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

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There are 11 ways to get from Chicago to Waterbury by plane, bus, bus (Flixbus), train (Amtrak), 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 8m
    $114–615

  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 30m
    $84–445

  3. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from New York to New Havenbus bus
    3. Take the bus from Church St @ Chapel St to Grand St @ State Stbus bus 229
    22h 9m
    $144–246

  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 / ...
    22h 14m
    $258–569

  5. Drive  860.9 mi

    1. Drive from Chicago to Waterburycar car 860.9 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
    7h 41m
    $162–604

  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
    7h 27m
    $232–704

  8. Fly Chicago O'Hare International Airport to Westchester County Airport, line 971 bus, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from Main St @ South Broadway to Stamford Transportation Center @ Bay Abus bus
    3. Take the train from Stamford to Bridgeporttrain train
    4. Take the train from Bridgeport to Waterburytrain train
    9h 4m
    $108–494

  9. Fly Chicago O'Hare International Airport to Tweed-New Haven Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane plane ORD - HVN
    2. Take the bus from Church St @ Chapel St to Grand St @ State Stbus bus
    7h 52m
    $176–566

  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
    23h 58m
    $283–616

  11. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to New Yorkbus bus
    3. Take the train from Grand Central Terminal to Bridgeporttrain train
    4. Take the train from Bridgeport to Waterburytrain train
    25h 50m
    $186–362

Chicago to Waterbury by bus and foot

Calendar16Weekly Services
Duration22h 9mAverage Duration
Ticket$144Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Waterbury.ExpandLaunch map view
  • Distance: 831.1 mi
  • Duration: 6h 8m

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

You can take a bus from Chicago Bus Station to Grand St @ State St via New York Midtown, 8 Av/W 31 St, 8 Av/W 41 St, New York, New Haven, and Church St @ Chapel St in around 22h 9m. Alternatively, 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 14m.

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