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

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There are 10 ways to get from Waterbury to Chicago by bus, plane, train (Amtrak), bus (Flixbus), 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. Bus to Bradley International Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from W Main St @ Leavenworth St to Central Row South Side @ Travelersbus bus
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    6h 8m
    $105–614

  2. Bus to Bradley International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from W Main St @ Leavenworth St to Central Row South Side @ Travelersbus bus
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    6h 31m
    $65–344

  3. Train (Amtrak)

    1. Take the train from Meriden to Springfieldtrain train Amtrak Hartford Line / ...
    2. Take the train from Springfield to Chicago Union Stationtrain train Lake Shore Limited
    23h 16m
    $208–684

  4. Bus

    1. Take the bus from W Main St @ Leavenworth St to Asylum St @ Bushnell Parkbus bus 928
    2. Take the bus from Hartford Union Station to Times Square – 37th St.bus bus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    25h 23m
    $122–245

  5. Drive 860.1 mi

    1. Drive from Waterbury to Chicagocar car 860.1 mi
    14h 17m
    $157–227

  6. Train, train to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport to 125th Street - Harlemtrain train
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 29m
    $124–601

  7. Train, train to Laguardia Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport to 125th Street - Harlemtrain train
    3. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    7h 51m
    $74–331

  8. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h 59m
    $77–341

  9. Train via New York

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train
    23h 46m
    $234–537

  10. Train, bus

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport to Grand Central Terminaltrain train
    3. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    4. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    26h 38m
    $178–342

Waterbury to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration23h 16mAverage Duration
Ticket$208Cheapest Price
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Questions & Answers

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

You can take a bus from W Main St @ Leavenworth St to Chicago Union Station via State St @ Meriden Transit Center, Meriden, and Springfield in around 23h 16m. Alternatively, you can take a bus from W Main St @ Leavenworth St to Chicago Bus Station via Asylum St @ Bushnell Park, Hartford Union Station, Times Square – 37th St., and New York Midtown in around 25h 23m.

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