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

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There are 10 ways to get from Waterbury to Chicago by bus, plane, 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. 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
    5h 53m
    $85–444

  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 25m
    $75–384

  3. 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 New York Midtownbus bus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    22h 35m
    $137–231

  4. 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 14m
    $253–580

  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 9m
    $231–703

  7. Line 229 bus to Tweed-New Haven Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from W Main St @ Leavenworth St to Temple St @ New Haven Greenbus bus
    2. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    6h 32m
    $175–562

  8. Train, line 971 bus to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport to Stamfordtrain train
    3. Take the bus from Stamford Transportation Center @ Bay A to South Broadway @ Main Stbus bus
    4. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h 42m
    $123–593

  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 40m
    $276–652

  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 59m
    $159–314

Waterbury to Chicago by bus

Calendar6Weekly Buses
Duration22h 35mAverage Duration
Ticket$137Cheapest Price
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Questions & Answers

Map of how to get from Waterbury to Chicago.ExpandLaunch map view
  • Distance: 830.5 mi
  • Duration: 5h 53m

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 Bus Station via Asylum St @ Bushnell Park, Hartford Union Station, and New York Midtown in around 22h 35m. Alternatively, 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 14m.

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