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

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There are 8 ways to get from Chicago to Lakeville by plane, taxi, train, bus (Flixbus), car, or train (Amtrak)

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, taxi

    best
    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the taxi from Hartford-Airport-BDL to Lakevilletaxi taxi
    4h 53m
    $352–815

  2. Drive 847.7 mi

    cheapest
    1. Drive from Chicago to Lakevillecar car 847.7 mi
    14h 23m
    $155–224

  3. Train, taxi

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    2. Take the taxi from Poughkeepsie Amtrak Station to Lakevilletaxi taxi
    19h 40m
    $482–831

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from Port Authority Bus Terminal to Great Barringtonbus bus New York
    21h 52m
    $267–428

  5. Fly Chicago O'Hare International Airport to Bradley International Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the taxi from Hartford-Airport-BDL to Lakevilletaxi taxi
    5h 24m
    $328–715

  6. 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 Southeasttrain train
    3. Take the train from Southeast to Wassaictrain train
    7h 40m
    $310–703

  7. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from White Plains to Southeasttrain train
    3. Take the train from Southeast to Wassaictrain train
    8h 35m
    $200–642

  8. Train (Amtrak)

    1. Take the train from Chicago Union Station to Pittsfield Amtrak Stationtrain train Lake Shore Limited
    20h 30m
    $378–691

Chicago Midway International Airport (MDW) to Bradley International Airport (BDL) flights

Calendar41Weekly Planes
Duration3h 13mAverage Duration
Ticket$100Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Lakeville.ExpandLaunch map view
  • Distance: 833.2 mi
  • Duration: 4h 53m

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

You can take a bus from Chicago Bus Station to Lakeville via New York Midtown, Port Authority Bus Terminal, and Great Barrington in around 21h 52m. Alternatively, Amtrak operates a train from Chicago Union Station to Pittsfield Amtrak Station once daily. Tickets cost $270–600 and the journey takes 18h.

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