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

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There are 6 ways to get from Chicago to Middletown by plane, bus, train (Amtrak), bus (Flixbus), car, or bus (Greyhound)

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 from Chicago Midway International Airport, line 55 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 @ Gold St to Main St @ opp Ferry Stbus bus
    6h 9m
    $104–513

  2. Fly from Chicago O'Hare International Airport, line 55 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 @ Gold St to Main St @ opp Ferry Stbus bus
    6h 39m
    $80–403

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Springfieldtrain train Lake Shore Limited
    2. Take the train from Springfield to Hartford Amtrak Stationtrain train Amtrak Hartford Line / ...
    22h 19m
    $309–626

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from New York Midtown to Hartford Union Stationbus bus FlixBus 2610
    22h 31m
    $166–283

  5. Drive 883.5 mi

    1. Drive from Chicago to Middletowncar car 883.5 mi
    14h 46m
    $162–233

  6. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to Port Authority Bus Terminalbus bus
    3. Take the bus from Port Authority Bus Terminal to Hartford Union Stationbus bus
    27h 24m
    $170–330

Chicago to Middletown by train and bus (Amtrak)

Calendar7Weekly Services
Duration22h 19mAverage Duration
Ticket$309Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Middletown.ExpandLaunch map view
  • Distance: 814.2 mi
  • Duration: 6h 9m

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

You can take a train from Chicago Union Station to Silver St @ Silver St Park & Ride via Springfield, Hartford Amtrak Station, and Asylum St @ Bushnell Park in around 22h 19m. Alternatively, you can take a bus from Chicago Bus Station to Main St @ opp Ferry St via New York Midtown, Hartford Union Station, and Main St @ Gold St in around 22h 31m.

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