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

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There are 5 ways to get from Middletown to Chicago by bus, plane, bus (Flixbus), 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. Line 55 bus, fly to Chicago Midway International Airport

    best
    1. Take the bus from Main St @ Ferry St to Main St @ 750 Main Stbus bus
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    5h 30m
    $80–393

  2. Line 55 bus, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Main St @ Ferry St to Main St @ 750 Main Stbus bus
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    6h 4m
    $70–333

  3. Bus

    1. Take the bus from Hartford Union Station to Port Authority Bus Terminalbus bus Boston
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    22h 33m
    $167–322

  4. Train (Amtrak)

    1. Take the train from Hartford Amtrak Station to Springfieldtrain train Amtrak Hartford Line / ...
    2. Take the train from Springfield to Chicago Union Stationtrain train Lake Shore Limited
    22h 54m
    $310–671

  5. Drive 883 mi

    1. Drive from Middletown to Chicagocar car 883 mi
    14h 45m
    $162–233

Middletown to Chicago by bus and foot

Calendar22Weekly Services
Duration22h 33mAverage Duration
Ticket$167Cheapest Price
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Questions & Answers

Map of how to get from Middletown to Chicago.ExpandLaunch map view
  • Distance: 814.8 mi
  • Duration: 5h 30m

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

You can take a bus from Main St @ Ferry St to Chicago Bus Station via Central Row @ Main St, Hartford Union Station, Port Authority Bus Terminal, and New York Midtown in around 22h 33m. Alternatively, you can take a bus from Silver St @ Silver St Park & Ride to Chicago Union Station via Asylum St @ Union Pl, Hartford Amtrak Station, and Springfield in around 22h 54m.

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