago O'Hare (ORD)planeMHT - ORD

    Bus to Manchester, fly to Chicago O'Hare

    5h 32m
    $228–519
    1. Take the train from Boston to Providencetrain
    2. Fly from Providence (PVD) to Chicago Midway (MDW)planePVD - MDW

    Train to Providence, fly to Chicago Midway

    5h 29m
    $119–849
    1. Take the train from Boston to Providencetrain
    2. Fly from Providence (PVD) to Chicago O'Hare (ORD)planePVD - ORD

    Train to Providence, fly to Chicago O'Hare

    5h 49m
    $159–1,049
    1. Fly from Boston (BOS) to Milwaukee (MKE)planeBOS - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain

    Fly Boston to Milwaukee, train

    6h 41m
    $97–518
    1. Take the bus from South Station, Boston, MA to Port Authority Bus Terminalbus
    2. Take the bus from Port Authority Bus Terminal to Indianapolis Bus Stationbus
    3. Take the bus from Indianapolis IN to Chicago ILbus

    Bus

    26h 44m
    $136–301
    1. Drive from Boston to Chicagocar989.6 mi

    Drive 989.6 mi from Boston to Chicago

    16h 30m
    $181–261

Boston to Chicago by train

Calendar7Weekly Trains
Duration22h 22mAverage Duration
Ticket$40Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Boston (BOS) to Chicago Midway (MDW) every 4 hours. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $40–300 and the journey takes 22h 22m.

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