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How to get fromChicago to Southburyby plane, taxi, bus (Flixbus, Greyhound), train (Amtrak), car, bus, or train

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There are 9 ways to get from Chicago to Southbury by plane, taxi, bus (Flixbus, Greyhound), train (Amtrak), 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 Chicago O'Hare International Airport to Tweed-New Haven Airport, taxi

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane plane ORD - HVN
    2. Take the taxi from New-Haven-Airport-HVN to Southburytaxi taxi
    4h 59m
    $218–570

  2. Fly Chicago O'Hare International Airport to Bradley International Airport, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the bus from Main St @ Atheneum Sq to E Main St @ Phoenix Stbus bus
    7h 57m
    $80–409

  3. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from Port Authority Bus Terminal to New Haven Union Stationbus bus
    3. Take the bus from Church St @ Chapel St to W Main St @ Waterbury Greenbus bus 229
    23h 25m
    $156–285

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Springfieldtrain train Lake Shore Limited
    2. Take the train from Springfield to Meridentrain train Amtrak Hartford Line / ...
    23h 32m
    $317–640

  5. Drive 850.5 mi

    1. Drive from Chicago to Southburycar car 850.5 mi
    14h 8m
    $156–225

  6. Fly Chicago Midway International Airport to Bradley International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the bus from Main St @ Atheneum Sq to E Main St @ Phoenix Stbus bus
    7h 26m
    $106–519

  7. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Bridgeporttrain train
    3. Take the train from Bridgeport to Waterburytrain train
    9h 2m
    $212–608

  8. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Bridgeporttrain train
    3. Take the train from Bridgeport to Waterburytrain train
    9h 22m
    $242–708

  9. Train via New York

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Bridgeport Amtrak Stationtrain train
    3. Take the train from Bridgeport to Waterburytrain train
    25h 26m
    $345–691

Chicago to Southbury by bus and foot

Calendar10Weekly Services
Duration23h 25mAverage Duration
Ticket$156Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Southbury.ExpandLaunch map view
  • Distance: 818.9 mi
  • Duration: 4h 59m

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

You can take a bus from Chicago Bus Station to Heritage Rd @ Pomperaug Woods via New York Midtown, Port Authority Bus Terminal, New Haven Union Station, Church St @ Chapel St, W Main St @ Waterbury Green, and Waterbury Green @ North Main in around 23h 25m. Alternatively, you can take a train from Chicago Union Station to Heritage Rd @ Pomperaug Woods via Springfield, Meriden, State St @ Meriden Transit Center, E Main St @ Phoenix St, and Waterbury Green @ North Main in around 23h 32m.

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