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

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There are 11 ways to get from Chicago to Waterbury by plane, bus, train (Amtrak), bus (Flixbus, Greyhound), car, 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 Midway International Airport to Bradley International Airport, bus

    best
    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
    6h
    $104–615

  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
    6h 31m
    $70–395

  3. 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 / ...
    22h 13m
    $213–681

  4. 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 Grand St @ State Stbus bus 229
    25h 12m
    $130–225

  5. Drive 860.8 mi

    1. Drive from Chicago to Waterburycar car 860.8 mi
    14h 19m
    $158–227

  6. 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
    8h 23m
    $74–331

  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
    8h 5m
    $120–551

  8. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Grand Central Terminal to Bridgeporttrain train
    3. Take the train from Bridgeport to Waterburytrain train
    8h 43m
    $92–343

  9. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Newark Liberty International Airport to Bridgeport Amtrak Stationtrain train
    3. Take the train from Bridgeport to Waterburytrain train
    9h 6m
    $74–522

  10. 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
    24h 33m
    $240–534

  11. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to Bridgeporttrain train
    4. Take the train from Bridgeport to Waterburytrain train
    25h 48m
    $183–339

Chicago to Waterbury by train and bus (Amtrak)

Calendar7Weekly Services
Duration22h 13mAverage Duration
Ticket$213Cheapest Price
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Questions & Answers

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

You can take a train from Chicago Union Station to E Main St @ Phoenix St via Springfield, Meriden, and State St @ Meriden Transit Center in around 22h 13m. Alternatively, you can take a bus from Chicago Bus Station to Grand St @ State St via New York Midtown, Port Authority Bus Terminal, New Haven Union Station, and Church St @ Chapel St in around 25h 12m.

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