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

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There are 12 ways to get from Chicago to Essex by plane, bus, train, train (Amtrak), or car

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 Central Row South Side @ Travelers to Old Saybrook RR Stnbus bus
    7h 35m
    $106–517

  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 Central Row South Side @ Travelers to Old Saybrook RR Stnbus bus
    8h 5m
    $82–417

  3. Bus, train

    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 Bus Stopbus bus
    3. Take the train from New Haven to Old Saybrook Amtrak Stationtrain train
    22h 22m
    $161–288

  4. Train

    1. Take the train from Chicago Union Station to Springfieldtrain train
    2. Take the train from Springfield to New Haventrain train
    3. Take the train from New Haven to Old Saybrook Amtrak Stationtrain train
    24h 1m
    $319–658

  5. Drive 889 mi

    1. Drive from Chicago to Essexcar car 889 mi
    15h 11m
    $163–235

  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 Ny Moynihan Train Hall At Penn Station to Old Saybrook Amtrak Stationtrain train
    8h 42m
    $238–638

  7. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from Providence to Old Saybrook Amtrak Stationtrain train
    8h 28m
    $106–439

  8. Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)plane plane ORD - PVD
    2. Take the train from Providence to Old Saybrook Amtrak Stationtrain train
    8h 58m
    $90–369

  9. 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 Stamford Amtrak Station to Old Saybrook Amtrak Stationtrain train
    10h 7m
    $126–564

  10. Fly Chicago O'Hare International Airport to Tweed-New Haven Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane plane ORD - HVN
    2. Take the train from New Haven to Old Saybrook Amtrak Stationtrain train
    8h 56m
    $182–501

  11. Train via New York (Amtrak)

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Lake Shore Limited / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Old Saybrook Amtrak Stationtrain train Northeast Regional
    24h 33m
    $337–706

  12. Bus, train via Baltimore

    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 bus from Port Authority Bus Terminal to New Haven Bus Stopbus bus
    4. Take the train from New Haven to Old Saybrook Amtrak Stationtrain train
    26h 33m
    $179–401

Chicago to Essex by bus, foot, and train

Calendar32Weekly Services
Duration22h 22mAverage Duration
Ticket$161Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Essex.ExpandLaunch map view
  • Distance: 845.3 mi
  • Duration: 7h 35m

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

You can take a train from Chicago Union Station to Essex Center @ Essex Square via Springfield, New Haven, Old Saybrook Amtrak Station, and Old Saybrook Train Station Bus Shelter in around 24h 1m.

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Train operators
Bus operators

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