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

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There are 7 ways to get from Simsbury to Chicago by plane, train (Amtrak), bus (Flixbus), car, train, or bus (Greyhound)

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 Bradley International Airport to Chicago Midway International Airport

    best
    1. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)planeBDL - MDW
    5h 35m
    $100–562

  2. Train (Amtrak)

    1. Take the train from Hartford Amtrak Station to SpringfieldtrainAmtrak Hartford Line / ...
    2. Take the train from Springfield to Chicago Union StationtrainLake Shore Limited
    22h 53m
    $145–673

  3. Bus (Flixbus)

    1. Take the bus from Hartford Union Station to New York MidtownbusFlixBus 2610
    2. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    25h 33m
    $117–222

  4. Drive 875.4 mi

    1. Drive from Simsbury to Chicagocar875.4 mi
    15h 4m
    $160–231

  5. Fly Bradley International Airport to Chicago O'Hare International Airport

    1. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)planeBDL - ORD
    5h 56m
    $145–662

  6. Train to Tweed-New Haven Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Hartford Amtrak Station to New Haventrain
    2. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)planeHVN - ORD
    7h 22m
    $110–511

  7. Bus via Baltimore

    1. Take the bus from Hartford Union Station to Port Authority Bus Terminalbus
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus
    27h 40m
    $132–273

Simsbury to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration22h 53mAverage Duration
Ticket$145Cheapest Price
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Questions & Answers

What companies run services between Simsbury, CT, USA and Chicago, IL, USA?

Southwest Airlines and Delta fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, you can take a bus from Iron Horse Park & Ride @ Jim Gallagher Way to Chicago Union Station via Asylum St @ Bushnell Park, Hartford Amtrak Station, and Springfield in around 22h 53m.

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