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How to get fromChicago to Middlesboroby plane, car, bus or train

Find Transport to Middlesboro

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There are 7 ways to get from Chicago to Middlesboro by plane, car, bus, 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. Fly to Mcghee Tyson Airport, drive

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Mcghee Tyson Airport (TYS)planeORD - TYS
    2. Drive from Mcghee Tyson Airport (TYS) to Middlesborocar
    5h 15m
    $106–575

  2. Bus, drive via Dayton

    cheapest
    1. Take the bus from Chicago to Dayton Trotwood Bus Stationbus
    2. Take the bus from Dayton Trotwood Bus Station to Londonbus
    3. Drive from London to Middlesborocar
    14h 31m
    $78–266

  3. Bus, drive (Greyhound)

    1. Take the bus from Chicago Bus Station to Lexington Bus Stopbus
    2. Take the bus from Lexington Bus Stop to Londonbus
    3. Drive from London to Middlesborocar
    12h 51m
    $87–240

  4. Drive 480.7 mi

    1. Drive from Chicago to Middlesborocar480.7 mi
    8h 48m
    $88–127

  5. Fly to Asheville Regional Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Asheville Regional Airport (AVL)planeORD - AVL
    2. Drive from Asheville-Airport-AVL to Middlesborocar
    6h 35m
    $82–355

  6. Fly to Chattanooga Metropolitan Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Chattanooga Metropolitan Airport (CHA)planeORD - CHA
    2. Drive from Chattanooga Metropolitan Airport (CHA) to Middlesborocar
    6h 45m
    $192–340

  7. Train, bus, drive

    1. Take the train from Chicago Union Station to Indianapolistrain
    2. Take the bus from Indianapolis Union Station to Lexington Bus Stopbus
    3. Take the bus from Lexington Bus Stop to Londonbus
    4. Drive from London to Middlesborocar
    13h 40m
    $98–229

Chicago O'Hare International Airport (ORD) to Mcghee Tyson Airport (TYS) flights

Calendar52Weekly Planes
Duration2h 17mAverage Duration
Ticket$91Cheapest Price
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Questions & Answers

What companies run services between Chicago, IL, USA and Middlesboro, KY, USA?

There is no direct connection from Chicago to Middlesboro. However, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Mcghee Tyson Airport (TYS), then drive to Middlesboro. Alternatively, you can take a bus from Chicago Bus Station to Middlesboro via Lexington Bus Stop and London in around 12h 51m.

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