Rome2Rio

How to get fromChicago to Simsburyby subway, plane, bus, train (Amtrak), bus (Flixbus), car or bus (Greyhound)

Find Transport to Simsbury

See all options

There are 6 ways to get from Chicago to Simsbury by subway, plane, bus, train (Amtrak), bus (Flixbus), car, 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. Subway to Chicago Midway International Airport, fly, line 912 bus

    best
    1. Take the subway from Roosevelt to Midwaysubway
    2. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)planeMDW - BDL
    3. Take the bus from Central Row @ Main St to Iron Horse Park & Ride @ Jim Gallagher Waybus
    5h 54m
    $104–563

  2. Train (Amtrak)

    1. Take the train from Chicago Union Station to SpringfieldtrainLake Shore Limited
    2. Take the train from Springfield to Hartford Amtrak StationtrainAmtrak Hartford Line / ...
    22h 20m
    $153–856

  3. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York MidtownbusFlixBus N2640
    2. Take the bus from New York Midtown to Hartford Union StationbusFlixBus 2610
    25h 9m
    $129–315

  4. Drive 875.9 mi

    1. Drive from Chicago to Simsburycar875.9 mi
    15h 7m
    $160–231

  5. Fly from Chicago O'Hare International Airport, line 912 bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)planeORD - BDL
    2. Take the bus from Central Row @ Main St to Iron Horse Park & Ride @ Jim Gallagher Waybus
    6h 20m
    $144–613

  6. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus
    3. Take the bus from Port Authority Bus Terminal to Hartford Union Stationbus
    26h 58m
    $133–337

Chicago to Simsbury by train and bus (Amtrak)

Calendar7Weekly Services
Duration22h 20mAverage Duration
Ticket$153Cheapest Price
See schedules

Questions & Answers

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

You can take a train from Chicago Union Station to Iron Horse Park & Ride @ Jim Gallagher Way via Springfield, Hartford Amtrak Station, and Asylum St @ Union Pl in around 22h 20m. Alternatively, you can take a bus from Chicago Bus Station to Iron Horse Park & Ride @ Jim Gallagher Way via New York Midtown, Hartford, Union Station, and Asylum St @ Union Pl in around 25h 9m.

Transport is disrupted due to the Russia-Ukraine war. Read more

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

More Questions & Answers

Trips from Chicago

Trips to Simsbury

Popular routes